Cefonicid

Base Information

• Chemical Name: Cefonicid
• CAS No.: 61270-58-4
• Molecular Formula: C18H18 N6 O8 S3
• Molecular Weight: 542.574
• UNII: 6532B86WFG
• DSSTox Substance ID: DTXSID7022758
• Nikkaji Number: J18.085H
• Wikipedia: Cefonicid
• Wikidata: Q5057286
• NCI Thesaurus Code: C65299
• Metabolomics Workbench ID: 43497
• ChEMBL ID: CHEMBL1601
• Mol file: 61270-58-4.mol

Synonyms:Cefonicid;Cefonicid Disodium Salt;Cefonicid Monosodium;Cefonicid Monosodium Salt;Cefonicid, Sodium;Monocid;SK and F 75073;SK and F-75073;SK and F75073;SKF 75073 2;SKF-75073-2;SKF750732;Sodium Cefonicid

Chemical Property of Cefonicid

Chemical Property:

• PKA: -1.23±0.50(Predicted)
• PSA: 263.89000
• Density: 1.92 g/cm³
• LogP: 0.49230
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 542.03482507
• Heavy Atom Count: 35
• Complexity: 999

Purity/Quality:

99%, ^*data from raw suppliers

Cefonicid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)O)C(=O)O)CSC4=NN=NN4CS(=O)(=O)O
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)O)C(=O)O)CSC4=NN=NN4CS(=O)(=O)O
• Description: Cefonicid has an unesterified D-mandelic acid moiety at C-7 and a methylsulfothiotetrazole group at C-3. The latter is related to the MTT moiety mentioned above under cefamandole nafate; however, the clotting problems and Antabuse-like side effects associated with MTT have not been reported with cefonicid. The extra acid group in the C-3 side chain leads to this molecule being sold as an injectable disodium salt. Pain and discomfort at IM sites is experienced by some patients, as is a burning sensation and phlebitis. Cefonicid has a longer half-life than the other members of its group but achieves this at the price of somewhat lower potency against Gram-positive bacteria and aerobes. The drug is somewhat unstable, needs to be protected from light and heat, and may yellow or darken. If modest, however, this does not necessarily mean that the potency has decreased significantly, but overt precipitation does. Kirby-Bauer disk testing may overestimate the sensitivity of β-lactamase–producing bacteria to this agent, so some extra caution in interpretation of laboratory results is required.
• Uses: A semi-synthetic cephalosporin antibiotic related to Cefamandole. Antibacterial

Technology Process of Cefonicid

There total 2 articles about Cefonicid 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:

(R)-methyl mandelate (20698-91-3) + 7-amino-3-(1-sulfomethyl-1H-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (61270-71-1) → (R)-Mandelic Acid (611-71-2) + cefonicid (61270-58-4)

Guidance literature:

With immobilized penicillin G acylase from Escherichia coli; In methanol; phosphate buffer; at 4 ℃; for 4h; pH=5.5; Further Variations:; pH-values; Solvents; Product distribution; Kinetics;

DOI:10.1002/adsc.200404136

Reference yield:

(R)-methyl mandelate (20698-91-3) + 7-amino-3-(1-sulfomethyl-1H-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (61270-71-1) → cefonicid (61270-58-4)

Guidance literature:

With 3G₃K penicillin G acylase immobilized on glyoxyl agarose; at 4 ℃; pH=6.5; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/ejoc.200801204

upstream raw materials:

(R)-methyl mandelate

7-amino-3-(1-sulfomethyl-1H-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Refernces

• 1、 Terreni, Marco,Tchamkam, Joseph Gapesie,Sarnataro, Umberto,Rocchietti, Silvia,Fernandez-Lafuente, Roberto,Guisan, Jose M.. "Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid". . p. 121 - 128. Retrieved 2007/10/03.