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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
 

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

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/s1

InChIKey

AVKUERGKIZMTKX-NJBDSQKTSA-N

Smiles

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O

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.