Cefcapene pivoxil

Cefcapene pivoxil Basic information
Product Name:Cefcapene pivoxil
Synonyms:(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;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)
solubility DMSO, Water( warm)
form Solid
pka11.33±0.60(Predicted)
color Off-White
Safety Information
MSDS Information
Cefcapene pivoxil Usage And Synthesis
DescriptionFlomox 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 PropertiesOff-White Solid
OriginatorShionogi (Japan)
UsesAntibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, Cefcapene.
Brand nameFlomox
Cefcapene pivoxil Preparation Products And Raw materials
Raw materialsIodomethane-->Trifluoroacetic acid-->Phosphoric acid-->Methanesulfonyl chloride-->Anisole
Cefetamet pivoxyl Methyl CEFCAPENE PIVOXIL-D9 CEFCAPENE PIVOXIL HCL Cefamandole 2-Mercaptobenzothiazole Fosthiazate Parathion-methyl Sodium cefamandole Cefcapene Pivoxil Hydrochlrode JP METHYL-2-N-ACETYL CROTANOATE Cefpodoxime proxetil cefcapene pivoxil hydrochloride Kresoxim-methyl Thiophanate-methyl 2-(2-Aminothiazol-4-yl)glyoxylic acid Methyl N,N-dimethylaminoacrylate METSULFURON METHYL

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