Cefamandole

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.

Cefamandole

Clinical data
Trade names	former Mandol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Pregnancy category	AU: B1
Routes of administration	Intramuscular, intravenous
ATC code	J01DC03 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: Discontinued
Pharmacokinetic data
Protein binding	75%
Elimination half-life	48 minutes
Excretion	Mostly renal, as unchanged drug
Identifiers
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
CAS Number	34444-01-4 Y 42540-40-9
PubChem CID	456255
DrugBank	DB01326 Y
ChemSpider	401748 Y
UNII	5CKP8C2LLI
KEGG	D02344 Y
ChEBI	CHEBI:3480 Y
ChEMBL	ChEMBL1146 Y
CompTox Dashboard (EPA)	DTXSID7022750
ECHA InfoCard	100.047.285
Chemical and physical data
Formula	C18H18N6O5S2
Molar mass	462.50 g·mol−1
3D model (JSmol)	Interactive image
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
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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. Vitamin K supplement is recommended during therapy, and consumption of ethanol and ethanol-containing substances is discouraged.

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 ceftazidime, potentially resulting in an explosive-like reaction in syringes.^[2]

See also

• Cefazolin
• Ceforanide