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Cefamandole
Systematic (IUPAC) name
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-
3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS number 34444-01-4 42540-40-9 (nafate)
ATC code J01DC03
PubChem 456255
ChemSpider 401748
Chemical data
Formula C 18H18N6O5S2  
Mol. mass 462.505 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Protein binding 75%
Metabolism  ?
Half life 48 minutes
Excretion Mostly renal, as unchanged drug
Therapeutic considerations
Pregnancy cat. B1(AU)
Legal status POM (UK) Discontinued (US)
Routes Intramuscular, intravenous
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Cefamandole (INN, also known as cephamandole) is a second-generation broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally.

Cefamandole is no longer available in the United States.

Adverse effects

The chemical structure of cefamandole, 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]

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. pp. 847. ISBN 0-07-143763-0. http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847. Retrieved 2009-07-03.  
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