Cefamandole

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Cefamandole
Cefamandole.svg
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
Clinical data
Trade names former Mandol
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601206
Pregnancy cat.
Legal status
Routes Intramuscular, intravenous
Pharmacokinetic data
Protein binding 75%
Half-life 48 minutes
Excretion Mostly renal, as unchanged drug
Identifiers
CAS number 34444-01-4 YesY 42540-40-9
ATC code J01DC03
PubChem CID 456255
DrugBank DB01326
ChemSpider 401748 YesY
UNII 5CKP8C2LLI YesY
KEGG D02344 YesY
ChEBI CHEBI:3480 YesY
ChEMBL CHEMBL1146 YesY
Chemical data
Formula C18H18N6O5S2 
Mol. mass 462.505 g/mol
 YesY (what is this?)  (verify)

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.

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)(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.


Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.

  • Escherichia coli: 0.12 - 400 μg/ml
  • Haemophilus influenzae: 0.06 - >16 μg/ml
  • Staphylococcus aureus: 0.1 - 12.5 μg/ml

[1]

CO2 is generated during the normal constitution of cefamandole and ceftazidim, resulting in an explosive-like reaction in syringes.[2]

References[edit]

  1. ^ http://www.toku-e.com/Assets/MIC/Cefamandole%20sodium%20salt.pdf
  2. ^ 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.