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Cefmetazole

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Chemical compound

Pharmaceutical compound

Cefmetazole
Clinical data


AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
ATC code	J01DC09 (WHO)
Identifiers
IUPAC name (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	56796-20-4^Y
PubChemCID	42008
DrugBank	DB00274^Y
ChemSpider	38311^Y
UNII	3J962UJT8H
KEGG	D00910^Y
ChEBI	CHEBI:3489^Y
ChEMBL	ChEMBL1201195^N
CompTox Dashboard(EPA)	DTXSID7022756
ECHA InfoCard	100.054.877
Chemical and physical data
Formula	C₁₅H₁₇N₇O₅S₃
Molar mass	471.53 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O
InChI InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1^Y Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N^Y
^NY (what is this?) (verify)

Cefmetazole is acephamycin antibiotic, usually grouped with the second-generation cephalosporins.

Adverse effects

[edit]

The chemical structure of cefmetazole, 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 theenzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced bydisulfiram, due to inhibition ofaldehyde dehydrogenase.^[1]

Spectrum of bacterial susceptibility

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Cefmetazole is a broad-spectrum cephalosporin antimicrobial and has been effective in treating bacteria responsible for causing urinary tract and skin infections.^{[citation needed]}The following represents MIC susceptibility data for a few medically significant microorganisms.

Bacteroides fragilis: 0.06 - >256 μg/ml
Clostridioides difficile: 8 - >128 μg/ml
Staphylococcus aureus: 0.5 - 256 μg/ml (includesMRSA)^[2]

References

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^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.
^"Cefmetazole, free acid Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data"(PDF).The Antimicrobial Index. TOKU-E. 6 January 2020.

Antibacterials active on thecell wall andenvelope (J01C-J01D)

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)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ /Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems /Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization:Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking:Ramoplanin^§

Intracellular

InhibitPG subunit synthesis and transport:NAM synthesis inhibition
- Fosfomycin
DADAL/AR inhibitors
- Cycloserine
- Terizidone
bactoprenol inhibitors
- Bacitracin

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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