105889-45-0

Basic information

• 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 NO: 105889-45-0
• Molecular Formula: C₂₃H₂₉N₅O₈S₂
• Molecular Weight: 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
• Article Data: 3

Chemical Properties

• Melting Point: 158-164°C
• Boiling Point: 888.4 °C at 760 mmHg
• Flash Point: 491.1 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 3.51E-32mmHg at 25°C
• Refractive Index: 1.638
• Solubility: DMSO, Water( warm)
• PKA: 11.33±0.60(Predicted)
• CAS DataBase Reference: Cefcapene pivoxil(CAS DataBase Reference)
• NIST Chemistry Reference: Cefcapene pivoxil(105889-45-0)
• EPA Substance Registry System: Cefcapene pivoxil(105889-45-0)

Safety Data

• Hazardous Substances Data: 105889-45-0(Hazardous Substances Data)

Usage

Description

Cefcapene pivoxil, marketed under the brand name Flomox, is an orally absorbed cephalosporin antibiotic. It is an ester prodrug of the active free acid metabolite, cefcapene, and is highly effective against a wide range of Gram-positive and Gram-negative bacteria, except for certain strains like Pseudomonas aeruginosa and enterococci. The drug works by inhibiting cell wall synthesis and possesses β-lactamase stability against TEM-1 type β-lactamases. Its absorption is enhanced by the pivaloyloxymethyl ester group, which is easily lost by deesterification during gastrointestinal absorption, producing the biologically active form. Cefcapene pivoxil is an off-white solid and was launched in Japan for various medical applications.

Uses

Used in Antibacterial Applications:
Cefcapene pivoxil is used as an antibacterial agent for treating a wide range of bacterial infections, including respiratory and urinary tract infections, hepatic infections, ophthalmological and otorhinolaryngological infections, skin and soft tissue infections, and infections in gynecology, dentistry, and oral surgery.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Cefcapene pivoxil is used as an orally active cephalosporin antibiotic for the development of medications to combat bacterial infections. Its high activity against various bacteria and improved absorption make it a promising candidate for antibiotic formulations.
Used in Medicinal Chemistry:
Cefcapene pivoxil is utilized in medicinal chemistry for the synthesis and study of cephalosporin-based antibiotics. Its unique properties, such as β-lactamase stability and enhanced absorption, make it an important compound for research and development in the field of antibiotic discovery.

Originator

Shionogi (Japan)

InChI:InChI=1/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6+/t14-,18-/m1/s1

Upstream product

• 957-68-6 7-Aminocephalosporanic acid 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 153012-37-4 [(6R,7R)-7-[(2Z)-2-(2-{[(tert-butoxy)carbonyl]amino}-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate salt 
• 1360188-88-0 C₂₁H₂₄N₄O₆S₂ 
• 153012-25-0 (6R,7R)-7-((2Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino-3-hydroxymethyl-3-cephem-4-carboxylic acid 
• 86978-24-7 (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid 
• 105890-09-3 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate 
• 105890-10-6 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid 
• 53064-79-2 iodomethyl pivaloate 
• 105889-80-3 ((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 

Related news

Study of the absorption of Cefcapene pivoxil (cas 105889-45-0) in patients with infectious disease and soft stool or diarrhea07/20/2019

Cefcapene pivoxil hydrochloride (CFPN-PI), an ester cephem antibiotic, was orally given at a dose of 100mg three times daily in patients with infection and soft stool or diarrhea, and its absorption was determined using the recovery ratio of 12-h urine pooled after the initial administration as ...detailed

Pharmacokinetics of Cefcapene pivoxil (cas 105889-45-0) and AS-924 in gastrectomized patients07/18/2019

To investigate the effects of gastrectomy on the absorption of drugs, the blood concentrations of the active moieties, cefcapene (CCAP) and ceftizoxime (CTIZ), were determined in 36 gastrectomized patients after oral administration of cefcapene pivoxil (CCAP-PI) and AS-924, prodrug type cephem a...detailed

Relevant articles and documents

A practical synthesis of cefcapene pivoxil

Cefcapene pivoxil monohydrochloride monohydrate, a broad spectrum third-generation cephalosporin for oral administration, was prepared by reacting three centers of 7-amino-3-(hydroxymethyl)cephalosporinic acid (7-HACA), derived from 7-aminocephalosporanic acid. The coupling of 7-HACA and (Z)-2-[2-(Boc-amino)thiazol-4-yl]pent-2-enoic acid, followed by carbamylation with chlorosulfonyl isocyanate, and precipitation with diisopropylamine gave the key intermediate, in which thiazole side chain and carbamoyl group had been introduced into the 7-amino and 3-hydroxymethyl groups of 7-HACA, respectively, in a continuous procedure. Afterwards, the intermediate was esterified with pivaloyloxymethyl iodide to complete the modification of the C4 carboxy group affording Boc-cefcapene pivoxil, from which the desired product was finally obtained by an economical Boc removal and successive formation of the hydrochloride in 36% overall yield on a decagram scale. This synthesis promises an easy entry to cefcapene pivoxil monohydrochloride monohydrate with convenient manipulation, simple isolation, and good yields; it is of potential value for production on an industrial scale. Georg Thieme Verlag Stuttgart · New York.

Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoyl-amino]-3-cephems with C-3 substitutions

Synthesis and biological activity of a series of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoylamino]-3-cephem-4-carboxylic acids with C-3 substitutions and their pivaloyloxymethyl esters are described. These acid compounds exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. Pivaloyloxymethyl esters of selected compounds in this series were found to be well absorbed from small intestine in mice. Pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoylamino]-3- carbamoyloxymethyl-3-cephem-4-carboxyiate hydrochloride hydrate (S-1108) was finally selected as the candidate for clinical evaluation.