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
• Article Data: 3

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

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 56796-39-5 differently. You can refer to the following data:
1. Semi-synthetic antibiotic derived from Cephamycin. Antibacterial
2. Cefmetazole sodium is used clinically in combination with Tanreqing for the treatment of Pulmonary infections like Senile Emphysema and other acute bacterial infections.

Definition

ChEBI: An organic sodium salt that is the sodium salt of cefmetazole.

Brand name

Zefazone (Pharmacia & Upjohn）.

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

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%.