Cefotetan

Title: Cefotetan
CAS Registry Number: 69712-56-7
CAS Name: (6R,7S)-7-[[[4-(2-Amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (6R,7S)-7-[4-(carbamoylcarboxymethylene)-1,3-dithietane-2-carboxamido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula: C17H17N7O8S4
Molecular Weight: 575.62
Percent Composition: C 35.47%, H 2.98%, N 17.03%, O 22.24%, S 22.28%
Literature References: Broad-spectrum injectable semi-synthetic antibiotic derived from cephamycin C, q.v. Prepn: M. Iwanami et al., DE 2824559; eidem, US 4263432 (1979, 1981 both to Yamanouchi); eidem, Chem. Pharm. Bull. 28, 2629 (1980). Commercial-scale synthesis: M. Fujimoto et al., Org. Process Res. Dev. 8, 915 (2004). In vitro comparison of antibacterial activity: B. Chattopadhyay, J. C. Teli, J. Antimicrob. Chemother. 10, 151 (1982). Toxicity study: K. Imamura et al., Chemotherapy (Tokyo) 30, Suppl. 1, 212 (1982). Series of articles on pharmacology, clinical studies, toxicology: ibid. 1-947; J. Antimicrob. Chemother. 11, Suppl. A, 1-236 (1983). Review of antibacterial activity, pharmacokinetics, therapeutic use: A. Ward, D. M. Richards, Drugs 30, 382-426 (1985).
Derivative Type: Disodium salt
CAS Registry Number: 74356-00-6
Manufacturers' Codes: ICI-156834; YM-09330
Trademarks: Apatef (AstraZeneca); Cefotan (AstraZeneca); Ceftenon (Biochemie); Cepan (IBI); Darvilen (Schering AG)
Molecular Formula: C17H15N7Na2O8S4
Molecular Weight: 619.58
Percent Composition: C 32.95%, H 2.44%, N 15.82%, Na 7.42%, O 20.66%, S 20.70%
Properties: LD50 in male mice, rats (g/kg): 6.35, 8.48 i.v.; 8.12, 8.37 i.p.; >10 orally and s.c. both species (Imamura).
Toxicity data: LD50 in male mice, rats (g/kg): 6.35, 8.48 i.v.; 8.12, 8.37 i.p.; >10 orally and s.c. both species (Imamura)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephamycins.
Cefotiam Cefoxitin Cefozopran Cefpimizole Cefpiramide

Cefotetan
Cefotetan.svg
Systematic (IUPAC) name
(7S)-7-{[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)
1,3-dithietane-2-carbonyl]amino}-7-methoxy-
3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com Consumer Drug Information
Legal status  ?
Identifiers
CAS number 69712-56-7 YesY
ATC code J01DC05
PubChem CID 53025
DrugBank DB01330
ChemSpider 47904 YesY
UNII 48SPP0PA9Q YesY
KEGG D00260 N
ChEBI CHEBI:3499 N
ChEMBL CHEMBL474579 N
Chemical data
Formula C17H17N7O8S4 
Mol. mass 575.623 g/mol
 N (what is this?)  (verify)

Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

Cefotetan was developed by Yamanouchi. It is marketed outside Japan by AstraZeneca with the brand names Apatef and Cefotan.