Cefoselis sulfate CAS 122841-12-7

Introduction：Basic information about Cefoselis sulfate CAS 122841-12-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Cefoselis sulfate Basic information

• Product Name: Cefoselis sulfate
• Synonyms: CEFOSELIS SULFATE;FK 037;7-[[2-(2-amino-4-thiazolyl)-2-methoxyimino-1-oxoethyl]amino]-3-[[2-(2-hydroxyethyl)-3-imino-1-pyrazolyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R-(6alpha,7beta(Z)))-7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((2,3-dihydro-2-(2-hydroxyethyl)-3-imino-1H-pyrazol-1-yl)methyl)-8-oxo-5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sulfate;Winsef;(6R,7R,E)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((2-(2-hydroxyethyl)-3-imino-2,3-dihydropyrazol-1-yl)methyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, sulfate;FK 037 Sulfate;Cefoselis sulfate USP/EP/BP
• CAS: 122841-12-7
• MF: C19H24N8O10S3
• MW: 620.63
• EINECS: 1533716-785-6
• Product Categories: Inhibitors;Cefoselis sulfate and its intermediates
• Mol File: 122841-12-7.mol

Cefoselis sulfate Chemical Properties

• storage temp.: 4°C, protect from light, stored under nitrogen
• solubility: DMSO : 100 mg/mL (161.12 mM; Need ultrasonic)H2O : 14.29 mg/mL (23.02 mM; Need ultrasonic)
• form: Powder
• color: White to off-white
• InChIKey: LZOLCSVRFKCSEM-GZRJWVSENA-N
• SMILES: S(O)(O)(=O)=O.C(C1=C(CS[C@]2([H])[C@H](NC(=O)/C(/C3=CSC(N)=N3)=N\OC)C(=O)N12)CN1C=CC(=N)N1CCO)(=O)O |&1:10,12,r|
• CAS DataBase Reference: 122841-12-7(CAS DataBase Reference)

Cefoselis sulfate Usage And Synthesis

Description

Cefoselis is a new fourth-generation cephalosporin and was launchedin Japan as a parenteral antibiotic for a variety of infections includingStaphylococcus aureus (particularly the methicillin-resistant MRSA) andPseudornonas aeruginosa. It can be prepared in 3 related ways, all using 2-pyrazolomethyl-3-cephem-4-carboxylic as the key intermediate. In preclinicalstudies, Cefolesis had better MIC50s than Ceftazidime against Streptococcuspneurnoniae or Staphflococcus aureus (methicillin-sensitive MSSA or resistantMRSA) and showed significant antibacterial activity against Citrobacter andEnterobacter.
Cefolesis is well tolerated in clinical studies, being eliminated mainly viaglomerular filtration in humans.

Originator

Fujisawa (Japan)

Uses

Cefoselis sulfate belongs to the fourth generation of ultra-broad-spectrum cephalosporins, exhibiting potent antibacterial activity against Gram-positive bacteria including staphylococci, pneumococci, and streptococci, as well as Gram-negative bacteria such as Pseudomonas, Escherichia coli, Klebsiella pneumoniae, Enterobacter species, and Serratia marcescens. It is primarily indicated for infections caused by susceptible bacteria, including respiratory tract infections, urinary tract infections, biliary tract infections, and intra-abdominal infections.
Cefoselis sulfate exhibits high sensitivity against Streptococcus pneumoniae, group ABC streptococci, methicillin-susceptible Staphylococcus aureus, and non-enzyme-producing staphylococci. Its antimicrobial activity surpasses that of cefotiam, cefoperazone, cefotaxime, and ceftriaxone. It exhibits potent antibacterial activity against Streptococcus pyogenes, Streptococcus viridans, and Streptococcus bovis, with an MIC90 of 0.06 mg/L. It demonstrates good antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), with an MIC90 of 16 mg/L, exhibiting superior activity to most cephalosporin antibiotics.

Definition

ChEBI: Cefoselis sulfate is an azaheterocycle sulfate salt. It is functionally related to a member of cefoselis.

Brand name

Wincef

References

[1] K OHTAKI. Cefoselis, a beta-lactam antibiotic, easily penetrates the blood-brain barrier and causes seizure independently by glutamate release.[J]. Journal of Neural Transmission, 2004, 111 12: 1523-1535. DOI:10.1007/s00702-004-0177-0. 
[2] PRZEMYSŁAW ZALEWSKI   Anna J  Judyta Cielecka Piontek. Stability of cefoselis sulfate in aqueous solutions[J]. Reaction Kinetics, Mechanisms and Catalysis, 2012, 108 2: 285-292. DOI:10.1007/s11144-012-0523-4.
[3] ZHU, D., et al., In vitro activities of cefoselis compared to β-lactams and other antibacterial agents aganst gram-positive and gram-negative clinical isolates. Chinese Journal of Infection and Chemotherapy, 2011. 4: p. 002.
[4] ANNA KING   Ian P  Linda Bethune. The Comparative In Vitro Activity of FK-037 (Cefoselis), a New Broad-Spectrum Cephalosporin[J]. Clinical Microbiology and Infection, 1995, 1 1: Pages 13-17. DOI:10.1111/j.1469-0691.1995.tb00018.x.