Cefditoren pivoxil

Cefditoren pivoxil Basic information
Product Name:Cefditoren pivoxil
Synonyms:(6r-(3(z),6-alpha,7-beta-(z)))-dimethyl-1-oxopropoxy)methyleste;MEIACT;ME-1207;(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Pivaloyloxymethyl Ester;Meiac;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [6R-[3(Z),6α,7β(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R,7R)-;ceditoren pivoxil
CAS:117467-28-4
MF:C25H28N6O7S3
MW:620.72
EINECS:688-157-7
Product Categories:CYMBALTA;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Cefditoren;117467-28-4
Mol File:117467-28-4.mol
Cefditoren pivoxil Structure
Cefditoren pivoxil Chemical Properties
Melting point 207-209°C
alpha D20 -48.5° (c = 0.5 in methanol)
density 1.55±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly, Heated)
form Solid
pka8.08±0.60(Predicted)
color Off-White to Pale Yellow
Merck 14,1921
CAS DataBase Reference117467-28-4(CAS DataBase Reference)
Safety Information
RTECS XI0367800
HS Code 2941.90.3000
MSDS Information
Cefditoren pivoxil Usage And Synthesis
DescriptionCefditoren pivoxil is an orally active third generation cephalosporin introduced in Japan as a treatment for a broad range of bacterial infections including dermatological and other community acquired infections. Cefditoren pivoxil is reported to have a broad spectrum of activity against both Gram-positive and Gramnegative bacteria, more potent than many other existing agents of its class. In particular, it shows the highest therapeutic activity against S. pneumoniae and S. marcescens infections. It exhibits resistance to β-lactamase hydrolysis typical of third generation cephalosporins. As a prodrug of cefditoren, it is readily absorbed through GI tract and has low toxicity and side effects.
DescriptionCefditoren pivoxil is an orally bioavailable prodrug form of the broad-spectrum cephalosporin antibiotic cefditoren. Cefditoren pivoxil is hydrolyzed by intestinal wall esterases to form cefditoren. Cefditoren pivoxil is effective against systemic S. aureus, E. coli, K. pneumoniae, P. mirabilis, or S. marcescens infections in mice with ED50 values of 10, 2.5, 11, 4.4, and 11 mg/kg, respectively. Formulations containing cefditoren pivoxil were previously used in the treatment of acute bacterial exacerbations of chronic bronchitis and community-acquired pneumonia.
Chemical PropertiesOff-White Powder
OriginatorMeiji Seika (Japan)
UsesCefditoren Pivoxil is an antibacterial and is a third generation cephalosporin.
UsesAn antibacterial. Third generation cephalosporin
Usesantidepressant
DefinitionChEBI: The pivaloyloxymethyl ester prodrug of cefditoren.
Manufacturing ProcessA mixture of THF (250 ml) and water (150 ml) was stirred under inert atmosphere. At 0°-1°C, 7-amino-3-[(Z)-2-(methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid (25.0 g) and 2-mercapto-5-phenyl-1,3,4- oxadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino acetate (33.3 g) were added. Triethylamine (10.5 g) was slowly added to reaction by maintaining the pH between 7.5 to 8.5. The reaction was monitored by HPLC. After 4-5 hrs., the reaction mixture was extracted by methylene chloride. The aqueous layer is subjected for charcoal (0.125 g) treatment. Ethylacetate was added to the filtrate and the solution was acidified with diluted HCl at 10°C to pH 3.0. The solid separated was filtered, washed with water and ethylacetate and then dried under vacuum at 40-45°C to get 3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-7- [(Z)-(2-aminothiazolyl-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4- carboxylic acid (Cefditoren acid), 35.0 g (yield 90%), HPLC (purity)=96-98%.
In practice it is often used as Cefditoren pivoxil.
Brand nameMeiact
Therapeutic FunctionAntibiotic
Antimicrobial activityIt exhibits good activity against staphylococci, streptococci (but not enterococci), H. influenzae and M. catarrhalis, including β-lactamase-producing strains. Isolates of Str. pneumoniae exhibiting reduced susceptibility to penicillin are less susceptible (MIC 0.125–2 mg/L). Most enterobacteria, including many Enterobacter, Citrobacter, Serratia and Proteus spp., are susceptible. It is not active against Ps. aeruginosa, Sten. maltophilia or atypical respiratory pathogens such as Chlamydophila pneumoniae and M. pneumoniae. It is stable to staphylococcal and common enterobacterial β-lactamases.
PharmacokineticsOral absorption: c. 70%
Cmax 200 mg oral: c. 1.8 mg/L after 1.5–3 h
Plasma half-life: 0.8–1.3 h
Volume of distribution: 9.3 L
Plasma protein binding: 88%
After oral administration the pivaloyl ester is rapidly cleaved by esterases in the gut wall. Ingestion with food improves the bioavailability. Plasma concentrations are raised in elderly patients. There is no accumulation on repeated dosing.
It is excreted unchanged in the urine with a half-life of around 1.5 h, achieving a concentration of 150–200 mg/L within 4 h. Dosage adjustment is recommended in patients with deteriorating renal function.





Clinical UseIt has been advocated for community-acquired upper and lower respiratory tract infections and skin infections.
Side effectsIn common with other pivoxil esters it may cause carnitine deficiency. Other side effects are those common to cephalosporins, mainly gastrointestinal disturbance.
Cefditoren pivoxil Preparation Products And Raw materials
Raw materialsTriethylamine-->5-(4-METHYLPHENYL)-1,3,4-OXADIAZOLE-2-THIOL
Flomoxef Cefotetan disodium (6R,7R) Sulbactam pivoxil Cefditoren Cefetamet pivoxyl 7-AVCA CEFDITOREN PIVOXIL CEPHALOSPORINS, CEFDITOREN PIVOXIL CEPHALOSPORINS METHYL-2-N-ACETYL CROTANOATE (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-Methyl-5-vinylthiazole Cefditoren Pivoxil oral,Cefditoren Pivoxil oral Cefditoren-D3 Sodium Salt Cefditoren pivoxil Cefdinir 4-methylthiazole-5-carboxaldehyde (intermediate of cefditoren pivoxil),4-methylthiazole-5-carboxaldehyde (intermediate of cefditoren pivoxil) Methyl N,N-dimethylaminoacrylate Cefditoren pivoxil JP,Cefditoren pivoxil JP

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