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Substance Name: Ampicillin [USAN:USP:INN:BAN:JAN]
RN: 69-53-4
UNII: 7C782967RD
InChIKey: AVKUERGKIZMTKX-NJBDSQKTSA-N
Note
- Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Molecular Formula
- C16-H19-N3-O4-S
Molecular Weight
- 349.4091
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterial
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Reproductive Effect
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 2A
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Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
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Names and Synonyms
Name of Substance
- Ampicillin
- Ampicillin [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Ampicillin
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
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-
- 6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid
- 6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
- AB-PC
- AB-PC Sol
- Acillin
- Adobacillin
- Alpen
- Amblosin
- Amcill
- Amfipen
- Amfipen V
- Aminobenzylpenicillin
- Amipenix S
- Ampi-bol
- Ampi-Co
- Ampi-Tab
- Ampichel
- Ampicil
- Ampicilina
- Ampicilina [INN-Spanish]
- Ampicillin
- Ampicillin A
- Ampicillin acid
- Ampicillin anhydrate
- Ampicillina
- Ampicillina [DCIT]
- Ampicilline
- Ampicilline [INN-French]
- Ampicillinum
- Ampicillinum [INN-Latin]
- Ampicin
- Ampifarm
- Ampikel
- Ampimed
- Ampipenin
- Ampiscel
- Ampisyn
- Ampivax
- Ampivet
- Amplacilina
- Amplin
- Amplipenyl
- Amplisom
- Amplital
- Ampy-Penyl
- Austrapen
- AY 6108
- AY-6108
- BA 7305
- Bayer 5427
- Binotal
- Bonapicillin
- Britacil
- BRL 1341
- BRL-1341
- Campicillin
- Cimex
- Copharcilin
- D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid
- D-(-)-alpha-Aminobenzylpenicillin
- D-(-)-alpha-Aminopenicillin
- D-(-)-Ampicillin
- D-Ampicillin
- D-Cillin
- Delcillin
- Deripen
- Divercillin
- Doktacillin
- Duphacillin
- EC 200-709-7
- EINECS 200-709-7
- Grampenil
- Guicitrina
- HI 63
- HSDB 3009
- Lifeampil
- Morepen
- Norobrittin
- Novo-ampicillin
- NSC 528986
- NSC-528986
- Nuvapen
- Olin Kid
- Omnipen
- Orbicilina
- P 50
- P-50
- Pen A
- Pen Ampil
- Penbristol
- Penbritin
- Penbritin paediatric
- Penbritin syrup
- Penbrock
- Penicillin, (aminophenylmethyl)-
- Penicline
- Penimic
- Pensyn
- Pentrex
- Pentrexl
- Pentrexyl
- Pfizerpen A
- Polycillin
- Ponecil
- Princillin
- Principen
- Qidamp
- Racenacillin
- Ro-Ampen
- Rosampline
- Roscillin
- Semicillin
- Semicillin R
- Servicillin
- SK-Ampicillin
- SQ 17382
- Sumipanto
- Supen
- Synpenin
- Texcillin
- Tokiocillin
- Tolomol
- Totacillin
- Totalciclina
- Totapen
- Trifacilina
- Ultrabion
- Ultrabron
- UNII-7C782967RD
- Vampen
- Viccillin
- Viccillin S
- WY-5103
- Wypicil
Systematic Names
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)-
- Ampicillin
Superlist Name
- Ampicillin
Mixture Name
- Polyflex (Veterinary)
Registry Numbers
CAS Registry Number
- 69-53-4
FDA UNII
- 7C782967RD
Other Registry Numbers
- 33604-21-6
- 37234-64-3
- 47355-94-2
- 50584-05-9
- 800-79-3
- 8056-87-9
- 96707-69-6
- 98520-55-9
Related Registry Numbers
- 69-52-3 (mono-hydrochloride salt)
- 7177-48-2 (trihydrate)
System Generated Number
- 0000069534
Structure Descriptors
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/s1InChIKey
AVKUERGKIZMTKX-NJBDSQKTSA-NSmiles
CC1(C)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | > 100mg/kg (100mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
guinea pig | LD50 | unreported | 7500ug/kg (7.5mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
man | TDLo | oral | 400mg/kg/4W-I (400mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: OTHER CHANGES | Annals of Internal Medicine. Vol. 69, Pg. 91, 1968. |
mouse | LD50 | intracrebral | 380mg/kg (380mg/kg) | BEHAVIORAL: EXCITEMENT MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Chemotherapy Vol. 26, Pg. 196, 1980. |
mouse | LD50 | intraperitoneal | 3250mg/kg (3250mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 83, 1980. |
mouse | LD50 | intravenous | 4600mg/kg (4600mg/kg) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 987, 1977. | |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 57, 1982. | |
mouse | LD50 | parenteral | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. -, Pg. 114, 1995. | |
mouse | LD50 | unreported | 28gm/kg (28000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
mouse | LDLo | subcutaneous | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
rat | LD50 | intraperitoneal | 4500mg/kg (4500mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
rat | LD50 | intravenous | 6200mg/kg (6200mg/kg) | Drugs in Japan Vol. -, Pg. 88, 1990. | |
rat | LD50 | parenteral | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. -, Pg. 114, 1995. | |
rat | LD50 | unreported | 10gm/kg (10000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977. | |
rat | LDLo | oral | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
rat | LDLo | subcutaneous | > 5gm/kg (5000mg/kg) | British Medical Journal. Vol. 2, Pg. 197, 1961. | |
women | TDLo | oral | 160mg/kg/4D-I (160mg/kg) | BLOOD: THROMBOCYTOPENIA BLOOD: AGRANULOCYTOSIS | Annals of Internal Medicine. Vol. 99, Pg. 573, 1983. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 208 dec | deg C | EXP | |
log P (octanol-water) | 1.35 | (none) | EXP | |
Water Solubility | 1.01E+04 | mg/L | 21 | EXP |
Vapor Pressure | 7.75E-15 | mm Hg | 25 | EST |
Henry's Law Constant | 2.39E-17 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.03E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.