Product Name: Cefcapene pivoxil
Synonyms: CEFCAPENE PIVOXIL;(6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, (2,2-Dimethyl-1-oxopropoxy)methyl Ester;Fumax;S-1108;Cefcapene Piroxil;Flumax;Cefcapene Pivoxil See C242555;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aMinocarbonyl)oxy]Methyl]-7-[[(2Z)-2-(2-aMino-4-thiazolyl)-1-oxo-2-penten-1-yl]aMino]-8-oxo-,(2,2-diMethyl-1-oxopropoxy)Methyl ester, (6R,7R)-
CAS: 105889-45-0
MF: C23H29N5O8S2
MW: 567.64
EINECS: 1806241-263-5
Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles;Metabolites & Impurities;Sulfur & Selenium Compounds;-;Pharmaceutical intermediate
Mol File: 105889-45-0.mol
Cefcapene pivoxil Structure
Cefcapene pivoxil Chemical Properties
Melting point 158-164°C
Boiling point 888.4±65.0 °C(Predicted)
density 1.47±0.1 g/cm3(Predicted)
pka 11.33±0.60(Predicted)
Safety Information
MSDS Information
Cefcapene pivoxil Usage And Synthesis
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.
Chemical Properties Off-White Solid
Originator Shionogi (Japan)
Uses Antibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, cefcapene
Brand name Flomox
China
