Chloramphenicol

Iupac Name：2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

CAS No.: 56-75-7

Molecular Weight：323.12938

Modify Date.: 2022-10-30 20:03

Introduction: Chloramphenicol, also known as chlornitromycin, is a broad-spectrum, bacteriostatic antibiotic derived from Streptomyces venezuelae. It is first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. The synthetic product is racemic, also called synthomycin. Syntomycin is a mixture of chloramphenicol L-isomer and d-isomer. Because of dextroisomer antibacterial effect, the effect of synthomycin is only half of the natural products. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It is effective against several gram-positive and gram-negative bacteria and commonly used in researching protein synthesis and to select for chloramphenicol-resistant transformed cells or the bacterial CAT gene.Chloramphenicol is a semisynthetic, broad-spectrum antibiotic derived from Streptomyces venequelae with primarily bacteriostatic activity. Chloramphenicol diffuses through the bacterial cell wall and reversibly binds to the bacterial 50S ribosomal subunit. The binding interferes with peptidyl transferase activity, thereby prevents transfer of amino acids to the growing peptide chains and blocks peptide bond formation. As a result bacterial protein synthesis is blocked and impede bacterial cell proliferation. View more+

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1. Names and Identifiers

1.1 Name: Chloramphenicol
1.2 Synonyms: ,[theta-(theta,theta)]- [R-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]ethanamide 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-acetamid 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-,[R-(R*,R*)]-Acetamide 2,2-dichloro-n-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-acetamid Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl) Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]- Acetamide, 2,2-dichloro-N-[beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)- Ambofen CAF Catilan Chlomin chloroamphenicol D-()-threo-1-p-nitrophenyl-2-dichloracetamido-1,3-propanediol EINECS 200-287-4 Enicol i337a MFCD00078159 Mychel u-6062

1.3 CAS No.: 56-75-7

1.4 CID: 5959

1.5 EINECS(EC#): 200-287-4

1.6 Molecular Formula: C11H12Cl2N2O5 (isomer)

1.7 Inchi: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

1.8 InChkey: WIIZWVCIJKGZOK-RKDXNWHRSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

1.10 Isomers Smiles: C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

2. Properties

2.1 Density: 1.547

2.1 Melting point: 149-153℃

2.1 Boiling point: 644.9 oC at 760 mmHg

2.1 Refractive index: 20 ° (C=5, EtOH)

2.1 Flash Point: 343.8 oC

2.1 Precise Quality: 322.01200

2.1 PSA: 115.38000

2.1 logP: 1.82310

2.1 Solubility: absolute ethanol: soluble5-20mg/mL (as a stock solution)

2.2 Appearance: white to off-white crystalline powder

2.3 Storage: Store at -20°C.

2.4 Carcinogenicity: Chloramphenicol is reasonably anticipated to be a human carcinogen, based on limited evidence of carcinogenicity from studies in humans.

2.5 Color/Form: Powder

2.6 Contact Allergens: This broad spectrum phenicol group antibiotic has beenimplicated in allergic contact dermatitis. Cross-sensitivityto thiamphenicol is possible, but not systematic.

2.7 Decomposition: When heated to decomposition it emits very toxic fumes of /nitrogen oxides and chloride/.

2.8 PH: Neutral to litmus

2.9 pKa: 11.03±0.46(Predicted)

2.10 Water Solubility: 2.5 g/L (25 o C)

2.11 Spectral Properties: Specific optical rotation: +18.6 deg @ 20 deg C/D (c= 4.86 in ethanol); -25.5 deg @ 25 deg C/d (ethyl acetate).
IR: u 5174 (Coblentz Society spectral collection)
UV: 385 (Adsorption Spectra in the UV and Visible Region, Academic Press, New York)
MASS: 236 (The Aldrich Handbook of Organic Chemicals and Biochemicals, Aldrich Chemical Co., Inc., Aldrich Chemical Co., Milwaukee, WI)

2.12 Stability: Stable under normal shipping and handling conditions.

2.13 StorageTemp: Keep in dark place,Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.

3.2 Potential Exposure: An antibiotic derived from streptomyces venezuelae. A potential danger to those involved in themanufacture, formulation, and application of this antibioticand antifungal agent

3.3 Purification Methods: Purify chloramphenicol by recrystallisation from H2O (solubility is 2.5mg/mL at 25o) or ethylene dichloride as needles or long plates, and by sublimation at high vacuum. It has A 1cm 298 at max 278nm, and it is slightly soluble in H2O (0.25%) and propylene glycol (1.50%) at 25o but is freely soluble in MeOH, EtOH, BuOH, EtOAc and Me2CO. [Relstock et al. J Am Chem Soc 71 2458 1949, Confroulis et al. J Am Chem Soc 71 2463 1949, Long & Troutman J Am Chem Soc 71 2469, 2473 1949, Ehrhart et al. Chem Ber 90 2088 1957, Beilstein 13 IV 2742.]

3.4 Shipping: UN3249 Medicine, solid, toxic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxicsolids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

3.5 Usage: Chloramphenicol is used for the treatment caused by typhoid bacillus, dysentery bacillus, Escherichia coli, bacillus, influenza and pneumococcal infections such as brucellosis.Chloramphenicol is used in the treatment of infections caused by bacteria. It works by killing bacteria or preventing their growth.Chloramphenicol is used to treat serious infections in different parts of the body. It is sometimes given with other antibiotics. However, chloramphenicol should not be used for colds, flu, other virus infections, sore throats or other minor infections, or to prevent infections.Chloramphenicol should only be used for serious infections in which other medicines do not work. This medicine may cause some serious side effects, including blood problems and eye problems. Symptoms of the blood problems include pale skin, sore throat and fever, unusual bleeding or bruising, and unusual tiredness or weakness.You and your doctor should talk about the good this medicine will do as well as the risks of taking it .Chloramphenicol is available only with your doctor's prescription.

3.6 Waste Disposal: It is inappropriate and possiblydangerous to the environment to dispose of expired or wastepharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired orwaste pharmaceuticals may be mixed with wet cat litter orcoffee grounds, double-bagged in plastic, discard in trash.Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return thepharmaceutical to the manufacturer for proper disposal beingcareful to properly label and securely package the material.Alternatively, the waste pharmaceutical shall be labeled,securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. Chloramphenicol Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R45

4.1 Safety Statements: S45;S53

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl chloramphenicol sodium succinate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Chloramphenicol sodium succinate/
Oral dosage form new animal drugs. Chloramphenicol tablets. Conditions of use: dogs ... Indications for use: Oral treatment of bacterial pulmonary infections, bacterial infections of the urinary tract, bacterial enteritis, and bacterial infections associated with canine distemper caused by susceptible organisms.
Oral dosage form new animal drugs. Chloramphenicol capsules. Conditions of use: dogs ... Indications for use: Oral treatment of bacterial pulmonary infections, bacterial infections of the urinary tract, bacterial enteritis, and bacterial infections associated with canine distemper caused by susceptible organisms.
Oral dosage form new animal drugs. Chloramphenicol palmitate oral suspension. Conditions of use: dogs ... Indications for use: Treatment of bacterial pulmonary infections, infections of the urinary tract, enteritis, and infections associated with canine distemper that are caused by organisms susceptible to chloramphenicol. /Chloramphenicol palmitate/
Implantation or injectable dosage form new animal drugs. Chloramphenicol injection. Conditions of use: dogs ... Indications for use: Treatment of infections of the respiratory tract, the urinary tract, and enteritis and tonsillitis caused by organisms susceptible to chloramphenicol.
Ophthalmic and topical dosage form new animal drugs. Chloramphenicol ophthalmic ointment. Conditions of use: dogs and cats ... Indications for use: Treatment of bacterial conjunctivitis caused by pathogens susceptible to chloramphenicol.
Ophthalmic and topical dosage form new animal drugs. Chloramphenicol ophthalmic solution. Conditions of use: dogs and cats ... Indications for use: Treatment of bacterial conjunctivitis caused by organisms susceptible to chloramphenicol.
Ophthalmic and topical dosage form new animal drugs. Chloramphenicol-prednisolone ophthalmic ointment. Conditions of use: dogs and cats ... Indications for use: Treatment of bacterial conjunctivitis and ocular inflammation caused by organisms susceptible to chloramphenicol.
Extralabel drug use in animals. Drugs prohibited for extralabel use in animals. The following drugs, families of drugs, and substances are prohibited for extralabel animal and human drug uses in food-producing animals. Chloramphenicol is included on this list.

4.2 Octanol/Water Partition Coefficient: log Kow = 1.14

4.3 Other Preventative Measures: PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

4.4 Hazard Class: IRRITANT

4.4 Hazard Declaration: H350

4.4 Cleanup Methods: PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

4.5 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

4.6 RIDADR: UN 1851

4.6 Safety Profile: Confirmed human carcinogen producing leukemia, aplastic anemia, and other bone marrow changes. Experimental tumorigenic data. Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by an unknown route: changes in plasma or blood volume, unspecified liver effects, and hemorrhaging. Experimental teratogenic and reproductive effects. Human mutation data reported. An antibiotic. When heated to decomposition it emits very toxic fumes of NOx and Cl-. See also other chloramphenicol entries.

4.7 Caution Statement: P201-P280-P308 + P313

4.7 Formulations/Preparations: Ophthalmic: For solution: 25 mg Chloromycetin Ophthalmic (with 15 mL sterile water diluent), (Monarch); Ointment: 1% Chloramphenicol Ophthalmic Ointment, (King), Chloromycetin Ophthalmic, (Monarch), Chloroptic S.O.P. (with chlorobutanol 0.5%), (Allergan), Ocu-Chlor, (Ocumed); Solution: 0.5% Chloroptic (with chlorobutanol 0.5%), (Allergan), Ocu-Chlor, (Ocumed).
Otic: Solution: 0.5% Chloromycetin Otic (with propylene glycol), (Monarch).
Chloramphenicol is often formulated as the cinnamate, palmitate (1.7 g equivalent to 1.0 g chloramphenicol) or sodium succinate salt ... . Preparations are available as capsules (50, 100 and 250 mg; USP grade contains 90-120% of the labelled amt of ai), ear drops (soln in propylene glycol), eye drops (0.5% soln or sterile, dry mixture of chloramphenicol and suitable buffers containing 90-130% of the labelled amt of chloramphenicol ... ); and as the palmitate in a suspension for oral administration (USP 5 ml, 30 mg/ml, containing 90-120% of the labelled amt of ai) and the succinate in vials of 1 g for injection (USP grade containing 90-115% of the labelled amt of ai).

4.8 Incompatibilities: Compounds of the carboxyl group reactwith all bases, both inorganic and organic (i.e., amines),releasing substantial heat, water, and a salt that may beharmful. Incompatible with arsenic compounds (releaseshydrogen cyanide gas), diazo compounds, dithiocarbamates,isocyanates, mercaptans, nitrides, sulfides (releasing heat,toxic, and possibly flammable gases), thiosulfates, anddithionites (releasing hydrogen sulfate and oxides of sulfur).

4.9 WGK Germany: 3

4.9 RTECS: AB6825000

4.9 Report: ?Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.10 Safety: ?Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by an unknown route: changes in plasma or blood volume, unspecified liver effects, and hemorrhaging. Experimental teratogenic and reproductive effects. Human mutation data reported. An antibiotic. When heated to decomposition it emits very toxic fumes of NO_x and Cl^?.
Hazard Codes:?T
Risk Statements: 45?
R45:May cause cancer.
Safety Statements: 53-45?
S53:Avoid exposure - obtain special instructions before use.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 2811
WGK Germany: 3
RTECS of Chloramphenicol (CAS NO.56-75-7): AB6825000

4.11 Specification: ? Chloramphenicol (CAS NO.56-75-7), its Synonyms are Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,R*))- ; Alficetyn ; Ambofen ; Amphenicol ; Amphicol ; Amseclor ; Chlomin ; Chlomycol ; Chlora-tabs ; Chloramex ; Chloramfenikol ; Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (theta-(theta,theta))- ; Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo- . It is white to grey-white crystalline powder.

4.12 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	unreported	250mg/kg/10D (250mg/kg)	LIVER: OTHER CHANGES BLOOD: HEMORRHAGE BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Clinical Pediatrics Vol. 14, Pg. 499, 1975.
dog	LD	intramuscular	> 101mg/kg (101mg/kg)	?	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog	LD	oral	> 300mg/kg (300mg/kg)	?	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog	LDLo	intravenous	150mg/kg (150mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of Bacteriology. Vol. 55, Pg. 425, 1948.
guinea pig	LD50	intravenous	560mg/kg (560mg/kg)	?	Farmaco, Edizione Scientifica. Vol. 9, Pg. 21, 1954.
guinea pig	LD50	oral	500mg/kg (500mg/kg)	?	Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
infant	LDLo	intravenous	30mg/kg/3D-I (30mg/kg)	CARDIAC: CARDIAC OUTPUT VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Pediatrics. Vol. 103, Pg. 487, 1983.
infant	LDLo	unreported	200mg/kg/4D-I (200mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" BLOOD: EOSINOPHILIA	Lancet. Vol. 1, Pg. 555, 1986.
infant	TDLo	intramuscular	250mg/kg/2D (250mg/kg)	VASCULAR: CHANGE IN PLASMA OR BLOOD VALUME	New England Journal of Medicine. Vol. 262, Pg. 787, 1960.
infant	TDLo	oral	440mg/kg (440mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES	JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.
mouse	LD50	intraperitoneal	1100mg/kg (1100mg/kg)	?	Dissertationes Pharmaceuticae. Vol. 14, Pg. 21, 1962.
mouse	LD50	intravenous	110mg/kg (110mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
mouse	LD50	oral	1500mg/kg (1500mg/kg)	?	Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse	LD50	subcutaneous	400mg/kg (400mg/kg)	?	"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 493, 1978.
rabbit	LD50	intravenous	117mg/kg (117mg/kg)	?	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat	LD50	intraperitoneal	1811mg/kg (1811mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat	LD50	intravenous	171mg/kg (171mg/kg)	?	Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat	LD50	oral	2500mg/kg (2500mg/kg)	?	Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
rat	LD50	subcutaneous	5gm/kg (5000mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.
women	LDLo	oral	400mg/kg (400mg/kg)	BEHAVIORAL: COMA VASCULAR: SHOCK LUNGS, THORAX, OR RESPIRATION: CYANOSIS	JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 1A

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H350 May cause cancer
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Other Information

7.0 Merck: 14,2077

7.1 BRN: 2225532

7.2 Description: Chloramphenicol, also known as chlornitromycin, is a broad-spectrum, bacteriostatic antibiotic derived from Streptomyces venezuelae. It is first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. The synthetic product is racemic, also called synthomycin. Syntomycin is a mixture of chloramphenicol L-isomer and d-isomer. Because of dextroisomer antibacterial effect, the effect of synthomycin is only half of the natural products. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It is effective against several gram-positive and gram-negative bacteria and commonly used in researching protein synthesis and to select for chloramphenicol-resistant transformed cells or the bacterial CAT gene.
Chloramphenicol is a semisynthetic, broad-spectrum antibiotic derived from Streptomyces venequelae with primarily bacteriostatic activity. Chloramphenicol diffuses through the bacterial cell wall and reversibly binds to the bacterial 50S ribosomal subunit. The binding interferes with peptidyl transferase activity, thereby prevents transfer of amino acids to the growing peptide chains and blocks peptide bond formation. As a result bacterial protein synthesis is blocked and impede bacterial cell proliferation.

7.3 Chemical Properties: It is white or yellowish green needle like crystals. The melting point is 150.5-151.5℃ (149.7-150.7℃). Under the high vacuum it can be sublimated, slightly soluble in water (2.5mg/ml at 25℃), slightly soluble in propylene glycol (150.8mg/ml), soluble in methanol, ethanol, butanol, ethyl acetate, acetone, insoluble in ether, benzene, petroleum ether, vegetable oil. Taste is very bitter.

7.4 Uses

Chloramphenicol is used for the treatment caused by typhoid bacillus, dysentery bacillus, Escherichia coli, bacillus, influenza and pneumococcal infections such as brucellosis.
Chloramphenicol is used in the treatment of infections caused by bacteria. It works by killing bacteria or preventing their growth.
Chloramphenicol is used to treat serious infections in different parts of the body. It is sometimes given with other antibiotics. However, chloramphenicol should not be used for colds, flu, other virus infections, sore throats or other minor infections, or to prevent infections.
Chloramphenicol should only be used for serious infections in which other medicines do not work. This medicine may cause some serious side effects, including blood problems and eye problems. Symptoms of the blood problems include pale skin, sore throat and fever, unusual bleeding or bruising, and unusual tiredness or weakness.

You and your doctor should talk about the good this medicine will do as well as the risks of taking it .
Chloramphenicol is available only with your doctor's prescription.

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7.5 Antimicrobial Spectrum

Chloramphenicol is bacteriostatic and a broad-spectrum antibiotic active against both gram-positive and gram-negative bacteria including rickettsia (cause of rocky-mountain spotted fever) and chlamydia. It is also found effective against Haemophilus influenzae causing meningitis.

Gram-positive: Streptococcus spp., Staphylococcus spp., Enterococcus spp., Bacillus anthracis, Listeria monocytogenes.
Gram-negative: Hemophilus influenzae, M. catarrhalis, N. meningitides, E. coli, P. mirabilis, Salmonella spp., Shigella spp., Stenotrophomonas maltophilia.

7.6 Mechanism of action: Inhibition of protein synthesis, Chloramphenicol irreversibly binds to a receptor site on the 50S subunit of the bacterial ribosome, inhibiting peptidyl transferase. This inhibition consequently results to the prevention of amino acid transfer to growing peptide chains, ultimately leading to inhibition of protein formation.

7.7 Pharmacokinetics: After oral administration, it is rapidly and completely absorbed, can be widely distributed in body tissues and body fluids. In the cerebrospinal fluid concentration distribution were higher than other antibiotics, oral bioavailability was 75%~90%. After oral half hour of in the blood can reach the effective concentration, It can reach the peak in 2 to 3 hours. Take oral 0.5g, 1g and 2g, blood drug concentration was 4mg/L, 8~10mg/L and 16~21mg/L in 2 hours, 1~2g, 4 times a day, can make the blood to maintain long-term effective concentration of 10mg/L~5. After intravenous injection, the average is similarity with oral blood drug concentration of the same dose. After intramuscular absorption is slow and irregular, blood concentration is only oral amounts of 50%, but the maintenance time is long. The plasma protein binding rate is 50%~60%., the half-life of 2 to 3 hours, the half-life of newborns was significantly higher than that of adults, under the age of 2 is about 24 hours, 2 to 4 years is about 12 hours. This product is absorbed and widely distributed in the body each Reduce the concentrations of blood concentration in the blood to body fluids and tissues of liver and kidney was the highest, followed by the lung, spleen, heart, intestine and brain. Bile content is low, about 20%~50%, but also can enter the pleural effusion and ascites, milk, fetal circulation and ocular tissue. Through the blood brain barrier to reach the cerebrospinal fluid (CSF), in normal cerebrospinal fluid (CSF) in concentrations is up to 20%~50%, inflammation is up to 50%~100%. It is mainly in the liver metabolism, binding with glucuronic acid to inactivation, about 75%~90% of the metabolites in 24 hours urine, of which 5%~15% for the prototype drug. 1 g orally, urine concentration is 70~150mg/L. serious liver disease patients, the half-life may be extended due to hepatic metabolism and poisoning caused by accumulation.

7.8 Indications: This product is fat soluble, synthetic peptide can inhibit the formation and prevent protein. Is a bacteriostatic agent, high concentration or effect highly sensitive to the bacteria to this product showed bactericidal action. This product is applicable to the general application of typhoid and paratyphoid salmonella, and other Bacteroides fragilis.
1. Chloramphenicol is the preferred treatment of typhoid and paratyphoid fever, and can be used for typhoid Salmonella infections.
2. Used for pneumococcal in patients allergic to penicillin, ampicillin B Hib meningitis or tolerance, meningococcal meningitis, sensitive to the change of gram negative bacilli meningitis.
3. Used for aerobic and anaerobic bacteria mixed infection of otogenic brain abscess.
4. Used for serious anaerobic infections, such as Bacteroides fragilis infection.
5. Used as aminoglycoside drugs in the treatment of infection caused by sensitive bacteria and other microorganisms, such as influenza bacillus, Salmonella and other gram negative bacilli to sepsis, pulmonary infection.
6. Used for the local treatment of flu from Escherichia coli, bacillus, Klebsiella pneumoniae, Staphylococcus aureus, Streptococcus and eye, ear superficial infection.
7. It is effective for Rickettsia, mycoplasma, and infection.
8. Coli and Serratia of Pseudomonas aeruginosa is infections.
9. Chloramphenicol eye drops for the treatment of infections caused by sensitive bacteria caused by the eye, such as trachoma, conjunctivitis, keratitis, blepharitis etc..
10. This medicine local ear drops can be used for treating sensitive bacteria infections caused by otitis externa, acute and chronic otitis media, the drug ear plugs can also be for inflammation of the ear canal and radical mastoidectomy postoperative oozing pus.

7.9 resistance: Drug resistance of gram negative bacilli on chloramphenicol acetyltransferase, mostly due to drug inactivation, the enzyme is mediated by the R factor. Drug resistance of gram positive bacteria, may also be due to similar mechanisms, but not fully clear. Some strains of Pseudomonas aeruginosa and Proteus, Klebsiella, are another way to generate drug resistance, which prompted the permeability change, and chloramphenicol cannot enter the cell.
Bacterial resistance to chloramphenicol resistant strains both in vitro and in vivo, increased gradually in recent years. Escherichia coli, Salmonella and other gram negative bacilli can be due to drug resistance factor factor (R) transfer and acquire resistance. It has been proven that with R factor of Escherichia coli can produce acetyl transferase, chloramphenicol acetylation of failure; chloramphenicol resistant Staphylococcus aureus can also produce some inducible enzyme, under the participation of acetyl CoA, the acetylation of chloramphenicol.

7.10 Drug interactions: Chloramphenicol inhibits hepatic microsomal enzyme of phenytoin and tolbutamide (Jia Tangning) and chlorpropamide and dicoumarol (and possibly other drug metabolism, and the prolonged in vivo half-life, increased concentrations of serum. Poisoning aggravate that death is also reported. On the other side, phenobarbital, phenytoin, rifampin (are, 1985) can decrease the serum concentration of chloramphenicol, which was estimated to be due to the inductive effect of drugs on the liver enzymes. Therefore, at the same time, the application effect of chloramphenicol pharmacokinetics of drugs, should be paid attention to the monitoring of serum concentration of chloramphenicol.
Chloramphenicol can delay the iron, folic acid and vitamin B12 on anemia treatment response. It can interfere with the host to tetanus toxoid anamnestic response. Therefore, at the same time, the application situation chloramphenicol and active immune agents should be avoided.
Antagonistic effects of chloramphenicol on penicillin bactericidal effect, which is verified in vitro and animal experiments, but its clinical significance is not clear. This kind of combination, only in the proof of such treatment is benefit, began to be used.

7.11 Adverse reactions and precautions: 1. Inhibition of bone marrow hematopoietic function: for the most serious toxicity of chloramphenicol, such as red blood cells, granulocyte and platelet reduce. There are two types: one is the reversible inhibition, manifested as neutropenia and thrombocytopenia, and anemia, related to dose and duration can be gradually recovered after drug withdrawal; Second is irreversible aplastic anemia, with dosage and duration without direct relationship, low incidence, once often occur difficult to reverse, high mortality rate and a few survivors can development for granulocytic leukemia, women, children, and liver and kidney function not entire occurrence rate is high. This is the main reason to limit the clinical application.
2. In the liver, metabolism rate of this product is very high, on the function of the liver, it has impaired the appropriate quantity (adult day not more than 1 g) or not as much as possible.
3. Chloramphenicol is only 5%~10% prototype drug discharge from the kidney, it is not appropriate for the treatment of urinary tract infection.
4. Premature infants and neonatal as much as possible.
5. I see the spirit of neurological symptoms, should be promptly discontinued.
6. During late pregnancy and lactation are not suitable for this application, because this product in vivo is conjugated with glucuronic acid and detoxification, conjugates excreted by the kidneys. And this product can be through the placenta to the fetus, fetal and neonatal, due to not perfect of enzyme system in the liver, glucuronic acid combined with the ability is poor and excretory function of the kidney is weak. Therefore, it is very easy to cause drug accumulation, the newborn gray baby syndromes. Gray cyanosis, dyspnea, vomiting, abdominal distension and circulatory failure with unique performance, high fatality rate. In addition, this product can damage the hematopoietic system, can make the pregnant women aplastic anemia, neonatal thrombocytopenia and other consequences.

7.12 Methods of production: Methods for producing countries in the world to chloramphenicol had a lot of research, summed up: (1) p-nitroacetophenone method; (2) styrene method; (3) Cinnamyl alcohol method; (4) The nitro cinnamic alcohol method; (5) P-nitrobenzaldehyde method. China use p-nitroacetophenone method, the method is by ethylbenzene via nitration, oxidation, bromide, salt, hydrolysis, acetylation, addition, reduction, decomposition, split second chloride acetylation and chloramphenicol.

7.13 Description: Chloramphenicol was originally produced by fermentation of Streptomyces venezuelae, but its comparatively simple chemical structure soon resulted in several efficient total chemical syntheses. With two asymmetric centers, it is one of four diastereomers, only one of which (1R,2R) is significantly active. Because total synthesis produces a mixture of all four, the unwanted isomers must be removed before use. Chloramphenicol is a neutral substance that is only moderately soluble in water, because both nitrogen atoms are nonbasic under physiologic conditions (one is an amide and the other a nitro moiety). It was the first broad-spectrum oral antibiotic used in the United States and was once very popular. Severe potential blood dyscrasia has greatly decreased its use in North America. Although its cheapness and efficiency makes it still very popular in much of the rest of the world where it can often be purchased over-the-counter without a prescription

7.14 Chemical Properties: White to grey-white crystalline powder

7.15 Chemical Properties: Chloramphenicol is a white to grayish-white or yellowish-white crystalline solid.

7.16 Originator: Leukomycin,Bayer,W. Germany

7.17 Uses: antibacterial, antirickettsial, inhibits protein synthesis

7.18 Uses: Chloramphenicol is unusual nitroaromatic metabolite produced by Streptomyces venezuelae, first published in 1947. Chloramphenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Although restricted to ocular use, antibiotic resistance to other classes has refocused attention on this class. Chloramphenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Chloramphenicol has been extensively studied with over 35,000 literature citations.

7.19 Uses: Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial

7.20 Definition: ChEBI: An organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions.

7.21 Indications: Resistance to chloramphenicol is usually explained by the presence of a plasmid that determines the production of chloramphenicol acetyltransferase. This enzyme acetylates the drug, giving it unable to bind with 50 S subunits of bacterial ribosomes.
Chloramphenicol is a potentially toxic drug and has a few indications for use. It is the drug of choice for treating typhoid fever, and it is used for treating brain abscesses. Until recently, it was the drug of choice for therapy of bacterial meningitis in children (in combination with ampicillin). However, third-generation cephalosporins are currently preferred for such purposes. Chloramphenicol is an effective alternative for a number of infections in situations, where drugs of choice cannot be used for one reason or another. However, it should never be used for infections that can readily be treated with other antimicrobial drugs. Synonyms of this drug are levomycetin, amindan, aquamycetin, chloromycetin, ophthoclor, opulets, leukomycin, and many others.

7.22 Manufacturing Process: Chloramphenicol may be prepared by fermentation or by chemical synthesis. The fermentation route to chloramphenicol is described in US Patents 2,483,871 and 2,483,892. To quote from US Patent 2,483,892: The cultivation of Streptomyces venezuelae may be carried out in a number of different ways. For example, the microorganism may be cultivated under aerobic conditions on the surface of the medium, or it may be cultivated beneath the surface of the medium, i.e., in the submerged condition, if oxygen is simultaneously supplied.
Briefly stated, the production of chloramphenicol by the surface culture method involves inoculating a shallow layer, usually less than about 2 cm, of a sterile, aqueous nutrient medium with Streptomyces venezuelae and incubating the mixture under aerobic conditions at a temperature between about 20° and 40°C, preferably at room temperature (about 25°C), for a period of about 10 to 15 days. The mycelium is then removed from the liquid and the culture liquid is then treated by methods described for isolating therefrom the desired chloramphenicol. The synthetic route to chloramphenicol is described in US Patent 2,483,884 as follows: 1.1 g of sodium is dissolved in 20 cc of methanol and the resulting solution added to a solution of 5 g of benzaldehyde and 4.5 g of betanitroethanol in 20 cc of methanol. After standing at room temperature for a short time the gel which forms on the mixing of the reactants changes to a white insoluble powder. The precipitate is collected, washed with methanol and ether and then dried. The product thus produced is the sodium salt of 1- phenyl-2-nitropropane-1,3-diol.
Eighteen grams of the sodium salt of 1-phenyl-2-nitropropane-1,3-diolis dissolved in 200 cc of glacial acetic acid. 0.75 g of palladium oxide hydrogenation catalyst is added and the mixture shaken at room temperature under three atmospheres pressure of hydrogen overnight. The reaction vessel is opened, 2.5 g of 10% palladium on carbon hydrogenation catalyst added and the mixture shaken under three atmospheres pressure of hydrogen for 3 hours. The catalyst is removed from the reaction mixture by filtration and the filtrate concentrated under reduced pressure. Fifty cubic centimeters of npropanol is added to the residue and the insoluble inorganic salt removed by filtration.
The filtrate is treated with excess hydrochloric acid and evaporated to obtain a pale yellow oil. Five grams of the oil thus obtained is treated with 15 cc of saturated potassium carbonate solution and the mixture extracted with 50 cc of ether, then with 30 cc of ethyl acetate and finally with two 30 cc portions of ethanol. Evaporation of the solvent from the extract gives the following quantities of the desired 1-phenyl-2-aminopropane-1,3-diol: 0.5 g, 1.0 g and 3.1 g.
1.7 g of 1-phenyl-2-aminopropane-1,3-diol is treated with 1.6 g of methyl dichloroacetate and the mixture heated at 100°C for 1.25 hours. The residue is washed with two 20 cc portions of petroleum ether and the insoluble product collected. Recrystallization from ethyl acetate yields the desired (dl)- reg.-1-phenyl-2-dichloroacetamidopropane-1,3-diol in pure form; MP 154° to 156°C.Five hundred milligrams of (dl)-reg.-1-phenyl-2-dichloroacetamidopropane- 1,3-diolis added to a solution consisting of 1 cc of pyridine and 1 cc of acetic anhydride and the resulting reaction mixture heated at 100°C for 1/2 hour. The reaction mixture is evaporated to dryness under reduced pressure and the residue taken up in and crystallized from methanol. Recrystallization from methanol produces the pure diacetate of (dl)-reg.-1-phenyl-2-dichloroacetamidopropane-1,3-diol (MP 94°C). Two hundred milligrams of the diacetate of (dl)-reg.-1-phenyl-2- dichloroacetamidopropane1,3-diol is added to a mixture consisting of 0.25 cc of concentrated nitric acid and 0.25 cc of concentrated sulfuric acid at 0°C. The reaction mixture is stirred until solution is complete, poured onto 25 g of ice and the mixture extracted with ethyl acetate. The ethyl acetate extracts are evaporated under reduced pressure and the diacetate of (dl)-reg.-1- pnitrophenyl-2-dichloroacetamidopropane-1,3-diol so produced purified by recristallization from ethanol; MP 134°C.
Five hundred milligrams of the diacetate of (dl)-reg.-1-p-nitrophenyl-2- dichloroacetamidopropane-1,3-diol is dissolved in a mixture consisting of 25 cc of acetone and an equal volume of 0.2 N sodium hydroxide solution at 0°C and the mixture allowed to stand for one hour. The reaction mixture is neutralized with hydrochloric acid and evaporated under reduced pressure to dryness. The residue is extracted with several portions of hot ethylene dichloride, the extracts concentrated and then cooled to obtain the crystalline (dl)-reg.-1- p-nitrophenyl-2-dichloroacetamidopropane-1,3-diol; MP 171°C.

7.23 Brand name: Chloromycetin (Parke-Davis);Acne-sol;Acnoxin;Actimac;Actinac;Alficetyn susp.;Altabactin;Ambrasynth;Amphemycin-prednisonum;Ampliomicetin;Amseclim;Angimidone;Angiters;Antibiopto;Aquapred;Armacol;Arrlicetin;Aviatrin;Balkamycin;B-cpct;Bemacol;Berlicetin;Biofeniol;Biophtas;Biotocap;Bismophenyl;Bitencyl;C. o fluo-fenicol;C. o hidrocor-clora;Cafenolo;Calmina;Campiol;Caosol;Cavumycetina;Ccombinado balsamico;Ccorticol;Cebenicol;Chemibal;Chemyzin;Chloramfenicol;Chloramol;Chloramphenicol intervetra;Chloramphenicol-pos;Chloramphycin;Chloramplast;Chloramson;Chloranfeni-mck;Chloranfeni-opipno;Chloranfeni-otico;Chloranfeni-ungena;Chloreptic;Chlorical;Chloroantibion;Chlorocortal;Chlorofair;Chloroject s;Chloromex;Chloromik;Chloromimyxin;Chloromycetin kapseals;Chloromycetin palmitate;Chloroptic p. oint.;Chlorostrep;Clorbiotina;Clorbis supp.;Cloromicetin;Cloromycetin;Cloroptic farmicetina;Clorosyntex;Colidene;Colimy-c;Cortican;Cortidermale;Cortimisin;Cortiphenicol;Cortison-quemicet;Cortivert;Cutispray no. 4;Cyphenicol;Cysticat;Davuron sedante;Dectamicina;Delta optil;Devamycetin;Dexa-biofinicol;Dorsec;Duphenicol;Econoclor;Ejificol strept;Ejificol sulfa;Elase chloromycel;Enttocetrin;Erittronicol;Erteilen;Esterofenil;Estevecicina cloranfenico;Extracicilina;Fago-praxin;Fluorobioptal;Furacol l;Furamecetil alpha magna;Furamecetil magna;Furatrimon;Furokatin;Gammaphenicol;Ginetris;Gino-dectacil;Gliscol;Globveticol;Goticas;Nova-phenicol;Novoclorocap;Oftan;Ophthaphenicol;Opthalon;Oralmisetin;Otiprin;Otopred ear drops;Pantofenicol;Parcyclin;Pedimycetin;Pentocetina;Pertaril;Pimabiciron;Pinimentac;Plastoderma;Prednomycetine;Procusulf;Protercicline;Prurivet;Pulmo vinco;Quitrase antibiotico;Ranphenicol;Ranstrepcol;Reclor;Redidropsol;Renegen;Reocetin;Reostop;Rheofin;Rivomycin sulfa;Rolintrex;Roncovita;Ronphenil;Roscomycin;Rovictor;Samaphenicol;Scanicoline;Scieramycetin;Sergo-amigdalar;Serviclofen;Sigmicilina;Sintomitsin;Snophenicol;Soludectancil;Sopamycetin;Spasmo-paraxin;Spersanicol;Strepticine;Streptoglobenicol;Streptophenicol;Subital supp.;Suismycetin;Sulfaglobenicol;Sulfamycetin;Synthomycetina;Synthophtone;Tardomyocel;Tega-cetin;Tetrachlorasone;Tetracol;Tetranfen;Tetraphenicol;Tetra-phenicol oculos;Tiframilk;Tiromycetin;Toramin;Transicetina;Transpulmycin;Tribiotic;Trophen;Troymycetin;Tusolone;Tycloran;Uro-gliscal 500;Uroletten-s;Uroplex 4;Ut forte;Uvomycin;Variolan;V-crayolan;Vetical;Vetophenicol;Viceton;Viklorin;Virogin;Vitaklorin;Vsmpozim;Wintetil;Zoppib spray blu;Gotimycetin;Ichthoseptal;Iruxolum;Isicetina;Isopto fenicol;Kavipe;Kloramfex.

7.24 Therapeutic Function: Antimicrobial

7.25 World Health Organization (WHO): Chloramphenicol, an antibiotic isolated from Streptomyces venezuelae in 1947, first became available for general clinical use in 1948. By 1950 it was evident that its use could cause serious, sometimes fatal, blood dyscrasias. However, it remains one of the most effective antibiotics for treating invasive typhoid fever and salmonellosis, some rickettsioses and serious infections caused by Haemophilus influenzae or anaerobic organisms. This is considered to justify its retention in the WHO Model List of Essential Drugs. (Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert Committee, 722, , 1985)

7.26 Usage: Inhibitor of translation on the 50S subunit at the peptidyltransferase step. (R,R)-Chloramphenicol is widely utilized as an antibiotic, which is used for the treatment of number of bacterial infections and also act as a bacteriostatic. It is often used for bacterial selection in molecular biology applications. It also finds an application in ophthalmic and veterinary purposes. It also protects the mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

7.27 Antimicrobial activity: It is active against a very wide range of organisms. Minimum inhibitory concentrations (MICs) (mg/L) for other organisms are: Staphylococcus epidermidis, 1–8; Corynebacterium diphtheriae, 0.5–2; Bacillus anthracis, 1–4; Clostridium perfringens, 2–8; Mycobacterium tuberculosis, 8–32; Legionella pneumophila, 0.5–1; Bordetella pertussis, 0.25–4; Brucella abortus, 1–4; Campylobacter fetus, 2–4; Pasteurella spp., 0.25–4; Serratia marcescens, 2–8; Burkholderia pseudomallei, 4–8. Most Gramnegative bacilli are susceptible, but Pseudomonas aeruginosa is resistant. Leptospira spp., Treponema pallidum, chlamydiae, mycoplasmas and rickettsiae are all susceptible, but Nocardia spp. are resistant. It is widely active against anaerobes, including Actinomyces israelii (MIC 1–4 mg/L), Peptostreptococcus spp. (MIC 0.1–8 mg/L), and Fusobacterium spp. (MIC 0.5–2 mg/L), but Bacteroides fragilis is only moderately susceptible (MIC about 8 mg/L).
It is strictly bacteristatic against almost all bacterial species, but exerts a bactericidal effect at 2–4 times the MIC against some strains of Gram-positive cocci, Haemophilus influenzae and Neisseria spp. The minimum bactericidal concentrations (MBCs) for penicillin-resistant pneumococci are often significantly higher than those for penicillin- susceptible strains, although this cannot be detected by conventional disk susceptibility testing or MIC determination. Its bacteristatic effect may inhibit the action of penicillins and other β-lactam antibiotics against Klebsiella pneumoniae and other enterobacteria in vitro, but the clinical significance of this is doubtful. The presence of ampicillin does not affect the bactericidal effect of chloramphenicol on H. influenzae.

7.28 Acquired resistance: The prevalence of resistant strains in many Gram-positive and Gram-negative organisms reflects usage of the antibiotic. Over-the-counter sales are believed to have compounded the problem in some countries. For example, it has long been the drug of choice for the treatment of typhoid and paratyphoid fevers, but widespread use led to a high prevalence of resistant Salmonella enterica serotype Typhi. Outbreaks of infection caused by chloramphenicol-resistant S. Typhi have been seen since the early 1970s. Use of co-trimoxazole and fluoroquinolones in typhoid has resulted in a decline in chloramphenicol resistance in some endemic areas. Many hospital outbreaks caused by multiresistant strains of enterobacteria, notably Enterobacter, Klebsiella and Serratia spp., have been described.
Plasmid-borne resistance was first noted in shigellae in Japan and subsequently spread widely in Central America, where it was responsible for a huge outbreak. Strains of S. Typhi resistant to many antibiotics including chloramphenicol are particularly common in the Indian subcontinent. Resistance in shigellae is also relatively common in some parts of the world.
Resistant strains of H. influenzae (some also resistant to ampicillin), Staph. aureus and Streptococcus pyogenes are also encountered. Most N. meningitidis strains remain susceptible,but high-level resistance (MIC >64 mg/L) due to the production of chloramphenicol acetyltransferase has been described; the nucleotide sequence of the resistance gene was indistinguishable from that found on a transposon in Cl. perfringens. Resistant strains of Enterococcus faecalis are relatively common, and resistance to chloramphenicol is found in some multiresistant pneumococci.
Resistance in Staph. aureus is caused by an inducible acetyltransferase; additionally, the cfr (chloramphenicol– florfenicol resistance) gene encodes a 23S rRNA methyltransferase that also confers resistance to linezolid. In Escherichia coli, the capacity to acetylate chloramphenicol (at least three enzymes are involved) is carried by R factors. Replacement of the 3-OH group, which is the target of acetylation, accounts for the activity of fluorinated analogs against strains resistant to chloramphenicol and thiamphenicol. The resistance of B. fragilis and some strains of H. influenzae is also due to elaboration of a plasmid-encoded acetylating enzyme; in others it is due to reduced permeability resulting from loss of an outer membrane protein. Some resistant bacteria reduce the nitro group or hydrolyze the amide linkage. Resistance of Ps. aeruginosa is partly enzymic and partly due to impermeability.

7.29 General Description: Synthetic bacteriostatic antibiotic that inhibits the translation of RNA by blocking the peptidyltransferase reaction on ribosomes.

8. Computational chemical data

Molecular Weight: 323.12938g/mol
Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 322.0123269
Monoisotopic Mass: 322.0123269
Complexity: 342
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 115
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzOAAGAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgIUCAAADD/hmMYwwILQQgCJAiVSUwCCAAAgAgAoiIAIbIpKNiKAkZHEcABl1gGY2AeQ0KEOCAAAAAAAAAAQAAAAAAAAAAAAAAAAAA==

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