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Substance Name: Cefoxitin [USAN:INN:BAN]
RN: 35607-66-0
UNII: 6OEV9DX57Y
InChIKey: WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

Note

  • A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

Molecular Formula

  • C16-H17-N3-O7-S2

Molecular Weight

  • 427.4563
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Cefoxitin
  • Cefoxitin [USAN:INN:BAN]

MeSH Heading

  • Cefoxitin

Synonyms

  • (6R,7S)-3-(Hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid carbamate (ester)
  • Cefoxitin
  • Cefoxitina
  • Cefoxitina [INN-Spanish]
  • Cefoxitine
  • Cefoxitine [INN-French]
  • Cefoxitinum
  • Cefoxitinum [INN-Latin]
  • Cephoxitin
  • CFX
  • EINECS 252-641-2
  • Rephoxitin
  • UNII-6OEV9DX57Y

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)-, (6R,7S)-
  • 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)-, (6R-cis)-
  • Cefoxitin

Registry Numbers

CAS Registry Number

  • 35607-66-0

FDA UNII

  • 6OEV9DX57Y

System Generated Number

  • 0035607660

Structure Descriptors

InChI

1S/C16H17N3O7S2/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)/t14-,16+/m1/s1

InChIKey

WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

Smiles

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 > 10gm/kg (10000mg/kg)   Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978.
mouse LD50 intravenous 4970mg/kg (4970mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Chemotherapy Vol. 26(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978.
mouse LD50 subcutaneous 9250mg/kg (9250mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 26(Suppl,
rat LD50 intravenous 8580mg/kg (8580mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

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

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 26(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978.
rat LD50 subcutaneous > 10mg/kg (10mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 26(Suppl,
women TDLo intravenous 75mg/kg/18H-I (75mg/kg) BLOOD: LEUKOPENIA Annals of Internal Medicine. Vol. 92, Pg. 874, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Boiling Point 149.5 dec deg C   EXP
log P (octanol-water) -0.02 (none)   EXP
Water Solubility 105 mg/L 25 EST
Vapor Pressure 1.09E-15 mm Hg 25 EST
Henry's Law Constant 6.50E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.44E-10 cm3/molecule-sec 25 EST

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