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
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Pregnancy cat.	B1 (AU)
Legal status	POM (UK) Discontinued (US)
Routes	Intramuscular, intravenous
Pharmacokinetic data
Protein binding	75%
Half-life	48 minutes
Excretion	Mostly renal, as unchanged drug
Identifiers
CAS number	34444-01-4 Y 42540-40-9
ATC code	J01DC03
PubChem	CID 456255
DrugBank	DB01326
ChemSpider	401748 Y
UNII	5CKP8C2LLI Y
KEGG	D02344 Y
ChEBI	CHEBI:3480 Y
ChEMBL	CHEMBL1146 Y
Chemical data
Formula	C18H18N6O5S2
Mol. 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 Y Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N Y
Y (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.

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)(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.

Report

CO2 is generated during the normal constitution of cefamandole & ceftazidim resulting in explosive like reaction in syringe