 |
Ampicillin
- Iupac Name：(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- CAS No.: 69-53-4
- Molecular Weight：349.40476
- Modify Date.: 2022-11-25 01:06
- Introduction: Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria.Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria.Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium.Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml.
View more+
1. Names and Identifiers
- 1.1 Name
- Ampicillin
- 1.2 Synonyms
(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid ab-pc amfipen ay-6108 binotal D-(&minus)-α-Aminobenzylpenicillin D(-)-ALPHA-AMINOBENZYLPENICILLIN D(-)-ALPHA-AMINOBENZYLPENICILLIN TRIHYDRATE D(-)-aplha-aminobenzylpenicillin EINECS 200-709-7 Marisilan MFCD00072036 p-50 Penstabil qidamp Rosampline Unasyn Wymox
- View all
- 1.3 CAS No.
- 69-53-4
- 1.4 CID
- 6249
- 1.5 EINECS(EC#)
- 200-709-7
- 1.6 Molecular Formula
- C16H19N3O4S (isomer)
- 1.7 Inchi
- InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
- 1.8 InChIkey
- AVKUERGKIZMTKX-NJBDSQKTSA-N
- 1.9 Canonical Smiles
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
- 1.10 Isomers Smiles
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
2. Properties
- 2.1 Density
- 1.45
- 2.1 Melting point
- 208℃
- 2.1 Boiling point
- 683.9℃ at 760 mmHg
- 2.1 Refractive index
- 1.6320 (estimate)
- 2.1 Flash Point
- 367.4℃
- 2.1 Precise Quality
- 349.11000
- 2.1 PSA
- 138.03000
- 2.1 logP
- 1.34720
- 2.1 Solubility
- NH4OH 1 M: 50?mg/mL, clear, colorless
- 2.2 Appearance
- Ampicillin trihydrate is an odorless white microcrystalline powder with a bitter taste. A 0.25% solution in water has a pH of 3.5 to 5.5. (NTP, 1992)
- 2.3 Storage
- Keep Cold.
- 2.4 Chemical Properties
- Crystalline Solid
- 2.5 Color/Form
- White, crystalline powder
White crystalline powder or as white, needle-like crystals
- 2.6 Contact Allergens
- Ampicillin caused contact dermatitis in a nurse alsosensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin)and in a pharmaceutical factoryworker. Systemic drug reactions are common. Crossreactivityis regular with ampicillin and can occur withother penicillins.
- 2.7 Odor
- Odorless or has a faint odor characteristic of the penicillins
- 2.8 pKa
- 2.5 (COOH)(at 25℃)
- 2.9 Water Solubility
- 13.9g/L(25 oC)
- 2.10 Spectral Properties
- Optical rotation = +287.9 deg at 20 deg C (C=1 in H2O)
- 2.11 Stability
- Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents.
- 2.12 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.
- 3.2 Potential Exposure
- Used as an antibiotic.
- 3.3 Shipping
- UN3077 Environmentally hazardous substances,solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardousmaterial, Technical Name Required.
- 3.4 Usage
- Ampicillin caused contact dermatitis in a nurse alsosensitized to amoxicillin (with tolerance to oralphenoxymethylpenicillin), and in a pharmaceuticalfactory worker.
- 3.5 Waste Disposal
- It is inappropriate and possiblydangerous to the environment to dispose of expired or wastepharmaceuticals by flushing them down the toiletor discarding them to the trash. Household quantities ofexpired or waste pharmaceuticals may be mixed with wet catlitter or coffee grounds, double-bagged in plastic, discard intrash. Larger quantities shall carefully take into considerationapplicable DEA, EPA, and FDA regulations. If possible returnthe pharmaceutical to the manufacturer for proper disposalbeing careful to properly label and securely package the material.Alternatively, the waste pharmaceutical shall be labeled,securely packaged and transported by a state licensed medicalwaste contractor to dispose by burial in a licensed hazardousor toxic waste landfill or incinerator. Ampicillin Preparation Products And Raw materials Raw materials
4. Safety and Handling
- 4.1 Symbol
- GHS07, GHS08
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- R36/37/38;R42/43
- 4.1 Safety Statements
- S22;S26;S36/37
- 4.1 Exposure Standards and Regulations
- Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
- 4.2 Packing Group
- I; II; III
- 4.2 Hazard Declaration
- H315-H317-H319-H334-H335
- 4.2 DisposalMethods
-
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.3 RIDADR
- OTH
- 4.3 Safety Profile
- Poison by intracerebral route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: fever, agranulocytosis, and other blood effects. An experimental teratogen. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NO, and SOx,.
- 4.4 Caution Statement
- P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311
- 4.4 Formulations/Preparations
- USP anhydrous ampicillin contains 900-1050 ug/mg ampicillin (calculated as the anhydrous base). Ampicillin is available in 125-, 200-, 250-, and 500-mg tablets that contain 90-120% labelled active ingredient, in 125-, 250-, and 500-mg capsules containing 90-120% labelled active ingredient, and as oral suspensions of 100, 125, and 250 mg/5 ml containing 90-120% of the labelled active ingredient and probenecid.
- 4.5 Incompatibilities
- May be incompatible with oxidizers(chlorates, nitrates, peroxides, permanganates, perchlorates,chlorine, bromine, fluorine, etc.); contact may cause firesor explosions. Keep away from alkaline materials, strongbases, strong acids, oxoacids, epoxides.
- 4.6 WGK Germany
- 2
- 4.6 RTECS
- XH8425000
- 4.6 Report
- EPA Genetic Toxicology Program. IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 (1990),p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210).
- 4.7 Safety
- Poison by intracerebral route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: fever, agranulocytosis, and other blood effects. An experimental teratogen. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Hazard Codes:Xn
Risk Statements: 36/37/38-42/43
S36/37/38:Irritating to eyes, respiratory system and skin.
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 22-26-36/37
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
- 4.8 Specification
- Ampicillin , its cas register number is 69-53-4. It also can be called D-(-)-alpha-Aminobenzylpenicillin ; Polyflex (Veterinary) ; and (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; D-(-)-alpha-Aminobenzylpenicillin .
- 4.9 Toxicity
- LD50 oral in mouse: > 5gm/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin sensitization, Category 1
Respiratory sensitization, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H317 May cause an allergic skin reaction H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| Precautionary statement(s) | |
| Prevention | P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P284 [In case of inadequate ventilation] wear respiratory protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/... |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
69-53-4Total: 3 Synthesis Route
8. Other Information
- 8.0 Merck
- 13,591
- 8.1 BRN
- 1090925
- 8.2 Brand Name(s)
- Human forms include Omnipen, Principen, Totacillin, Polycillin. Injectable forms include Omnipen-N, Polycillin-N, TotacillinN.
Veterinary forms include Amp-Equine, and Ampicillin trihydrate (Polyflex).
- 8.3 Description
- Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria.
Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria.
Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium.
Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml. - View all
- 8.4 Usage
- Ampicillin is used as asemi-synthetic antibiotic which has antibacterial activity structurally related to penicillin. It is widely used selection reagent for transformed cells expressing β-lactamase. It is also used to prevent and treat a number of bacterial infections. It may also be used to prevent group B streptococcal infection in newborns.
- 8.5 Chemical Properties
- Crystalline Solid
- 8.6 Chemical Properties
- Ampicillin in anhydrous form occurs as crystals.
- 8.7 Originator
- Binotal,Bayer,W. Germany,1962
- 8.8 Uses
- Ampicillin caused contact dermatitis in a nurse also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin), and in a pharmaceutical factory worker.
- 8.9 Uses
- β-lactam antibiotics
- 8.10 Uses
- Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.
- 8.11 Definition
- ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.
- 8.12 Manufacturing Process
- α-Carbobenzyloxyaminophenylacetic acid (0.1 mol), which is obtained by the reaction of equivalent quantities of α-aminophenylacetic acid and benzyl chlorocarbonate in aqueous sodium hydroxide, dissolved in dry acetone is stirred and cooled to approximately -5°C. To this there is added dropwise with continued cooling and stirring a solution of ethyl chlorocarbonate (0.1 mol). After approximately 10 minutes, the acylating mixture is cooled to about -5°C and then is slowly added to a stirred ice-cold mixture of 6-aminopenicillanic acid (0.1 mol), 3% sodium bicarbonate solution (0.1 mol) and acetone. This reaction mixture is allowed to attain room temperature, stirred for an additional thirty minutes at this temperature and then is extracted with ether.
The extracted aqueous solution is covered with butanol and the pH adjusted to 2 by the addition of HCl. The acidified aqueous phase is extracted with butanol, the pH of the aqueous phase being adjusted to pH 2 each time. The combined butanol solutions which contain the free acid, α- carbobenzyloxyaminobenzylpenicillin, are washed with water, and are then shaken with water to which sufficient 3% sodium bicarbonate has been added to bring the aqueous phase to pH 7. The process of washing and shaking is repeated with fresh water and bicarbonate solution. The combined aqueous solutions are washed with ether and then are evaporated under reduced pressure and low temperature. The product, the sodium salt of α- carbobenzyloxyaminobenzylpenicillin, is obtained as a yellow solid in a yield of 65%.
A suspension of palladium on barium carbonate (3.7 grams of 30%) in water (20 ml) is shaken in an atmosphere of hydrogen at room temperature. The catalyst is then filtered and washed well with water, care being taken that it does not become dry. A solution of the sodium salt of α- carbobenzyloxyaminobenzylpenicillin (4 grams) in water (20 ml) is added to the pretreated catalyst and the suspension is shaken in an atmosphere of hydrogen at room temperature and pressure for one hour. The catalyst is then filtered off, washed well with water, and the combined filtrate and washings adjusted to pH 7 with hydrochloric acid. The resulting solution is evaporated in vacuum at a temperature below 20°C to give α-aminobenzylpenicillin (2.4 grams, 74% yield), which is assayed at approximately 48% pure by the manometric method. - View all
- 8.13 Brand name
- Amcill (Parke-Davis); Omnipen (Wyeth-Ayerst); Polycillin (Apothecon); Principen (Apothecon).
- 8.14 Therapeutic Function
- Antibacterial
- 8.15 Contact allergens
- Ampicillin caused contact dermatitis in a nurse also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin) and in a pharmaceutical factory worker. Systemic drug reactions are common. Crossreactivity is regular with ampicillin and can occur with other penicillins.
- 8.16 Safety Profile
- Poison by intracerebral route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: fever, agranulocytosis, and other blood effects. An experimental teratogen. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NO, and SOx,.
- 8.17 Potential Exposure
- Used as an antibiotic.
- 8.18 Veterinary Drugs and Treatments
- In dogs and cats, ampicillin is not as well absorbed after oral administration as amoxicillin and its oral use has largely been supplanted by amoxicillin. It is used commonly in parenteral dosage forms when an aminopenicillin is indicated in all species.
The aminopenicillins, also called the “broad-spectrum” or ampicillin penicillins, have increased activity against many strains of gram-negative aerobes not covered by either the natural penicillins or penicillinase-resistant penicillins, including some strains of E. coli, Klebsiella, and Haemophilus.
- 8.19 Shipping
- UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
- 8.20 Incompatibilities
- May be incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
- 8.21 Waste Disposal
- It is inappropriate and possibly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. 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.
9. Computational chemical data
- Molecular Weight: 349.40476g/mol
- Molecular Formula: C16H19N3O4S
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 349.10962727
- Monoisotopic Mass: 349.10962727
- Complexity: 562
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 138
- Heavy Atom Count: 24
- Defined Atom Stereocenter Count: 4
- 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: AAADceB7OABAAAAAAAAAAAAAAABYAWAAAAAwAAAABYAAAAABAAAAHgQQCAAADCjF2ASyCIPAAgiIAiHSGACCAABgABAIiIGIBIgKYDqglTGUYABklgC4iAcYiICOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
Ampicillin is a broad-spectrum antibiotic belonging to the class of penicillin drugs. It works by inhibiting the synthesis of bacterial cell walls and can effectively combat various bacterial infectio..
-
Ampicillin mechanism of action is a captivating and essential aspect of understanding how this potent antibiotic combats bacterial infections. By inhibiting the synthesis of the bacterial cell wall, a..
-
Ampicillin, also known as ampicillin sodium, is a type of β-lactam antibiotic that is used to treat various bacterial infections. Properties Ampicillin is slightly soluble in water and insoluble in c..
-
Ampicillin is the most widely used oral penicillin antibiotic in veterinary clinical practice! By considering the physiological characteristics of animals, the characteristics of pathogenic microorgan..
11. Recommended Suppliers
-
- Products:Top quality and high purity with safe transportation and low price
- Tel:+86187-59294010-18759294010
- Email:Beata@xmwonderfulbio.com
Ampicillin
- Purity:99%Packing: 200kg/bag FOB
- Price: 120 USD/g
- Time: 2023/09/25
Inquire
-
- Products:We are engaged in the development, marketing and sales of apis, intermediates, natural products (extracts), fine chemicals, food additives, agricultural chemicals and other products.
- Tel:0086-0319-19133911216
- Email:Jany1001@chengcaibio.com
-
- Products:Pharmaceutical Intermediate , Apis , Food Additives , Herbal Extracts , Fine Chemicals , ...
- Tel:00-86-13167237119
- Email:anne@xljxcl.com
-
- Products:Cosmetic Raw Materials,solvents,etc.
- Tel:86-311-66562153
- Email:breeduan@crovellbio.com
-
- Products:My whatsapp:+86 13043111536 cas no.1451-82-7,79099-07-3,5449-12-7,5337-93-9,49851-31-2,288573-56-8
- Tel:86-311-13043116031
- Email:Fan@wh-xiju.com
12. Realated Product Infomation
skype
1YR
