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Cefotetan

From Wikipedia, the free encyclopedia
Pharmaceutical drug
Pharmaceutical compound
Cefotetan
Clinical data
AHFS/Drugs.comConsumer Drug Information
Routes of
administration
Injection
ATC code
Legal status
Legal status
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.067.337Edit this at Wikidata
Chemical and physical data
FormulaC17H17N7O8S4
Molar mass575.60 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cefotetan is an injectableantibiotic of thecephamycin type for prophylaxis and treatment ofbacterial infections. It is often grouped together with second-generationcephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

Cefotetan was developed byYamanouchi. It is marketed outside Japan byAstraZeneca with the brand namesApatef andCefotan.

Adverse effects

[edit]

The chemical structure of cefotetan, like that of several other cephalosporins, contains anN-methylthiotetrazole (NMTT or 1-MTT)side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can causehypoprothrombinemia (likely due toinhibition of theenzymevitamin K epoxide reductase) and a reaction with ethanol similar to that produced bydisulfiram (Antabuse), due to inhibition ofaldehyde dehydrogenase.[1]

Spectrum of bacterial susceptibility

[edit]

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 includeBacteroides, Streptococcus, andEscherichia. 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

[edit]
  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. Retrieved2009-07-03.
  2. ^"Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data"(PDF). Toku-e.

External links

[edit]
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
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