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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 |
| 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 | | pka | 8.08±0.60(Predicted) | | color | Off-White to Pale Yellow | | Merck | 14,1921 | | CAS DataBase Reference | 117467-28-4(CAS DataBase Reference) |
| 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. | | 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) | | Uses | Cefditoren Pivoxil is an antibacterial and is a third generation cephalosporin. | | 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. |
| Cefditoren pivoxil Preparation Products And Raw materials |
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