ChemicalBook > CAS DataBase List > Cefditoren pivoxil

Cefditoren pivoxil

Product Name
Cefditoren pivoxil
CAS No.
117467-28-4
Chemical Name
Cefditoren pivoxil
Synonyms
CEFDITOREN;Spectracef;CEFDITORIN PIVOXIL;Meiac;MEIACT;ME-1207;toubaotuolunzhi;toubaotuolkunzhi;ceditoren pivoxil;Cefditoren Pivoxi
CBNumber
CB7377697
Molecular Formula
C25H28N6O7S3
Formula Weight
620.72
MOL File
117467-28-4.mol
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Cefditoren pivoxil Property

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)
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Safety

RTECS 
XI0367800
HS Code 
2941.90.3000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
C2856
Product name
Cefditoren Pivoxil
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$248
Updated
2024/03/01
Cayman Chemical
Product number
30315
Product name
Cefditoren Pivoxil
Packaging
5mg
Price
$68
Updated
2024/03/01
Cayman Chemical
Product number
30315
Product name
Cefditoren Pivoxil
Packaging
10mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
30315
Product name
Cefditoren Pivoxil
Packaging
50mg
Price
$201
Updated
2024/03/01
Cayman Chemical
Product number
30315
Product name
Cefditoren Pivoxil
Packaging
100mg
Price
$268
Updated
2024/03/01
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Cefditoren pivoxil Chemical Properties,Usage,Production

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

Raw materials

Preparation Products

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Cefditoren pivoxil Suppliers

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View Lastest Price from Cefditoren pivoxil manufacturers

Guangzhou Tosun Pharmaceutical Ltd
Product
Cefditoren Pivoxil Impurity 25
Price
US $0.00-0.00/mg
Min. Order
5mg
Purity
95%+
Supply Ability
1000mg
Release date
2024-12-18
Guangzhou Tosun Pharmaceutical Ltd
Product
Cefditoren Pivoxil 117467-28-4
Price
US $0.00-0.00/mg
Min. Order
5mg
Purity
95%+
Supply Ability
1000mg
Release date
2024-12-18
Hebei Zhanyao Biotechnology Co. Ltd
Product
Cefditoren pivoxil 117467-28-4
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-11-12

117467-28-4, Cefditoren pivoxilRelated Search:

Ceftezole (6R,7R) Cefotetan disodium Flomoxef Sulbactam pivoxil Cefditoren Cefazedone Cefoxitin Ceftezole sodium Cefoxitin sodium Cefovecin Sodium Methyl N,N-dimethylaminoacrylate (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 7-AVCA Cefditoren pivoxil Cefetamet pivoxyl Cefdinir 4-Methyl-5-vinylthiazole

  • (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
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  • CEFDITOREN PIVALOYLOXYMETHYL ESTER
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  • Cefditoren Pivoxil (350 mg)
  • 2,2-Dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • CEFDITORIN PIVOXIL
  • (6R,7R)-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(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- (2,2-dimethyl-1-oxopropoxy)methyl ester
  • (2,2-)(methoxyimino)acetyl)amino)-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo
  • toubaotuolkunzhi
  • CEFDITOREN PIVOXYL;CEFDITOREN PIVALOYLOXYMETHYL ESTER;ME 1207
  • Cefditoren Pivoxil &gt
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R,7R)-
  • (6R,7R)-(pivaloyloxy)methyl7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((Z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
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  • 4-Dihydroxy-5-methoxybenzoic acid
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  • Cefthoram pipivoxil
  • Ceftoram pipivoxil
  • Cefditoren pivoxil, 10 mM in DMSO
  • 117467-28-4
  • C25H28N6O7S3
  • CYMBALTA
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • Cefditoren
  • 117467-28-4