Cefcapene pivoxil

Base Information

• Chemical Name: Cefcapene pivoxil
• CAS No.: 105889-45-0
• Molecular Formula: C23H29N5O8S2
• Molecular Weight: 567.644
• Hs Code.: 2942000000
• UNII: 8I8MJ56XFQ
• DSSTox Substance ID: DTXSID7049134
• Nikkaji Number: J475.209K
• Wikidata: Q27270575
• NCI Thesaurus Code: C98218
• ChEMBL ID: CHEMBL2431072
• Mol file: 105889-45-0.mol

Synonyms:S 1108;S-1108

Chemical Property of Cefcapene pivoxil

Chemical Property:

• Vapor Pressure: 3.51E-32mmHg at 25°C
• Melting Point: 158-164°C
• Refractive Index: 1.638
• Boiling Point: 888.4 °C at 760 mmHg
• PKA: 11.33±0.60(Predicted)
• Flash Point: 491.1 °C
• PSA: 246.78000
• Density: 1.47 g/cm³
• LogP: 2.96830
• Solubility.: DMSO, Water( warm)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 13
• Exact Mass: 567.14575525
• Heavy Atom Count: 38
• Complexity: 1060

Purity/Quality:

99% ^*data from raw suppliers

CefcapenePivoxil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C
• Isomeric SMILES: CC/C=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C
• Description: Flomox was launched in Japan as an orally active cephalosporin for respiratory and urinary tract infections, heptatic infections, ophthalmological and otorhinolarynological infections, skinkoft tissue infections, and for use in gynacology, dentistry and oral surgery. It can be prepared by condesation of 2(Z)-(2-(t-butoxycarbonylamino) thiazol-4-yl)-2-pentenoic acid with 7-amino-3-(carbanoyloxymethyl)- 3-cephem-4-carboxylic acid pivaloyl methyl ester followed by deprotection. Flomox is highly active against a wide variety of Gram-positive and Gram-negative bacteria, except for several strains such as Pseudomonas aeruginosa and enterococci, by acting as a cell wall synthesis inhibitor (β-lactamase stability against TEM-1 type β-lactamases) and is more effective than cefaclor and cefdinir. Absorption is improved by the pivaloyloxymethyl ester group which is easily lost by deesterification during GI absorption to produce the biologically active form. The pivalic acid generated quickly conjugates with carnitine and is excreted in the urine. The drop in plasma levels of carnitine was dose dependent and returned to normal levels upon termination of treatment.
• Uses: Antibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, Cefcapene. Antibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, cefcapene

Technology Process of Cefcapene pivoxil

There total 12 articles about Cefcapene pivoxil 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: 73.0%

((6R,7R)-3-((aminocarbonyl)oxy)methyl-7-((Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino)-8-oxo-5-thio-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid(2,2-dimethyloxypropoxymethyl)ester (105889-80-3) → cefcapene pivoxil (105889-45-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.7164/antibiotics.47.466

Reference yield:

7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (105890-10-6) → cefcapene pivoxil (105889-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 51.1 percent / K₂CO₃ / dimethylformamide / 1.5 h / -40 °C

2: 73 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

With potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.466

Reference yield:

iodomethyl pivaloate (53064-79-2) → cefcapene pivoxil (105889-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 51.1 percent / K₂CO₃ / dimethylformamide / 1.5 h / -40 °C

2: 73 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

With potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.466

upstream raw materials:

((6R,7R)-3-((aminocarbonyl)oxy)methyl-7-((Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino)-8-oxo-5-thio-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid(2,2-dimethyloxypropoxymethyl)ester

iodomethyl pivaloate

7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTIC". Page/Page column 11. . Retrieved 2009/01/23.