61270-58-4

Basic information

• Product Name: Cefonicid
• Synonyms: 7-beta(r*)))-;amino)-8-oxo-3-(((1-sulfomethyl)-1h-tetrazol-5-yl)thio)methyl)-,(6r-(6-alpha,;CEFONICID;(7r)-7-(2-hydroxy-2-phenylacetylamino)-6-oxo-3-{[1-(sulfomethyl)(1,2,3,4-tetraazol-5-ylthio)]methyl}-2h,7h,7ah-azetidino[2,1-b]1,3-thiazine-4-carboxylic acid;(6R,7R)-7-[[(2R)-2-Hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;[6R-[6α，7β(R^^)]]-7- [(2-Hydroxy-2-phenylacetyl)amino]-3-[(1-sulfomethyl-1H-tetrazol-5-y1)tlfiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-enr2-carboxylic acid;Cefodie;Monocid
• CAS NO: 61270-58-4
• Molecular Formula: C₁₈H₁₈N₆O₈S₃
• Molecular Weight: 542.57
• Product Categories: API;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 61270-58-4.mol

Chemical Properties

• Appearance: /
• Density: 1.92 g/cm³
• Refractive Index: 1.852
• PKA: -1.23±0.50(Predicted)
• CAS DataBase Reference: Cefonicid(CAS DataBase Reference)
• NIST Chemistry Reference: Cefonicid(61270-58-4)
• EPA Substance Registry System: Cefonicid(61270-58-4)

Safety Data

• Hazardous Substances Data: 61270-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cefonicid is used as an antibiotic for treating bacterial infections. Its application is due to its ability to target and eliminate a wide range of bacteria, making it a valuable tool in the treatment of various infections.
Used in Medical Treatments:
Cefonicid is used as a therapeutic agent for combating bacterial infections, particularly those caused by Gram-negative and some Gram-positive bacteria. Its application is attributed to its effectiveness in treating infections and its longer half-life, which may reduce the frequency of administration.

Antimicrobial activity

Activity against Gram-positive and Gram-negative organisms in vitro is depressed by the presence of 50% serum. It is highly bound to plasma protein (98%) and has an extended plasma half-life of 4.5–5 h. A 1 g intramuscular dose achieves a mean peak plasma concentration of around 83 mg/L. Following a 1 g intravenous bolus dose, mean peak plasma concentrations of 130–300 mg/L have been reported. In patients treated for community-acquired pneumonia, concentrations of 2–4 mg/L have been found in sputum. It is predominantly excreted by renal secretion, 83–89% being recovered unchanged in the urine over 24 h. Plasma half-life is linearly related to creatinine clearance. As a result of its high protein binding it is not removed by hemodialysis. It is generally well tolerated; pain on injection, rash and positive Coombs’ test are reported in some patients. It has been used to treat respiratory, soft tissue and urinary infections. Available in Italy.

Synthesis

Cefonicid, 7-D-mandelamido-3-[[(1-sulfomethyl]-1H-tetrazol-5-yl]thio] methyl]- 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.26), is structurally similar to cefamandole and differs in the presence of a sulfonic acid group in the methyl substituent of the tetrazol ring. It is synthesized by a method analogous to that of the synthesis of cefamandole.

InChI:InChI=1/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1

Upstream product

• 20698-91-3 (R)-methyl mandelate 
• 61270-71-1 7-amino-3-(1-sulfomethyl-1H-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid 

Relevant articles and documents

Coupling of Site-Directed mutagenesis and immobilization for the rational design of more efficient biocatalysts: The case of immobilized 3G3K PGA from E. coli

We have investigated the synthetic performance of the immobilized 3G3K mutant of the Penicillin G acylase (PGA) from E. coli obtained by site-directed mutagenesis. The 3G3K mutant, characterized by a tag consisting of three lysines alternating with three

Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid

The influence of the substrate structure on the catalytic properties of penicillin G acylase (PGA) from Escherichia coli in kinetically controlled acylations has been studied. In particular, the affinity of different β-lactam nuclei towards the active site has been evaluated considering the ratio between the rate of synthesis (vs) and the rate of hydrolysis of the acylating ester (vhl). 7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-(1-sulfomethyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (7-SACA) showed a good affinity for the active centre of PGA. The enzymatic acylation of these nuclei with R-methyl mandelate has been studied in order to evaluate different approaches for the enzymatic synthesis of cefonicid. The best results have been obtained in the acylation of 7-SACA. Cefonicid (8) was recovered from the reaction mixture as the disodium salt in 65% yield and about 95% of purity. Furthermore, through acylation of 7-ACA, a "one-pot" chemo-enzymatic synthesis was carried out starting from cephalosporin C using three enzymes in sequence: D-amino acid oxidase (DAO), glutaryl acylase (GA) and PGA. Cefonicid disodium salt was obtained in three steps, avoiding any intermediate purification, in 35% overall yield and about 94% purity. This approach presents several advantages compared with the classical chemical processes.