56796-20-4

Basic information

• Product Name: Cefmetazole
• Synonyms: (6r;5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((((cyanomethyl)thio)a;cs1170;CEFMETAZOLE SODIUM SALT;Cefatrixine;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)-;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)-;SKF 83088
• CAS NO: 56796-20-4
• Molecular Formula: C₁₅H₁₇N₇O₅S₃
• Molecular Weight: 471.54
• EINECS: 260-384-2
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Pharmaceutical intermediate;Medicine intermediate
• Mol File: 56796-20-4.mol

Chemical Properties

• Melting Point: 163-165?C
• Appearance: /
• Density: 1.4380 (rough estimate)
• Refractive Index: 1.7400 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly, Heated)
• PKA: 2.65±0.50(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: Cefmetazole(CAS DataBase Reference)
• NIST Chemistry Reference: Cefmetazole(56796-20-4)
• EPA Substance Registry System: Cefmetazole(56796-20-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: XI0372200
• Hazardous Substances Data: 56796-20-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cefmetazole is used as a semi-synthetic antibiotic derived from Cephamycin for its antibacterial properties. It is effective against a wide range of bacteria, making it a valuable treatment option for various infections.
Used in Medical Treatments:
Cefmetazole is used as a broad-spectrum antibiotic for treating infections caused by both aerobic and anaerobic bacteria. Its effectiveness against a variety of bacterial strains makes it a useful tool in combating infections and promoting recovery in patients.

Antimicrobial activity

It is active against Pr. mirabilis, Pr. vulgaris, Morganella morganii, Yersinia spp.and most anaerobes. S. marcescens is moderately susceptible, but Ps. aeruginosa and E. faecalis are resistant. It is active against Mycobacterium fortuitum and some strains of M. chelonei. It is resistant to a wide range of β-lactamases. The serum concentration at the end of a 1 g intravenous infusion is around 77 mg/L. Plasma protein binding is 68%. It is principally excreted in the urine with a plasma half-life of c. 1.3 h; 70% is recovered over the first 6 h. In patients whose creatinine clearance is less than 10 mL/min, plasma levels are elevated and the plasma half-life is increased to around 15 h. Side effects associated with the methylthiotetrazole group at position C-3 have been reported. Uses are similar to those of cefoxitin, but it is not widely available.

InChI:InChI=1/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

Upstream product

• 52069-55-3 cyanomethylmercapto acetyl chloride 
• 60638-56-4 (6R)-7t-amino-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; benzyl-trimethyl-ammonium salt 
• 56610-72-1 diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ³-cephem-4-carboxylate 
• 53090-86-1 7β-amino-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>ceph-3-em-4-oic acid benzhydryl ester 
• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 60445-97-8 (6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; benzyl-trimethyl-ammonium salt 
• 56023-19-9 (6R)-7t-(3,5-di-tert-butyl-4-hydroxy-benzylideneamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 

Downstream Products

• 56796-39-5 cefmetazole sodium 
• 56842-00-3 (6R)-7t-(2-cyanomethylsulfanyl-acetylamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; dicyclohexylamine salt 

Relevant articles and documents

Method for preparing cefmetazole acid

The invention relates to a method for preparing cefmetazole acid and belongs to the technical field of preparation of cephalosporin compounds. The method for preparing the cefmetazole acid disclosed by the invention comprises the following steps: taking 7beta-amino-3-(1-methyl-1H-tetrazole-5-S-methyl)-3-cephem-4-carboxylic acid (3-TZ) as an initial raw material, performing silanization protectionon carboxyl and amino, and performing methylation, condensation and acid hydrolysis reaction, thereby obtaining cefmetazole acid. The method disclosed by the invention is simple in process, low in cost and less in steps, ensure high product yield and purity, has energy-saving and environmental-friendly effects, adopts a recyclable solvent and thus is suitable for industrialized production.

Preparation method of cefmetazole acid

The invention relates to a preparation method of cefmetazole acid, belonging to the technical field of preparation of cephalosporin compounds. The preparation method of cefmetazole acid comprises the following steps: by using 7beta-amino-3-(1-methyl-1H-tetrazolyl-5-thiomethyl)-3-cephem-4-carboxylic acid (also called 3-TZ) as an initial raw material, carrying out silanization, tert-butyloxy carboxylation, methoxylation, condensation and acid hydrolysis reaction to obtain the cefmetazole acid (VI). The preparation method has the advantages of simple technique, low cost, high product yield and purity, energy saving and environment friendliness, and is suitable for industrial production.

Prodrug derivatives of carboxylic acid drugs

Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.

A new semisynthetic 7α methoxycephalosporin, CS-1170: 7β [[(cyanomethyl)thio]acetamido] 7α methoxy 3 [[(1 methyl 1H tetrazol 5 yl)thio]methyl] 3 cephem 4 carboxylic acid

The synthesis and antimicrobial activity of a new semisynthetic 7α methoxycephalosporin, 7β [[(cyanomethyl)thio]acetamido] 7α methoxy [[(1 methyl 1H tetrazol 5 yl)thio] methyl] 3 cephem 4 carboxylic acid (CS 1170), are described. This compound shows interesting antibacterial activity when compared to cefoxitin and cephalothin.