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Home> Encyclopedia >   /  Antibiotic and antimicrobial agents  /  Pharmaceutical Intermediates  /  Pharmaceutical
Erythromycin structure
Erythromycin structure

Erythromycin

Iupac Name:(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
CAS No.: 114-07-8
Molecular Weight:733.937
Modify Date.: 2022-11-25 01:21
Introduction:

Erythromycin, an oral macrolide antibiotic produced by Streptomyces erythreus, reversibly binds to the 50S ribosome of bacteria, and inhibits protein synthesis.Target: AntibacterialErythromycin is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often prescribed for people who have an allergy to penicillins. For respiratory tract infections, it has better coverage of atypical organisms, including Mycoplasma and legione

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1. Names and Identifiers
1.1 Name
Erythromycin
1.2 Synonyms

(-)-ErythroMycin, Eur.Ph. (3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-Β-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2,10-dion (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name) abboticin abomacetin Ak-Mycin Aknemycin Aknin Dotycin E.E.S E-BASE EINECS 204-040-1 EMGEL EMU E-MYCIN Ergel Eritrocina eritromicina ERYC Erycen Erycin Erycinum Ery-Diolan Eryhexal ERYMAX Ery-Tab Erythrocin Erythrogran Erythroguent Erythromast 36 Erythromid Erythromycin A ErythroMycin COS/CGMP ERYTHROMYCIN THICYANATE erythromycine erythromycinum ERYTHROPED Estomicina ILOTYCIN Ilotycin, ErythroMycin Inderm knin MFCD00084654 Paediathrocin PCE Pharyngocin Retcin ROBIMYCIN Staticin Stiemycin StreptoMyces erythreus Theramycin Z Torlamicina UNII-63937KV33D USP

1.3 CAS No.
114-07-8
1.4 CID
12560
1.5 EINECS(EC#)
204-040-1; 245-407-6; 211-396-1
1.6 Molecular Formula
C37H67NO13 (isomer)
1.7 Inchi
InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
1.8 InChkey
ULGZDMOVFRHVEP-RWJQBGPGSA-N
1.9 Canonical Smiles
CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
1.10 Isomers Smiles
CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
2. Properties
3.1 Density
1.2
3.1 Melting point
138-140℃
3.1 Boiling point
818.4°Cat760mmHg
3.1 Refractive index
-74 ° (C=2, EtOH)
3.1 Flash Point
448.8°C
3.1 Precise Quality
733.46100
3.1 PSA
193.91000
3.1 logP
1.78560
3.1 Solubility
ethanol: soluble
3.2 AnalyticLaboratory Methods
Analyte: erythromycin;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards
3.3 Appearance
Fluffy colorless powder
3.4 Storage
Store at -20°C.
3.5 Chemical Properties
White to off white crystalline powder
3.6 Color/Form
Hydrated crystals from water
Crystals from water
White or slightly yellow crystals or powder
3.7 Decomposition
When heated to decomp it emits toxic fumes of /nitric oxides./
3.8 Odor
Odorless
3.9 PH
pH (saturated solution): 8 to 10.5; pH <4 is destructive
3.10 Physical
PHYSICAL DESCRIPTION: Fluffy colorless powder or fine white powder. (NTP, 1992)
3.11 pKa
8.8(at 25℃)
3.12 Water Solubility
soluble in water at 2mg/ml;ethanol: soluble
3.13 Spectral Properties
Specific optical rotation: -78 deg at 25 deg C/D (c = 1.99 in ethanol)
UV max absorption (pH 6.3): 280 nm (epsilon = 50)
Alcoholic solution is levorotatory
IR: 2:363G (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 3886 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
3.14 Stability
Stable under normal temperatures and pressures.
3.15 StorageTemp
Inert atmosphere,Room Temperature
3. Use and Manufacturing
4.1 General Description
Early in 1952, McGuire et al. reported the isolation oferythromycin (E-Mycin, Erythrocin, Ilotycin) fromStreptomyces erythraeus. It achieved rapid early acceptanceas a well-tolerated antibiotic of value for the treatment ofvarious upper respiratory and soft-tissue infections causedby Gram-positive bacteria. It is also effective against manyvenereal diseases, including gonorrhea and syphilis, andprovides a useful alternative for the treatment of many infectionsin patients allergic to penicillins. More recently,erythromycin was shown to be effective therapy for Eatonagent pneumonia (Mycoplasma pneumoniae), venereal diseasescaused by Chlamydia, bacterial enteritis caused byCampylobacter jejuni, and Legionnaires disease.The commercial product is erythromycin A, whichdiffers from its biosynthetic precursor, erythromycin B,in having a hydroxyl group at the 12-position of theaglycone. The chemical structure of erythromycin A was reportedby Wiley et al.197 in 1957 and its stereochemistry byCelmer198 in 1965. An elegant synthesis of erythronolide A,the aglycone present in erythromycin A, was described byCorey et al.The amino sugar attached through a glycosidic link to C-5 is desosamine, a structure found in several other macrolideantibiotics. The tertiary amine of desosamine (3,4,6-trideoxy-3-dimethylamino-D-xylo-hexose) confers a basiccharacter to erythromycin and provides the means by whichacid salts may be prepared. The other carbohydrate structurelinked as a glycoside to C-3 is called cladinose (2,3,6-trideoxy-3-methoxy-3-C-methyl-L-ribo-hexose) and isunique to the erythromycin molecule.
4.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 76 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 76 companies. For more detailed information, please visit ECHA C&L website

Of the 2 notification(s) provided by 75 of 76 companies with hazard statement code(s):

H317 (52%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (48%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H334 (52%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P321, P333+P313, P337+P313, P342+P311, P363, and P501
4.3 Methods of Manufacturing
Produced by fermentation of Streptomyces erythreus.?Obtained by butyl acetate extraction and cooling crystallization.
4.4 Purification Methods
It recrystallises from H2O to form hydrated crystals which melt at ca 135-140o, resolidifies and melts again at 190-193o. The melting point after drying at 56o/8mm is that of the anhydrous material and is at 137-140o. Its solubility in H2O is ~2mg/mL. The hydrochloride has m 170o, 173o (from aqueous EtOH, EtOH/Et2O). [Flynn et al. J Am Chem Soc 76 3121 1954, constitution: Wiley et al. J Am Chem Soc 79 6062 1957]. [Beilstein 18/10 V 398.]
4.5 Usage
Macrolide antibacterial
4. Safety and Handling
5.1 Hazard Codes
Xn
5.1 Risk Statements
R42/43
5.1 Safety Statements
S24;S37;S45
5.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including erythromycin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including erythromycin ethyl succinate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Erythromycin ethyl succinate/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including erythromycin lactobionate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Erythromycin lactobionate/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including erythromycin stearate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Erythromycin stearate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Erythromycin is included on this list.
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Erythromycin phosphate is included on this list. /Erythromycin phosphate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Erythromycin thiocyanate is included on this list. /Erythromycin thiocyanate/
Erythromycin. (1) Dog - For the treatment of bacterial pneumonia, upper respiratory infections (tonsillitis, bronchitis, tracheitis, pharyngitis, pleurisy), endometritis and metritis, and bacterial wound infections caused by Staphylococcus spp., Streptococcus spp., and Corynebacterium spp., sensitive to erythromycin. ... (2) Cats - For the treatment of bacterial pneumonia, upper respiratory infections (rhinitis, bronchitis), secondary infections associated with panleukopenia, and bacterial wound infections caused by Staphylococcus spp. and Streptococcus spp., susceptible to erythromycin. ... (3) Cattle - For the treatment of bovine respiratory disease (shipping fever complex and bacterial pneumonia) associated with Pasteurella multocida susceptible to erythromycin.
Erythromycin. Treatment of mastitis due to Staphylococcus aureus, Streptococcus agalactiae, Streptococcus dysgalactiae, and Streptococcus uberis in lactating or dry cows.
Tolerances for residues of erythromycin in food are established as follows: (a) 0.1 part per million in uncooked edible tissues of beef cattle and swine. (b) Zero in milk. (c) 0.025 part per million in uncooked eggs. (d) 0.125 part per million (negligible residue) in uncooked edible tissues of chickens and turkeys.
New animal drugs for use in animal feeds. Erythromycin thiocyanate. /Erythromycin thiocyanate/ Erythromycin thiocyanate in grams per ton Indications for use Limitations 4.6 to 18.5 Chickens; growth promotion and feed efficiency 9.25 to 18.5 Turkeys; growth promotion and feed efficiency For turkeys not over 12 weeks of age 9.25 to 64.75 Swine; increase in weight gain, improved feed efficiency in starter pigs (9.25 to 64.75) and grower-finishing pigs (9.25) Starter ration for animals up to 35 lb body weight 18.5 Laying chickens; aids in increasing egg production 92.5 1. Chickens; as an aid in the prevention of chronic respiratory disease during periods of stress Feed for 2 day before stress and 3 to 6 day after stress; withdraw 24 hours before slaughter 2. Chickens; as an aid in the prevention of infectious coryza Feed for 7 to 14 days; withdraw 24 hours before slaughter 3. Turkeys; as an aid in the prevention of chronic respiratory disease during periods of stress Feed for 2 days before stress and 3 to 6 days after stress 185 1. Chickens; as an aid in the prevention and reduction of lesions and in lowering severity of chronic respiratory disease Feed for 5 to 8 days; do not use in birds producing eggs for food purposes; withdraw 48 hours before slaughter 2. Turkeys; as an aid in the prevention and reduction of lesions and in lowering severity of chronic respiratory disease Feed for 5 to 8 days; do not use in birds producing eggs for food purposes
Erythromycin phosphate ... (1) Broiler and replacement chickens - As an aid in the control of chronic respiratory disease due to Mycoplasma gallisepticum susceptible to erythromycin. ... (2) Replacement chickens and chicken breeders - As an aid in the control of infectious coryza due to Hemophilus gallinarum susceptible to erythromycin. ... (3) Growing turkeys - As an aid in the control of blue comb (nonspecific infectious enteritis) caused by organisms susceptible to erythromycin. /Erythromycin phosphate/
5.2 Octanol/Water Partition Coefficient
log Kow = 3.06 [McFarland JW et al; J Med Chem 40: 1340-6 (1997)] PubMed Abstract
5.3 Other Preventative Measures
Airborne exposure should be controlled primarily by engineering controls such as general dilution ventilation, local exhaust ventilation, or process enclosure. Local exhaust ventilation is generally preferred to general exhaust because it can control the contaminant at its source, preventing dispersion into the work area. An industrial hygiene survey involving air monitoring may be sued to determine the effectiveness of engineering controls. Effectiveness of engineering controls intended for use with highly potent materials should be assessed by use of nontoxic surrogate materials.
As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mist, and/or vapors associated with this material. Clean equipment and work surfaces with suitable detergent or solvent after use. After removing gloves, wash hands and other exposed skin thoroughly.
For handling solutions, ensure that the glove material is protective against the solvent being used. Use handling practices that minimize direct hand contact. Employees who are sensitive to natural rubber (latex) should use nitrile or other synthetic nonlatex gloves. Use of powdered latex gloves should be avoided due to the risk of latex allergy.
Maintain eyewash facilities in the work area.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
5.4 Hazard Class
3
5.4 Cleanup Methods
Wear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage using a high-efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriate labeled container for disposal. Wash spill site.
5.5 DisposalMethods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful 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.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
5.6 RIDADR
MAC
5.6 Fire Fighting Procedures
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and material.
5.7 FirePotential
This material is assumed to be combustible.
5.8 Safety Profile
Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
5.9 Formulations/Preparations
Erythromycin Lactobionate Preparations Route of Administration Dosage Form Strength Brand of Generic Name (Manufacturer) Parenteral For injection, for IV infusion only 500 mg (of erythromycin) Erythromycin Lactobionate-IV (Abbott) Parenteral For injection, for IV infusion only 500 mg (of erythromycin) Erythromycin Lactobionate-IV ADD-Vantage (Abbott) Parenteral For injection, for IV infusion only 500 mg (of erythromycin) Erythromycin Piggyback (Abbott) Parenteral For injection, for IV infusion only 1 g (of erythromycin) Erythromycin Lactobionate-IV (Abbott) Parenteral For injection, for IV infusion only 1 g (of erythromycin) Erythromycin Lactobinate-IV Add-Vantage (Abbott)
Erythromycin Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Topical Gel 2% Erythromycin Gel (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Topical Gel 2% Erygel (Merz) Topical Ointment 2% Akne-Mycin (Healthpoint) Topical Solution 2% Erythromycin Solution (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Topical Solution 2% Erythra-Derm (Paddock)
Erythromycin Ethylsuccinate Preparations Route of Adminstration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral For suspension 100 mg (of erythromycin) per 2.5 mL EryPed Drops (Abbott) Oral For suspension 200 mg (of erythromycin) per 5 mL E.E.S. Granules (Abbott) Oral For suspension 200 mg (of erythromycin) per 5 mL EryPed (Abbott) Oral For suspension 400 mg (of erythromycin) per 5 mL EryPed (Abbott) Oral Suspension 200 mg (of erythromycin) per 5 mL E.E.S. Liquid (Abbott) Oral Suspension 200 mg (of erythromycin) per 5 mL Erythromycin Ethylsuccinate Suspension (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Suspension 400 mg (of erythromycin) per 5 mL E.E.S. Liquid (Abbott) Oral Suspension 400 mg (of erythromycin) per 5 mL Erythromycin Ethylsuccinate Suspension (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, chewable 200 mg (of erythromycin) EryPed, scored (Abbott) Oral Tablets, film-coated 400 mg (of erythromycin) E.E.S. Filmtab (Abbott) Oral Tablets, film-coated 400 mg (of erythromycin) Erythromycin Ethylsuccinate Film-coated Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
Erythromycin Stearate Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Tablets, film-coated 250 mg (of erythromycin) Erythrocin Stearate Filmtab (Abbott) Oral Tablets, film-coated 250 mg (of erythromycin) Erythromycin Stearate Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Tablets, film-coated 500 mg (of erythromycin) Erythrocin Stearate Filmtab (Abbott) Oral Tablets, film-coated 500 mg (of erythromycin) Erythromycin Stearate Tablets (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
Erythromycin Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Ophthalmic Ointment 0.5% Erythromycin Ophthalmic Ointment (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Ophthalmic Ointment 0.5% Romycin (OCuSOFT)
Erythromycin Estolate Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Capsules 250 mg (of erythromycin) Erythromycin Estolate Capsules (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Suspension 125 mg (of erythromycin) per 5 mL Erythromycin Estolate Suspension (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral Suspension 250 mg (of erythromycin) per 5 mL Erythromycin Estolate Suspension (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
5.10 WGK Germany
2
5.10 RTECS
KF4375000
5.10 Protective Equipment and Clothing
For handling of laboratory scale quantities, a cloth lab coat is recommended. Where significant quantities are handled, work clothing may be necessary to prevent take-home contamination.
Safety glasses with sideshields are recommended. Face shields or goggles may be required if splash potential exists or if corrosive materials are present. Approved eye protection (eg, bearing the ANSI Z87 OR CSA stamp) is preferred.
Where respirators are deemed necessary to reduce or control occupational exposures, use NIOSH-approved respiratory protection and have an effective respirator program in place.
5.11 Report

EPA Genetic Toxicology Program.

5.12 Skin, Eye, and Respiratory Irritations
Possible eye, skin, ... and/or respiratory tract irritation.
5.13 Safety

Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?HarmfulXn,IrritantXi
Risk Statements: 42/43-36/37/38?
R42/43:May cause sensitization by inhalation and skin contact.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 45-37-24-36-26?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S37:Wear suitable gloves.?
S24:Avoid contact with skin.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany: 2
RTECS of Erythromycin (CAS NO.114-07-8): KF4375000

5.14 Specification

? Erythromycin (CAS NO.114-07-8), its Synonyms are (3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione ; Abboticin ; Abomacetin ; Acneryne ; Acnesol ; Endoeritrin ; Erecin ; Erimycin-T . It is white to off white crystalline powder.

5.15 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 10mg/kg/1D-I (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Annals of Internal Medicine. Vol. 115, Pg. 69, 1991.
child TDLo oral 250mg/kg (250mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT
Pediatrics. Vol. 90, Pg. 624, 1992.
dog LDLo unreported > 100mg/kg (100mg/kg) ? Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
guinea pig LD50 intraperitoneal 413mg/kg (413mg/kg) ? Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
hamster LD50 oral 3018mg/kg (3018mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
mouse LD50 intramuscular 394mg/kg (394mg/kg) ? Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 44, Pg. 199, 1955.
mouse LD50 intraperitoneal 280mg/kg (280mg/kg) ? Journal of Antibiotics. Vol. 43, Pg. 938, 1990.
mouse LD50 intravenous 426mg/kg (426mg/kg) ? "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 273, 1967.
mouse LD50 oral 2580mg/kg (2580mg/kg) ? Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
mouse LD50 subcutaneous 1800mg/kg (1800mg/kg) ? Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
rat LD50 oral 4600mg/kg (4600mg/kg) ? Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
rat LDLo subcutaneous 427mg/kg (427mg/kg) ? Compilation of LD50 Values of New Drugs.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H319 Causes serious eye irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,3681
9.1 BRN
8183758
9.2 Description
Erythromycin ethyl succinate is a mixed double ester pro-drug in which one carboxyl of succinic acid esterifies the C-2′ hydroxyl of erythromycin and the other ethanol. This pro-drug frequently is used in an oral suspension for pediatric use largely to mask the bitter taste of the drug. Film-coated tablets also are used to deal with this. Some cholestatic jaundice is associated with the use of EES.
9.3 Description
Erythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains. It is active against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l). Erythromycin (10-40 mg/kg) dose-dependently inhibits the growth of S. aureus in a mouse model of thigh infection. It also inhibits the cytochrome P450 (CYP450) isoform CYP3A4 in vitro with IC50 values of 33 and 27.3 μM for α-hydroxytriazolam and 4-hydroxytriazolam formation, respectively, following administration of triazolam, which is known to be metabolized primarily by CYP3A4. Formulations containing erythromycin have been used in the treatment of bacterial respiratory and skin infections, pertussis, and a variety of other bacterial infections.
9.4 Chemical Properties
White to off white crystalline powder
9.5 Originator
Ilotycin,Dista,US,1952
9.6 Uses
Macrolide antibacterial
9.7 Uses
Erythromycin A is a 14-membered macrocyclic lactone with broad spectrum antibiotic activity, isolated from Saccharopolyspora erythraea (formerly Streptomyces erythreus) in 1952. Erythromycin is one of only a handful of microbial metabolites to have profoundly shaped the treatment of bacterial disease in the last 50 years. Erythromycin has given rise to new generations of semi-synthetic derivatives with improved stability and potency. Our product has been HPLC-purified to remove contaminants and degradation products.
9.8 Uses
For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections
9.9 Uses
Labeled Erythromycin, intended for use as an internal standard for the quantification of Erythromycin by GC- or LC-mass spectrometry.
9.10 Definition
An antibiotic produced by growth of Streptomyces erythreus Waksman. It is effective against infections caused by Gram-positive bacteria, including some β-hemolytic streptococci, pneumococci, and staphylococci.
9.11 Indications
Erythromycin is an antibiotic in the macrolide family that also has promotility effects because it is a motilin agonist.
9.12 Manufacturing Process
An inoculum broth is prepared having the following composition: 32 pounds starch; 32 pounds soybean meal; 10 pounds corn steep solids; 10 pounds sodium chloride; 6 pounds calcium carbonate; and 250 gallons water.
The broth is placed in an iron tank of 350 gallon capacity and is sterilized by heating it under pressure at a temperature of about 120°C for 30 minutes. The sterilized broth is cooled and inoculated aseptically with spores of Streptomyces erythreus, NRRL 2338. The organism is grown in the broth at about 26°C for a period of 45 hours. During the growth period the broth isstirred and aerated with sterile air in the amount of about 0.5 volume of air per volume of culture broth per minute.
In a 1,600-gallon iron tank is placed a fermentation broth having the following composition: 153 pounds starch; 153 pounds soybean meal; 51 pounds corn steep solids; 33 pounds calcium carbonate; 51 pounds sodium chloride; and 1,200 gallons water.
The culture broth is sterilized by heating it under pressure at about 120°C for about 30 minutes. The broth is cooled and the above inoculant culture is added aseptically. The organism is grown in the broth for 4 days at a temperature of 26°C. During the growth period the broth is stirred and sterile air is blown through the broth at a rate of about 0.5 volume of air per volume of broth per minute. At the end of the growth period the broth shows an antibiotic activity equivalent to about 150 mcg of erythromycin per ml of broth.
The culture broth (about 1,100 gallons in volume) is adjusted to pH 9.5 with 40% sodium hydroxide solution and is filtered to remove the mycelium, the filtration being assisted by use of 3% of Hyflo Super-Cel, a filter aid, (sold by Johns-Manville Company). The clear filtrate is extracted with amyl acetate in a Podbielniak extractor using a ratio of 1 volume of amyl acetate to 6 volumes of clarified broth. The amyl acetate extract is in turn extracted batchwise with water brought to about pH 5 by the addition of sulfuric acid. Two extractions are carried out, the first with ? volume and the second with ? volume of water adjusted to pH 5 with sulfuric acid. The aqueous extracts are combined and adjusted to pH 8.0 with sodium hydroxide solution.
The alkaline solution is concentrated in vacuo to a volume of about 30 gallons and the solution is then adjusted to pH 9.5 by the addition of aqueous sodium hydroxide and is allowed to stand. Erythromycin separates as a crystalline material. The crystals are filtered off, the mother liquor is adjusted to about pH 8 by the addition of dilute sulfuric acid and is concentrated in vacuo to a volume of about 30 gallons. The solution is adjusted to about pH 9.5 and allowed to stand, whereupon an additional amount of erythromycin separates in crystalline form. The total amount of erythromycin obtained is about 256 grams. The erythromycin is purified by several recrystallizations from aqueous acetone (2:1 mixture), according to US Patent 2,653,899.
9.13 Brand name
Ilotycin (Dista).
9.14 Therapeutic Function
Antibacterial
9.15 Antimicrobial activity
Gram-positive rods, including Clostridium spp. (MIC50 0.1–1 mg/L), C. diphtheriae (MIC50 0.1–1 mg/L), L. monocytogenes (MIC50 0.1–0.3 mg/L) and Bacillus anthracis (MIC50 0.5–1.0 mg/L), are generally susceptible. Most strains of M. scrofulaceum and M. kansasii are susceptible (MIC50 0.5–2 mg/L), but M. intracellulare is often and M. fortuitum regularly resistant. Nocardia isolates are resistant. H. ducreyi, B. pertussis (MIC50 0.03–0.25 mg/L), some Brucella, Flavobacterium, Legionella (MIC50 0.1–0.5 mg/L) and Pasteurella spp. are susceptible. H. pylori (MIC 0.06–0.25 mg/L) and C. jejuni are usually susceptible, but C. coli may be resistant. Most anaerobic bacteria, including Actinomyces and Arachnia spp., are susceptible or moderately so, but B. fragilis and Fusobacterium spp. are resistant. T. pallidum and Borrelia spp. are susceptible, as are Chlamydia spp. (MIC ≤0.25 mg/L), M. pneumoniae and Rickettsia spp. M. hominis and Ureaplasma spp. are resistant.
Enterobacteriaceae are usually resistant. Activity rises with increasing pH up to 8.5. Incubation in 5–6% CO2 raises the MIC for H. influenzae from 0.5–8 to 4–32 mg/L; MICs for Str. pneumoniae and Str. pyogenes also rise steeply. Activity is predominantly bacteristatic.
9.16 Acquired resistance
In Europe, the USA and other countries the incidence of resistance in Str. pneumoniae ranges from 5% to over 60%. In Str. pneumoniae strains resistant or intermediately susceptible to penicillin G, resistance rates above 80% have been reported. Increasing rates of resistance in clinical isolates of Str. pyogenes have also been reported, threatening its use as an alternative to penicillin G in allergic patients.
Lower rates of resistance have been reported in other bacterial species, including methicillin-resistant Staph. aureus, coagulase-negative staphylococci, Str. agalactiae, Lancefield group C and G streptococci, viridans group streptococci, H. pylori, T. pallidum, C. diphtheriae and N. gonorrhoeae.
9.17 General Description
Early in 1952, McGuire et al. reported the isolation oferythromycin (E-Mycin, Erythrocin, Ilotycin) fromStreptomyces erythraeus. It achieved rapid early acceptanceas a well-tolerated antibiotic of value for the treatment ofvarious upper respiratory and soft-tissue infections causedby Gram-positive bacteria. It is also effective against manyvenereal diseases, including gonorrhea and syphilis, andprovides a useful alternative for the treatment of many infectionsin patients allergic to penicillins. More recently,erythromycin was shown to be effective therapy for Eatonagent pneumonia (Mycoplasma pneumoniae), venereal diseasescaused by Chlamydia, bacterial enteritis caused byCampylobacter jejuni, and Legionnaires disease.
The commercial product is erythromycin A, whichdiffers from its biosynthetic precursor, erythromycin B,in having a hydroxyl group at the 12-position of theaglycone. The chemical structure of erythromycin A was reportedby Wiley et al.197 in 1957 and its stereochemistry byCelmer198 in 1965. An elegant synthesis of erythronolide A,the aglycone present in erythromycin A, was described byCorey et al.
The amino sugar attached through a glycosidic link to C-5 is desosamine, a structure found in several other macrolideantibiotics. The tertiary amine of desosamine (3,4,6-trideoxy-3-dimethylamino-D-xylo-hexose) confers a basiccharacter to erythromycin and provides the means by whichacid salts may be prepared. The other carbohydrate structurelinked as a glycoside to C-3 is called cladinose (2,3,6-trideoxy-3-methoxy-3-C-methyl-L-ribo-hexose) and isunique to the erythromycin molecule.
9.18 Pharmaceutical Applications
A natural antibiotic produced as a complex of six components (A–F) by Saccharopolyspora erythraea. Only erythromycin A has been developed for clinical use. It is available in a large number of forms for oral administration: the base compound (enteric- or film-coated to prevent destruction by gastric acidity); 2′-propionate and 2′-ethylsuccinate esters; a stearate salt; estolate and acistrate salts of 2′-esters. The 2′-esters and their salts have improved pharmacokinetic and pharmaceutical properties and are less bitter than erythromycin. It is also formulated as the lactobionate and gluceptate forparenteral use.
9.19 Biological Activity
Erythromycin is the principal one in antimicrobial drugs. Although available as the parent entity, semisynthetic derivatives have proved to be clinically superior to the natural cogener. Like the tetracyclines, synthetic transformations in the macrolide series have not significantly altered their antibacterial spectra, but have improved the pharmacodynamic properties. For example, the propionate ester of erythromycin lauryl sulfate (erythromycin estolate) has shown greater acid stability than the unesterified parent substance. Although the estolate appears in the blood somewhat more slowly, the peak serum levels reached are higher and persist longer than other forms of the drug. However, cholestatic hepatitis may occasionally follow administration of the estolate and, for that reason, the stearate is often preferred. Erythromycin is effective against Group A and other nonenterococcal streptococci, Corynebacterium diphtheriae, Legionella pneumophila, Chlamydia trachomatis, Mycoplasma pneumoniae, and Flavobacterium. Because of the extensive use of erythromycin in hospitals, a number of Staph. aureus strains have become highly resistant to the drug. For this reason, erythromycin has been used in combination with chloramphenicol. This combination is also used in the treatment of severe sepsis when etiology is unknown and patient is allergic to penicillin.
9.20 Biochem/physiol Actions
Mode of Action: Erythromycin acts by inhibiting elongation at the transpeptidation step, specifically aminoacyl translocation from the A-site to P-site by binding to the 50s subunit of the bacterial 70s rRNA complex.Antimicrobial Spectrum: This product acts against both gram-negative and gram-positive bacteria.
9.21 Pharmacology
Erythromycin inhibits bacterial protein synthesis by reversibly binding with their 50 S ribosomal subunit, thus blocking the formation of new peptide bonds. Erythromycin is classified as a bacteriostatic antibiotic.
However, it can also exhibit a bactericidal effect against a few types of microbes at certain concentrations.
Bacterial resistance to erythromycin can originate by two possible mechanisms: the inability of reaching the cell membrane, which is particularly relevant in the case of the microorganisms Enterobacteriaceae, or in the case of the presence of a methylated alanine in the 23 S ribosomal RNA of the 50 S subunit, which lowers the affinity of erythromycin to it. Erythromycin acts on Gram-positive (staphylococci both produced and not produced by penicillinase, streptococci, pneumococci, clostridia) and a few Gram-negative microorganisms (gonococci, brucelli, hemophile and whooping cough bacilli, legionelli), mycoplasma, chlamydia, spirochaeta, and Rickettsia. Colon and blue-pus bacilli, as well as the bacilli shigella, salmonella, and others are resistant to erythromycin.
9.22 Pharmacokinetics
absorption and metabolism
The acid lability of erythromycin base necessitates administration in a form giving protection from gastric acid. In acid media it is rapidly degraded (10% loss of activity at pH 2 in less than 4 s) by intramolecular dehydrogenation to a hemiketal and hence to anhydroerythromycin A, neither of which exerts antibacterial activity. Delayed and incomplete absorption is obtained from coated tablets and there is important inter- and intra-individual variation, adequate levels not being attained at all in a few subjects. Food delays absorption of erythromycin base. After 500 mg of the 2′-ethylsuccinyl ester, mean peak plasma levels at 1–2 h were 1.5 mg/L. In subjects given 1 g of the 2′-ethylsuccinate every 12 h for seven doses, the mean plasma concentration 1 h after the last dose was around 1.4 mg/L. Intra- and inter-subject variation and delayed and erratic absorption in the presence of food have not yet been eliminated by new formulations. Improved 500 mg preparations of erythromycin stearate are claimed to produce peak plasma levels of 0.9–2.4 mg/L that are little affected by the presence of food. 2′-Esters of erythromycin are partially hydrolyzed to erythromycin: 2′-acetyl erythromycin is hydrolyzed more rapidly than the 2′-propionyl ester, but more slowly than the 2′-ethylsuccinate.
The stoichiometric mixture with stearate does not adequately protect erythromycin from acid degradation. After an oral dose of erythromycin stearate, equivalent concentrations of erythromycin and its main degradation product, anhydroerythromycin, could be detected.
Doses of 10 mg/kg produced mean peak plasma concentrations around 1.8 mg/L in infants weighing 1.5–2 kg and 1.2 mg/L in those weighing 2–2.5 kg. In infants less than 4 months old, doses of 10 mg/kg of the 2′-ethylsuccinate every 6 h produced steady state plasma levels of around 1.3 mg/L. The apparent elimination half-life was 2.5 h. In children given 12.5 mg/kg of erythromycin 2′-ethylsuccinate every 6 h, the concentration in the plasma 2 h after the fourth dose was around 0.5–2.5 mg/L.
Distribution
Very low levels are obtained in cerebrospinal fluid (CSF), even in the presence of meningeal inflammation, and after parenteral administration. Levels of 0.1 mg/L in aqueous humor were found when the serum level was 0.36 mg/L, but there was no penetration into the vitreous. In children with otitis media given 12.5 mg/kg of erythromycin 2′- ethylsuccinate every 6 h, concentrations in middle ear exudate were 0.25–1 mg/L. In patients with chronic serous otitis media given 12.5 mg/kg up to a maximum of the equivalent of 500 mg, none was detected in middle ear fluid, but on continued treatment levels up to 1.2 mg/L have been described.
Penetration also occurs into peritoneal and pleural exudates. Mean concentrations of 2.6 mg/L have been found in sputum in patients receiving 1 g of erythromycin lactobionate intravenously every 12 h and 0.2–2 mg/L in those receiving an oral stearate formulation. Levels in prostatic fluid are about 40% of those in the plasma. Salivary levels of around 4 mg/L were found in subjects receiving doses of 0.5 g every 8 h at 5 h after a dose, when the plasma concentration was around 5.5 mg/L. Intracellular:extracellular ratios of 4–18 have been found in polymorphonuclear neutrophils.
Fetal tissue levels are considerably higher after multiple doses: when the mean peak maternal serum level was 4.94 (0.66–8) mg/L, the mean fetal blood concentration was 0.06 (0–0.12) mg/L. Concentrations were more than 0.3 mg/L in amniotic fluid and most other fetal tissues, but the concentrations were variable and unmeasurable in some. Erythromycin appears to be concentrated by fetal liver.
excretion
Erythromycin is excreted both in urine and in the bile but only a fraction of the dose can be accounted for in this way. Only about 2.5% of an oral dose or 15% of an intravenous dose is recovered unchanged in the urine. It is not removed to any significant extent by peritoneal dialysis or hemodialysis. Reported changes in apparent elimination half-life in renal impairment may be related to the saturable nature of protein binding. Fairly high concentrations (50–250 mg/L) are found in the bile. In cirrhotic patients receiving 500 mg of the base, peak plasma levels were higher and earlier than in healthy volunteers (2.0 and 1.5 mg/L at 4.6 and 6.3 h, respectively). The apparent elimination half-life was 6.6 h. It is possible that the smaller excretion of the 2′-propionyl ester in the bile in comparison to the base accounts in part for its better-maintained serum levels. There is some enterohepatic recycling, but some of the administered dose is lost in the feces, producing concentrations of around 0.5 mg/g.
9.23 Usage
Erythromycin, is used as a macrolide antibiotic protein synthesis inhibitor. It is widely used in cell culture applications. Depending upon the strain of bacteria, erythromycin has been used between 50 and 200 mg/L to control bacterial growth. Erythromycin resistance can be induced in bacteria.
9.24 Clinical Use
Erythromycin is used (offlabel indication) to accelerate gastric emptying in diabetic gastroparesis and postoperative gastroparesis. Tachyphylaxis will occur, so it cannot be used uninterruptedly for long periods.
9.25 Side effects
Oral administration, especially of large doses, commonly causes epigastric distress, nausea and vomiting, which may be severe. Solutions are very irritant: intravenous infusions almost invariably produce thrombophlebitis. Cholestatic hepatitis occurs rarely. Transient auditory disturbances have been described after intravenous administration of the lactobionate salt, and occasionally in patients with renal and hepatic impairment in whom oral dosage has produced high plasma levels. Sensorineural hearing impairment can occur and, although this is usually a reversible effect which occurs at high dosage, can be permanent. Prolongation of the apparent elimination half-life of carbamazepine, due to inhibition of its conversion to the epoxide, usually results in central nervous system (CNS) disturbances. Nightmares are troublesome in some patients. Allergic effects occur in about 0.5% of patients.
The estolate is particularly prone to give rise to liver abnormalities, consisting of upper abdominal pain, fever, hepatic enlargement, a raised serum bilirubin, pale stools and dark urine and eosinophilia. The condition is rare and usually seen 10–20 days after the initiation of treatment, with complete recovery on stopping the drug. Recurrence of symptoms can be induced by giving the estolate but not the base or stearate. There is evidence that erythromycin estolate is more toxic to isolated liver cells than is the 2′-propionate or the base, and it is suggested that the essential molecular feature responsible for toxicity is the propionyl–ester linkage. The relative frequency of the reaction, its rapidity of onset (within hours) after second courses of the drug, evidence of hypersensitivity and the histological appearance suggest a mixture of hepatic cholestasis, liver cell necrosis and hypersensitivity. Abnormal liver function tests in patients receiving the estolate must be interpreted with caution, since increased levels of transaminases is often the only abnormality and some metabolites of the estolate can interfere with the measurement commonly used. Elevated levels of transaminases return to normal after cessation of treatment. Serum bilirubin is generally unchanged in these patients, but γ-glutamyl transpeptidase may also be affected.
9.26 Safety Profile
Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
9.27 Chemical Synthesis
Erythromycin, (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2,6-dideoxy-3-Cmethyl-3-O-methyl-α-L-ribo-hexopyranosyl)-oxy]-14-ethyl-7,12,13-trihydroxy- 3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy ]oxacyclotetradecan-2,10-dione (32.2.1), is more specifically called erythromycin A. It was first isolated in 1952 from the culture liquid of microorganisms of the type Streptomyces erytherus. Minor amounts of erythromycin B and C were also found in the culture fluid. Erythromycin B differs from A in that a hydrogen atom is located at position 12 in the place of a hydroxyl group, while erythromycin C differs from A in that the residue of a different carbohydrate, micarose (2-6-di-deoxy-3-C-methyl-L-ribohexose), is bound to the macrocycle in position 3 in the place of cladinose (4-methoxy-2,4-dimethyl-tetrahydropyran-3,6-diol).
Erythromycin A is produced only microbiologically using active strains of microorganisms of the type Saccharopolospora erythraea.

9.28 Veterinary Drugs and Treatments
Erythromycin is approved for use to treat infections caused by susceptible organisms in swine, sheep, and cattle. It is often employed when an animal is hypersensitive to penicillins or if other antibiotics are ineffective against a certain organism.
Erythromycin, at present, is considered to be one of the treatments of choice (with rifampin) for the treatment of C. (Rhodococcus) equi infections in foals. Erythromycin estolate and microencapsulated base appear to be the most efficacious forms of the drug in foals due to better absorption and less frequent adverse effects.
Erythromycin may be used as a prokinetic agent to increase gastric emptying in dogs and cats. It may also be beneficial in treating reflux esophagitis.
9.29 Purification Methods
It recrystallises from H2O to form hydrated crystals which melt at ca 135-140o, resolidifies and melts again at 190-193o. The melting point after drying at 56o/8mm is that of the anhydrous material and is at 137-140o. Its solubility in H2O is ~2mg/mL. The hydrochloride has m 170o, 173o (from aqueous EtOH, EtOH/Et2O). [Flynn et al. J Am Chem Soc 76 3121 1954, constitution: Wiley et al. J Am Chem Soc 79 6062 1957]. [Beilstein 18/10 V 398.]
9.30 Dosage forms
1 g/day in divided doses.
9.31 Storage Conditions
Produced by fermentation of Streptomyces erythreus.?Obtained by butyl acetate extraction and cooling crystallization.
10. Computational chemical data
  • Molecular Weight: 733.937g/mol
  • Molecular Formula: C37H67NO13
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 733.46124119
  • Monoisotopic Mass: 733.46124119
  • Complexity: 1180
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 14
  • Topological Polar Surface Area: 194
  • Heavy Atom Count: 51
  • Defined Atom Stereocenter Count: 18
  • 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: AAADcfB+PAAAAAAAAAAAAAAAAAAAAAAAAAAkSAAAAAAAAAAAAAAAHgAACAAADXzxgAcCCAMABgAIAICQCAAAAAAAAAAAAAEIAAATEBYAgAAmQAAHIAAXAAHK7PzOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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