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Substance Name: Cefoxitin sodium [USAN:USP:BAN:JAN]
RN: 33564-30-6
UNII: Q68050H03T
InChIKey: GNWUOVJNSFPWDD-XMZRARIVSA-M

Note

  • A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

Molecular Formulas

  • C16-H16-N3-Na-O7-S2
  • C16-H16-N3-O7-S2.Na
  • C16-H17-N3-O7-S2.Na

Molecular Weight

  • 449.4384
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antibiotics
  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Cefoxitin sodium [USAN:USP:BAN:JAN]

Synonyms

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, sodium salt, (6R-cis)-
  • Betacef
  • Cefoxil
  • Cefoxitin
  • Cefoxitin and dextrose in duplex container
  • Cefoxitin sodium
  • Cefoxitin sodium salt
  • Cefoxotin sodium
  • Cenomycin
  • EINECS 251-574-6
  • L 620388
  • Mefoxin
  • Mefoxin in dextrose 5% in plastic container
  • Mefoxin in plastic container
  • Mefoxin in sodium chloride 0.9% in plastic container
  • Mefoxitin
  • Merxin
  • MK 206
  • Monosodium cefoxitin
  • Sodium (6R,7S)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate carbamate (ester)
  • UNII-Q68050H03T

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, monosodium salt, (6R-cis)-
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, sodium salt, (6R-cis)-
  • Sodium (6R-cis)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Registry Numbers

CAS Registry Number

  • 33564-30-6

FDA UNII

  • Q68050H03T

System Generated Number

  • 0033564306

Molecular Formulas

Molecular Formulas

  • C16-H16-N3-Na-O7-S2
  • C16-H16-N3-O7-S2.Na
  • C16-H17-N3-O7-S2.Na

Molecular Formula Fragments

  • C16-H16-N3-O7-S2
  • C16-H17-N3-O7-S2
  • COMPONENT
  • Na

Structure Descriptors

InChI

InChI=1S/C16H17N3O7S2.Na/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19;/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22);/q;+1/p-1/t14-,16+;/m1./s1

InChIKey

GNWUOVJNSFPWDD-XMZRARIVSA-M

Smiles

[Na+].CO[C@]1(NC(=O)Cc2cccs2)[C@H]3SCC(=C(N3C1=O)C(=O)[O-])COC(=O)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 10000mg/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 410, 1982.
man TDLo intravenous 100mg/kg/2D-I (100mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Southern Medical Journal. Vol. 80, Pg. 274, 1987.
man TDLo intravenous 229mg/kg/4D-I (229mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: APLASTIC ANEMIA		 Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 816, 1983.
mouse LD50 intravenous 4970mg/kg (4970mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 291, 1980.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.
mouse LD50 subcutaneous 9250mg/kg (9250mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.
rat LD50 intravenous 8580mg/kg (8580mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 oral > 10gm/kg (10000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 123, 1980.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.