Cefotetan

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
Clinical data
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Injection
ATC code
Legal status
Legal status
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.067.337
Chemical and physical data
FormulaC17H17N7O8S4
Molar mass575.60 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)C3S/C(S3)=C(/C(=O)N)C(=O)O)CSc4nnnn4C)C(=O)O
InChI
  • InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1 Y
  • Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N Y
 NY (what is this?)  (verify)

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

Adverse effects

The chemical structure of cefotetan, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[1]

Spectrum of bacterial susceptibility

Cefotetan has a broad spectrum of activity and has been used to treat bacterial infections of the bone, skin, urinary tract, and lower respiratory tract. Notable species include Bacteroides, Streptococcus, and Escherichia. The following represents MIC susceptibility data for a few medically significant bacteria.[2]

  • Escherichia coli: 0.06 µg/mL
  • Bacteroides fragilis: ≤0.06 µg/mL - 512 µg/mL
  • Clostridium perfringens: 1 µg/mL - 4 µg/mL

References
  1. Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
  2. "Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Toku-e.
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