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Cefmetazole

Cefmetazole structure

CAS No:
56796-20-4
Formula:
C15H17N7O5S3
Chemical Name:
Cefmetazole
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[2-[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7S)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R-cis)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7S)-;(6R,7S)-7-[[2-[(Cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;CS 1170;SKF 83088;Cefmetazole;U 72791a;U 72791
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White Solid

Solid

Cefmetazole is a second-generation cephalosporin antibiotic having N(1)-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure. It has a role as an antibacterial drug. It is a conjugate acid of a cefmetazole(1-).|A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.|Cefmetazole is a second-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. Cefmetazole binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted.

Cefmetazole Basic Attributes

Molecular Weight：

471.54

Exact Mass：

471.53

EC Number：

260-384-2

UNII：

3J962UJT8H

DSSTox ID：

DTXSID7022756

NCI Thesaurus Code：

C65297

ATC Code：

J - Antiinfectives for systemic use

HScode：

2941906000

Characteristics

PSA：

239

XLogP3：

-2.2

Density：

1.8±0.1 g/cm3

Melting Point：

163-165°C

Refractive Index：

1.798

Water Solubility：

soluble in water

Storage Conditions：

2-8°C

Toxicity：

Peritoneal-mouse LD50: 10233 mg/kg; intravenous-mouse LD50: 8690 mg/kg

Flammability characteristics：

Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-42/43

safety instructions：

26-36

RTECS Number：

XI0372200

Marks：

Storage features：

The warehouse is low-temperature, ventilated and dry

Precautionary statement(s)：

P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Danger|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

practically nontoxic

Toxicity Summary：

Oral LD50 in rats is 3,204 mg/kg. With other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Drug Information

Drug Indication：

For the treatment of infections caused by susceptible organisms.

Pharmacology：

Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Bioavailability is approximately 100% following intramuscular injection.

Metabolism/Metabolites：

No appreciable metabolism.

Biological Half-Life：

1.50 ±0.14 hours

Mechanism of Action：

The bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

MeSH Entry Terms：

Cefmetazole

Cefmetazole Use and Manufacturing

Semi-synthetic antibiotic derived from Cephamycin. Antibacterial.

Computed Properties

Molecular Weight:471.5
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:9
Exact Mass:471.04533019
Monoisotopic Mass:471.04533019
Topological Polar Surface Area:239
Heavy Atom Count:30
Complexity:818
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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