56796-39-5

Basic information

• Product Name: Cefmetazole sodium
• Synonyms: Cefmetazone;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-, monosodium salt, (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-, monosodium salt, (6R-cis)-;Cefmetazole-Na;CS-1170 sodium salt;Metafar;Sodium cefmetazole;Cefmetazole sodium
• CAS NO: 56796-39-5
• Molecular Formula: C₁₅H₁₆N₇O₅S₃*Na
• Molecular Weight: 493.52
• EINECS: 1308068-626-2
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Interferes with Cell Wall SynthesisAntibiotics;Mechanism of Action;Penicillins and Cephalosporins (beta-Lactams);Spectrum of Activity
• Mol File: 56796-39-5.mol

Chemical Properties

• Appearance: White solid
• Density: 1.75 g/cm3
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble50mg/mL
• Water Solubility: Soluble in water
• Sensitive: Hygroscopic
• Merck: 14,1926
• CAS DataBase Reference: Cefmetazole sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Cefmetazole sodium(56796-39-5)
• EPA Substance Registry System: Cefmetazole sodium(56796-39-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42/43
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: XI0372200
• Hazardous Substances Data: 56796-39-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cefmetazole sodium is used as an antibiotic for the treatment of various bacterial infections. It is particularly effective against a wide range of gram-positive and some gram-negative bacteria, making it a valuable asset in combating resistant infections.
Used in Clinical Medicine:
Cefmetazole sodium is used in combination with Tanreqing for the treatment of pulmonary infections such as senile emphysema and other acute bacterial infections. Its synergistic action with Tanreqing enhances the therapeutic efficacy in managing these respiratory conditions.

Clinical Use

Cefmetazole (Zefazone) is a semisynthetic, third-generation,parenteral cephalosporin of the cephamycin group. Likeother cephamycins, the presence of the 7α-methoxyl groupconfers resistance to many β-lactamases. Cefmetazoleexhibits significantly higher potency against members ofthe Enterobacteriaceae family but lower activity againstBacteroides spp. than cefoxitin. It is highly active againstN. gonorrhoeae, including -lactamase–producing strains. Incommon with other cephamycins, cefmetazole is ineffectiveagainst indole-positive Proteus, Enterobacter, Providencia,Serratia, and Pseudomonas spp. Cefmetazole has the MTTmoiety associated with increased bleeding in certain highriskpatients. It has a plasma half-life of 1.1 hours.

InChI:InChI=1/C15H17N7O5S3.Na/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);/q;+1/p-1/t13?,15-;/m0./s1

Upstream product

• 56796-20-4 Cefmetazole 
• 957-68-6 7-Aminocephalosporanic acid 
• 949587-47-7 sodium 2-(cyanomethylthio)acetate 

Downstream Products

• 68233-01-2 (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 benzyl ester 

Relevant articles and documents

PROCESS FOR PREPARING CEFMETAZOLE SODIUM

The present invention relates to a method for manufacturing cefmetazole sodium. More specifically, the present invention relates to a method for manufacturing cefmetazole sodium by crystallization, wherein the method comprises the following steps: dissolving cefmetazole acid and sodium salt in an organic solvent; and then performing crystallization of a product after the reaction by using a crystallization solvent. Thus, the method can manufacture cefmetazole sodium without using lyophilization, which is an existing manufacturing method, while shortening the time and without additional equipment.COPYRIGHT KIPO 2020

A head spore US[...] synthesis and purification method

The invention discloses a cefmetazole sodium preparation method. The cefmetazole sodium preparation method comprises the following steps: preparing 7beta-chloroacetamide- 7alpha-methoxyl-3-(1-methyl-1H-tetrazole-5-mercaptomethy)-3-cephem-4-carboxylic acid through silanization, halogenation, methoxylation and secondary silanization of 7beta-dichloroacetamido-3-(1-methyl-1H-tetrazole-5-mercaptomethy)-3-cephem-4-carboxylic acid triethylamine salt serving as a starting material, and then carrying out chain extension and acid and salt formation, thus obtaining cefmetazole sodium. The cefmetazole sodium preparation method has the advantages that the yield is high and reaches 55-65%, the product is high in purity, the 7beta-dichloroacetamido-3-(1-methyl-1H-tetrazole-5-mercaptomethy)-3-cephem-4-carboxylic acid triethylamine salt is used for replacing 7-MAC and serves as the starting material, the raw material is convenient in source, low in cost and environmentally friendly, the product is high in purity and suitable for industrial production. and the like.

Preparation method of cefmetazole

The invention relates to a preparation method of cefmetazole. The preparation method comprises the steps of adopting a one-pot method containing 7-ACA, 1-methyl-5-tetrazole-thione and chloroacetyl chloride, obtaining 7-DCT, then using seven-position methoxy groups of sodium methylate and tert-butyl hypochlorite, and obtaining methoxy cephalosporin mother nuclei which are shared mother nuclei. The cefmetazole can serve as four methoxy cephalosporin products, namely cefminox, cefmetazole, cephalosporin and cefotetan disodium, three steps are omitted, the processing steps are greatly shortened, cost is lowered, and the overall yield is raised to 70%.