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Substance Name: Cephapirin sodium [USAN:USP]
RN: 24356-60-3
UNII: 431LFF7I7J
InChIKey: VGEOUKPOQQEQSX-OALZAMAHSA-M

Note

  • Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms.

Molecular Formula

  • C17-H16-N3-Na-O6-S2

Molecular Weight

  • 445.4504
 

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Cephapirin sodium [USAN:USP]

Synonyms

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridylthio)acetyl)amino)-, monosodium salt, (6R-trans)-
  • 7-(alpha-(4-Pyridylthio)acetamido)cephalosporanic acid sodium salt
  • Ambrocef
  • Antibiotic BL-P 1322
  • BL-P 1322
  • BLP 1322
  • Brisfirina
  • Brisporin
  • Bristocef
  • Cefa lak
  • Cefa-Lak (Veterinary)
  • Cefadyl
  • Cefadyl IM/IV
  • Cefaloject
  • Cefapirin sodium
  • Cefapirina sodica
  • Cefatrex
  • Cefatrexyl
  • Cela-Lak/ToDay
  • Cephapirin sodium
  • Cephatrexil
  • Cephatrexyl
  • EINECS 246-194-2
  • Monosodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate acetate (ester)
  • NSC 179171
  • Sodium 7-(pyrid-4-ylthioacetamido)cephalosporanate
  • Sodium cefapirin
  • Sodium cephapirin
  • Today
  • UNII-431LFF7I7J

Systematic Names

  • 5-Thia-1-azabicyclo(4,2,0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester), monosodium salt
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridylthio)acetyl)amino)-, monosodium salt, (6R-trans)-
  • Sodium (6R-trans)-3-(acetoxymethyl)-8-oxo-7-((4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Registry Numbers

CAS Registry Number

  • 24356-60-3

FDA UNII

  • 431LFF7I7J

Related Registry Number

  • 21593-23-7 (Parent)

System Generated Number

  • 0024356603

Structure Descriptors

InChI

1S/C17H17N3O6S2.Na/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11;/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);/q;+1/p-1/t13-,16-;/m1./s1

InChIKey

VGEOUKPOQQEQSX-OALZAMAHSA-M

Smiles

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSc3ccncc3)SC1)C(=O)[O-].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2500mg/kg (2500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
man TDLo intramuscular 350mg/kg/6D (350mg/kg) BLOOD: AGRANULOCYTOSIS Antimicrobial Agents and Chemotherapy. Vol. 1, Pg. 174, 1972.
man TDLo intravenous 7429ug/kg/8W- (7.429mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 380, 1987.
mouse LD50 intraperitoneal 8899mg/kg (8899mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.
mouse LD50 intravenous 4600mg/kg (4600mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
mouse LD50 oral 26088mg/kg (26088mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.
mouse LD50 subcutaneous 13556mg/kg (13556mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.
rabbit LD50 intravenous 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
rat LD50 intraperitoneal 7850mg/kg (7850mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.
rat LD50 intravenous 4580mg/kg (4580mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 424, 1979.
rat LD50 oral 16356mg/kg (16356mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.
rat LD50 subcutaneous > 14400mg/kg (14400mg/kg)   Drugs in Japan Vol. 6, Pg. 405, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -5.030 (none)   EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.