Cefamandole

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Cefamandole
Cefamandole.svg
Names
Trade namesformer Mandol
  • (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
Pregnancy
category
  • AU: B1
Routes of
use
Intramuscular, intravenous
External links
AHFS/Drugs.comMicromedex Detailed Consumer Information
US NLMCefamandole
MedlinePlusa601206
Legal
Legal status
  • UK: POM (Prescription only)
  • US: Discontinued
Pharmacokinetics
Protein binding75%
Elimination half-life48 minutes
ExcretionMostly renal, as unchanged drug
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ATC code
Chemical and physical data
FormulaC18H18N6O5S2
Molar mass462.50 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4C)C(=O)O
  • 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 checkY
  • Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N checkY

Cefamandole (INN, also known as cephamandole) is an 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.

It is in the second-generation cephalosporin family of medications.[1] 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[2]

CO2 is generated during the normal constitution of cefamandole and ceftazidime, potentially resulting in an explosive-like reaction in syringes.[3]

See also

References

  1. Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.
  2. "Cefamandole sodium salt Susceptibility and 0.5 - 32 Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. TOKU-E. 6 January 2020. Archived (PDF) from the original on 3 March 2016. Retrieved 5 August 2021.
  3. 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. Archived from the original on 2013-06-13. Retrieved 2009-07-03.