Cefpirome

Base Information

• Chemical Name: Cefpirome
• CAS No.: 98753-19-6
• Molecular Formula: C22H22N6O5S2^.H2SO4
• Molecular Weight: 612.665
• European Community (EC) Number: 685-392-7
• UNII: S72Q2F09HY
• DSSTox Substance ID: DTXSID2048244
• Wikipedia: Cefpirome
• NCI Thesaurus Code: C79563
• Metabolomics Workbench ID: 49580
• ChEMBL ID: CHEMBL65794
• Mol file: 98753-19-6.mol

Synonyms:3-((2,3-cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylate;cefpirome;cefpirome sulfate;Cefrom;HR 810;HR-810;Metran

Chemical Property of Cefpirome

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 198-202 oC(dec)
• PSA: 290.44000
• LogP: 0.29410
• Storage Temp.: Store at 0-5°C
• Solubility.: Soluble in DMSO
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 514.10931017
• Heavy Atom Count: 35
• Complexity: 955

Purity/Quality:

Cefpirome Sulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
• Isomeric SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
• Recent EU Clinical Trials: Cerebral microdialysis in neurointensive care patients to determine brain penetration of antibiotics. An open label explorative study.
• Description: Cefpirome sulfate is a new injectable cephalosporin indicated for the treatment of severe urinary and respiratory tract infections, including septicemia and nosocomial infections. Cefpirome sulfate is reported to be the first true fourth-generation cephalosporin due to its similar activities to third-generation antibiotics against Gram-positive bacteria and to first-generation antibiotics against Gram-negative bacteria. Its efficacy against P.aeruginosa is comparable to ceftazidime. The broad spectrum of activity includes Klebsiella, methicillin-sensitive staphylococci, penicillin-resistant pneumococci, E.coli which generates extended-spectrum beta-lactamases and multi-resistant organisms such as Citrobacter, Enterobacter and Serratia.
• Uses: A fourth generation cephalosporin antibiotic Fourth generation cephalosporin antibiotic

Technology Process of Cefpirome

There total 10 articles about Cefpirome 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: 99.0%

2,3-cyclopentenopyridine (533-37-9) + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + 7-Aminocephalosporanic acid (957-68-6) → cefpirome Sulfate (98753-19-6)

Guidance literature:

With sulfuric acid; for 0.0666667h; Time; Microwave irradiation;

Reference yield: 86.34%

C30H31N6O6S2(1+)*I(1-) → cefpirome Sulfate (98753-19-6)

Guidance literature:

With sulfuric acid; In methanol; water; at 32 ℃; pH=1.5; Temperature; Solvent;

Reference yield:

cefpirome (84957-29-9,97164-55-1,130431-30-0,92682-05-8) → cefpirome Sulfate (98753-19-6)

Guidance literature:

With sulfuric acid; In water; at 5 ℃; pH=1 - 2;

DOI:10.1080/00397911003629499

upstream raw materials:

p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide

C₂₄H₂₃N₃O₄S

cefpirome

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 -. "Synthesis method of cefpirome sulfate". . . Retrieved 2019/05/08.
• 2、 Duan, Xuemin,Lu, Yao,Han, Juan,Chen, Ligong,Zheng, Pengwu. "One-pot synthesis of cefpirome sulfate from GCLE". . p. 629 - 636. Retrieved 2011/04/12.