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Cefamandole

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Cefamandole
Clinical data
Trade namesformer Mandol
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601206
Pregnancy
category
Routes of
administration
Intramuscular,intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding75%
Eliminationhalf-life48 minutes
ExcretionMostlyrenal, as unchanged drug
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.047.285Edit this at Wikidata
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
  (verify)

Cefamandole (INN, also known ascephamandole) is a second-generationbroad-spectrumcephalosporinantibiotic. The clinically used form of cefamandole is theformateestercefamandole nafate, aprodrug which is administeredparenterally. Cefamandole isno longer available in the United States.

The chemical structure of cefamandole, like that of several other cephalosporins, contains anN-methylthiotetrazole (NMTT or 1-MTT)side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can causehypoprothrombinemia (likely due toinhibition of theenzymevitamin K epoxide reductase) and a reaction withethanol similar to that produced bydisulfiram (Antabuse), due to inhibition ofaldehyde 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

[edit]

References

[edit]
  1. ^"Cefamandole sodium salt Susceptibility and 0.5 - 32 Minimum Inhibitory Concentration (MIC) Data"(PDF).The Antimicrobial Index. TOKU-E. 6 January 2020.
  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. Retrieved2009-07-03.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other
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