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HomeProduct name listCefditoren pivoxil

Cefditoren pivoxil

  • CAS NO.:117467-28-4
  • Empirical Formula: C25H28N6O7S3
  • Molecular Weight: 620.72
  • MDL number: MFCD00933166
  • EINECS: 688-157-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 21:40:10
Cefditoren pivoxil Structural

What is Cefditoren pivoxil?

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.

Description

Cefditoren 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 properties

Off-White Powder

Originator

Meiji Seika (Japan)

The Uses of Cefditoren pivoxil

Cefditoren Pivoxil is an antibacterial and is a third generation cephalosporin.

The Uses of Cefditoren pivoxil

An antibacterial. Third generation cephalosporin

The Uses of Cefditoren pivoxil

antidepressant

What are the applications of Application

Cefditoren Pivaloyloxymethyl Ester is a third generation cephalosporin and β-Lactam antibacterial

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.

Properties of Cefditoren pivoxil

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
pka 8.08±0.60(Predicted)
color  Off-White to Pale Yellow
Merck  14,1921
CAS DataBase Reference 117467-28-4(CAS DataBase Reference)

Safety information for Cefditoren pivoxil

Computed Descriptors for Cefditoren pivoxil

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Hetero Drugs Limited

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Suvan LifeSciences (formerly Sansh Biotech Pvt Ltd)

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Covalent Laboratories Private Limited (Virchow Group)

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Akums Lifesciences Ltd

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SETV ASRV LLP

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Phone:+91-9731133411
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product: CEFDITOREN PIVOXIL 95-99%
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