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Substance Name: Cefapirin [INN:BAN]
RN: 21593-23-7
UNII: 89B59H32VN
InChIKey: UQLLWWBDSUHNEB-CZUORRHYSA-N

Note

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

Molecular Formula

  • C17-H17-N3-O6-S2

Molecular Weight

  • 423.468
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Cefapirin [INN:BAN]
  • Cephapirin

MeSH Heading

  • Cephapirin

Synonyms

  • (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
  • 3-(Hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamidol-5-thia-1-azabicyclo(4.2.0)oct-2-en-2carbonsaeure acetat
  • 7-(2-(4-Pyridylthio)acetamido)cephalosporanic acid
  • BRN 1095157
  • Cefapirin
  • Cefapirina
  • Cefapirina [INN-Spanish]
  • Cefapirine
  • Cefapirine [INN-French]
  • Cefapirinum
  • Cefapirinum [INN-Latin]
  • Cefaprin
  • Cephalosporanic acid, 7-(2-(4-pyridylthio)acetamido)-
  • Cephapirin
  • Cephapirine
  • EINECS 244-466-5
  • HSDB 3215
  • UNII-89B59H32VN

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6R-trans)-
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester)
  • Cefapirin

Registry Numbers

CAS Registry Number

  • 21593-23-7

FDA UNII

  • 89B59H32VN

Related Registry Number

  • 24356-60-3 (mono-hydrochloride salt)

System Generated Number

  • 0021593237

Structure Descriptors

InChI

1S/C17H17N3O6S2/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)/t13-,16-/m1/s1

InChIKey

UQLLWWBDSUHNEB-CZUORRHYSA-N

Smiles

N12[C@@H]([C@@H](NC(CSc3ccncc3)=O)C2=O)SCC(=C1C(O)=O)COC(C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 514ug/kg/9D-I (0.514mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" Drug Intelligence and Clinical Pharmacy. Vol. 19, Pg. 553, 1985.
mouse LD50 intraperitoneal 8899mg/kg (8899mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
mouse LD50 intravenous > 7602mg/kg (7602mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
mouse LD50 oral 26088mg/kg (26088mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: IRRITABILITY

BEHAVIORAL: ATAXIA
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
mouse LD50 subcutaneous 13556mg/kg (13556mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
rat LD50 intraperitoneal 7850mg/kg (7850mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
rat LD50 intravenous 6048mg/kg (6048mg/kg) SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
rat LD50 oral 16356mg/kg (16356mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: IRRITABILITY
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.
rat LD50 subcutaneous > 14400mg/kg (14400mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 21, Pg. 279, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.15E+00 (none)   EXP
Water Solubility 1030 mg/L 25 EST
Vapor Pressure 1.44E-15 mm Hg 25 EST
Henry's Law Constant 1.11E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

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