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Cefditoren pivoxil

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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
Mol File:
117467-28-4.mol
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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. 
-20?C Freezer
pka
8.08±0.60(Predicted)
Merck 
14,1921
CAS DataBase Reference
117467-28-4(CAS DataBase Reference)
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Safety Information

RTECS 
XI0367800
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Cefditoren pivoxil Usage And Synthesis

Description

Cefditoren 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.

Chemical Properties

Off-White Powder

Originator

Meiji Seika (Japan)

Uses

An antibacterial. Third generation cephalosporin

Uses

antidepressant

Definition

ChEBI: The pivaloyloxymethyl ester prodrug of cefditoren.

Manufacturing Process

A 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 name

Meiact

Therapeutic Function

Antibiotic

Antimicrobial activity

It 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.

Pharmacokinetics

Oral 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 Use

It has been advocated for community-acquired upper and lower respiratory tract infections and skin infections.

Side effects

In common with other pivoxil esters it may cause carnitine deficiency. Other side effects are those common to cephalosporins, mainly gastrointestinal disturbance.

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