Cefmetazole

Base Information

• Chemical Name: Cefmetazole
• CAS No.: 56796-20-4
• Molecular Formula: C₁₅H₁₇N₇O₅S₃
• Molecular Weight: 471.542
• Hs Code.: 2941906000
• European Community (EC) Number: 260-384-2
• UNII: 3J962UJT8H
• DSSTox Substance ID: DTXSID7022756
• Nikkaji Number: J14.542D
• Wikipedia: Cefmetazole
• Wikidata: Q5057238
• NCI Thesaurus Code: C65297
• Metabolomics Workbench ID: 42668
• ChEMBL ID: CHEMBL1201195
• Mol file: 56796-20-4.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7S)- (9CI);CS 1170;SKF 83088;U 72791;U 72791a;

Chemical Property of Cefmetazole

Chemical Property:

• Melting Point: 163-165oC
• Refractive Index: 1.797
• PKA: 2.65±0.50(Predicted)
• PSA: 239.23000
• Density: 1.75 g/cm³
• LogP: -0.39952
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated)
• Water Solubility.: Soluble in water
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 471.04533019
• Heavy Atom Count: 30
• Complexity: 818

Purity/Quality:

99% ^*data from raw suppliers

Cefmetazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
• Isomeric SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
• Recent ClinicalTrials: Trial of Antibiotic Prophylaxis in Elective Laparoscopic Colorectal Surgery: Oral and Systemic Versus Systemic Antibiotics
• Recent NIPH Clinical Trials: Study on pharmacokinetics of cefmetazole for over-weight or under-weight patients
• Description: Cefmetazole is a cephamycin with a nonaromatic side chain at C-7. In addition to a fairly characteristic second-generation cephalosporin antimicrobial spectrum, it possess fairly significant anti-antiaerobic activity. The ejection of its C-3 side chain leads to alcohol intolerance of the disulfuram type and prolonged clotting times.
• Uses: Semi-synthetic antibiotic derived from Cephamycin. Antibacterial. A broad spectrum second generation cephalosporin antibiotic

Technology Process of Cefmetazole

There total 12 articles about Cefmetazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cyanomethylmercapto acetyl chloride (52069-55-3) + C17H30N6O4S2Si2 → Cefmetazole (56796-20-4,82263-66-9)

Guidance literature:

cyanomethylmercapto acetyl chloride; C₁₇H₃₀N₆O₄S₂Si₂; With triethylamine; In chloroform; at -20 - -10 ℃; for 0.5h; Green chemistry;

With hydrogenchloride; In water; at 15 ℃; for 0.5h; Green chemistry;

Reference yield:

C23H33N7O8S3Si → Cefmetazole (56796-20-4,82263-66-9)

Guidance literature:

With hydrogenchloride; In water; at 15 ℃; for 0.333333h;

Reference yield:

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → Cefmetazole (56796-20-4,82263-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) MeOH, THF, (ii) /BRN= 982526/, (iii) /BRN= 3552389/, tBuOCl, ClCH₂CH₂Cl

2: PhNHNH₂ / 1,2-dichloro-ethane

3: PhNEt₂ / 1,2-dichloro-ethane

With phenylhydrazine; N,N-diethylaniline; In 1,2-dichloro-ethane;

DOI:10.7164/antibiotics.29.969

upstream raw materials:

cyanomethylmercapto acetyl chloride

(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

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ³-cephem-4-carboxylate

(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 raw materials:

cefmetazole sodium

(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

Refernces

• 1、 -. "Preparation method of cefmetazole acid". . . Retrieved 2017/03/28.
• 2、 Yanagisawa,Fukushima,Ando,Nakao. "Synthesis of 7α substituted cephalosporins. V. Novel oxidation procedure for syntheses of 7α methoxycephalosporins and 6α methoxypenicillins". . p. 969 - 972. Retrieved 2007/10/07.