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Substance Name: Ampicillin sodium [USAN:USP:JAN]
RN: 69-52-3
UNII: JFN36L5S8K
InChIKey: KLOHDWPABZXLGI-YWUHCJSESA-M

Note

  • Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.

Molecular Formula

  • C16-H19-N3-O4-S.Na

Molecular Weight

  • 371.3912
 

Classification Codes

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 2A
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Names and Synonyms

Name of Substance

  • Ampicillin sodium [USAN:USP:JAN]

Synonyms

  • Alpen-N
  • Amcill-S
  • Ampicillin natrium
  • Ampicillin sodium
  • Ampicillin sodium salt
  • Binotal sodium
  • Citteral
  • D(-)-alpha-Aminobenzylpenicillin sodium salt
  • Domicillin
  • EINECS 200-708-1
  • Monosodium (2S,5R,6R)-6-((R)-2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
  • Monosodium D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
  • Omnipen
  • Omnipen-N
  • PEN A/N
  • Penbritin
  • Penbritin-S
  • Penialmen
  • Pentrexyl
  • Polycillin
  • Polycillin-N
  • Principen
  • Principen/N
  • Sodium ampicillin
  • Sodium binotal
  • Sodium D-(-)-alpha-aminobenzylpenicillin
  • Sodium P-50
  • Totacillin
  • Totacillin-N
  • UNII-JFN36L5S8K

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (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-, sodium salt, D-(-)-
  • Sodium (2S-(2alpha,5alpha,6beta(S*)))-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

Superlist Name

  • Ampicillin sodium

Mixture Name

  • Unasyn

Registry Numbers

CAS Registry Number

  • 69-52-3

FDA UNII

  • JFN36L5S8K

Related Registry Number

  • 69-53-4 (Parent)

System Generated Number

  • 0000069523

Molecular Formulas

Molecular Formula

  • C16-H19-N3-O4-S.Na

Molecular Formula Fragments

  • C16-H19-N3-O4-S
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C16H19N3O4S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1

InChIKey

KLOHDWPABZXLGI-YWUHCJSESA-M

Smiles

N(C(=O)[C@@H](c1ccccc1)N)[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 5700mg/kg (5700mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 oral > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
mouse LD50 subcutaneous > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
mouse LDLo intravenous 2657mg/kg (2657mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
rat LD50 intraperitoneal 7400mg/kg (7400mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 oral > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
rat LD50 subcutaneous > 5314mg/kg (5314mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 18, Pg. 356, 1962.
women TDLo oral 100mg/kg/5D (100mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES
Lancet. Vol. 2, Pg. 707, 1978.