Cefamandole

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
Clinical data
Trade names	former Mandol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Pregnancy category	AU: B1
Routes of administration	Intramuscular, intravenous
Legal status
Legal status	UK: POM (Prescription only) Discontinued (US)
Pharmacokinetic data
Protein binding	75%
Biological half-life	48 minutes
Excretion	Mostly renal, as unchanged drug
Identifiers
CAS Number	34444-01-4 42540-40-9
ATC code	J01DC03 (WHO)
PubChem	CID 456255
DrugBank	DB01326
ChemSpider	401748
UNII	5CKP8C2LLI
KEGG	D02344
ChEBI	CHEBI:3480
ChEMBL	CHEMBL1146
Chemical data
Formula	C18H18N6O5S2
Molar mass	462.505 g/mol
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4C)C(=O)O
InChI InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1 Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N
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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.

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]

See also

• Cefazolin
• Ceforanide

References

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.