104145-95-1

Basic information

• Product Name: Cefditoren
• Synonyms: (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;Cefditoren-13C-D3
• CAS NO: 104145-95-1
• Molecular Formula: C₁₉H₁₈N₆O₅S₃
• Molecular Weight: 506.586
• Mol File: 104145-95-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.75
• Refractive Index: 1.825
• CAS DataBase Reference: Cefditoren(CAS DataBase Reference)
• NIST Chemistry Reference: Cefditoren(104145-95-1)
• EPA Substance Registry System: Cefditoren(104145-95-1)

Safety Data

• Hazardous Substances Data: 104145-95-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cefditoren is used as an antibiotic for the treatment of mild to moderate infections caused by susceptible strains of microorganisms. It is particularly effective in treating acute bacterial exacerbation of chronic bronchitis, community-acquired pneumonia, pharyngitis/tonsillitis, and uncomplicated skin and skin-structure infections.

InChI:InChI=1/C19H18N6O5S3/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29)/b4-3-,24-12-/t13?,17-/m1/s1

Upstream product

• 155723-02-7 (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 82294-70-0 4-methyl-1,3-thiazole-5-carbaldehyde 
• 957-68-6 7-Aminocephalosporanic acid 
• 1207515-78-3 C₁₃H₁₂N₃O₃S₂^(1-)*Na⁽¹⁺⁾ 
• 64485-88-7 ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate 
• 80756-85-0 (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate 

Downstream Products

• 117467-28-4 cefditoren pivoxil 
• 104146-53-4 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt 
• 104146-16-9 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt 

Related news

PEPT1 involved in the uptake and transepithelial transport of Cefditoren (cas 104145-95-1) in vivo and in vitro08/06/2019

Cefditoren is a third-generation cephalosporin developed by Meiji Seika Kaisha Ltd. Many β-lactam antibiotics are transported by the H+/peptide symporters PEPT1 and PEPT2 that are preferentially expressed in the luminal membrane of the intestine and kidney, respectively. In this study, we emplo...detailed

Formulation evaluation and stability studies of hydrogel tablets containing Cefditoren (cas 104145-95-1) Pivoxil08/05/2019

AimCefditoren Pivoxil hydrogel tablets were prepared to achieve the gastro retentive effect in order to improve its absorption and bioavailability.detailed

Electrochemistry of Cefditoren (cas 104145-95-1) pivoxil and its voltammetric determination08/04/2019

Electrochemical behavior of cefditoren pivoxil (CTP) was studied via experimental electrochemical methods and theoretical calculations performed at B3LYP/6-31+G(d)//AM1 level. Experimental studies were carried out based on an irreversible 4e−/4H+ reduction peak at ca. −0.8 V on hanging mercury d...detailed

Molecular Mechanisms of Biliary Excretion of Cefditoren (cas 104145-95-1) and the Effects of Cefditoren (cas 104145-95-1) on the Expression Levels of Hepatic Transporters08/03/2019

Summary :Cefditoren, a third génération cephalosporin antibiotics, has been used in clinics extensively. Previous results have indicated that cefditoren is excreted into bile as unchanged form. To investigate whether canalicular membrane transporters of hepatocytes were involved in the biliary...detailed

Absorption and bioavailability of Cefditoren (cas 104145-95-1) pivoxil in hydrogels in vitro and in vivo08/02/2019

Superporous gastro-retentive cefditoren pivoxil tablets were prepared to improve the absorption and bioavailability of this drug and evaluated by varying the concentrations of carbopol and sodium carboxymethyl cellulose. The pre-compression and post-compression parameters were within acceptable ...detailed

Efficacy and safety of Cefditoren (cas 104145-95-1) pivoxil for exacerbations of chronic obstructive pulmonary disease: A prospective multicenter interventional study08/01/2019

Oral antibiotic therapy for patients with acute exacerbations of chronic obstructive pulmonary disease (COPD) usually involves an aminopenicillin with clavulanic acid, a macrolide, or a quinolone. To date, however, the clinical efficacy and safety of the oral cephalosporin cefditoren pivoxil has...detailed

Relevant articles and documents

Preparation method of cefditoren pivoxil

The invention relates to a preparation method of cefditoren pivoxil. The preparation method comprises the following steps: 7-aminocephalosporanic acid(ACA) is taken as a starting material and subjected to a series of reactions such as iodination and the like after silylation protection to generate parent nucleus for cefditoren, namely 7-amino-3-[(Z)-2-(4-methyl-5-thiazolyl)ethenyl]-3-cephem-4-carboxylic acid (7-ATCA); the compound 7-ATCA firstly reacts with sodium iso-octoate to form sodium salt and then reacts with ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate to generate a compound 2,namely cefditoren sodium, under the catalysis of immobilized penicillin acylase; and then the cefditoren sodium reacts with iodomethyl pivalate to obtain a target product, namely cefditoren pivoxil.The preparation method is mild in reaction conditions, environmentally-friendly, high in conversion rate, simple in process, high in content of cis isomers, easy to enlarge and suitable for industrialproduction.

Preparation method of cefditoren pivoxil

The invention discloses a preparation method of an important antibiotic cefditoren pivoxil. The preparation method comprises that 7-ATCA as a raw material is bonded to an AE active ester under base catalysis so that cefditoren acid is obtained, the cefditoren acid and sodium bicarbonate undergo a reaction to produce a salt, and the salt and cefditoren pivoxil undergo a replacement reaction under alkaline conditions to produce 2, 2-dimethylpropionyloxy(6R, 7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-[(Z)-2-(4-methyl-1, 3-thiazolyl-5-yl)vinyl]-8-oxo-5-thia-1-azabicyalo[4. 2. 0]octyl-2-ene-2-formate. The preparation method has the advantages of low cost, simple operation, high purity, use of cheap and easily available raw materials, industrial production feasibility and small pollution.

Method for preparing cefditoren pivoxil cephalosporins

The invention discloses a method for preparing cefditoren pivoxil cephalosporins.The method comprises the following steps that 1, on the presence of TMEDA and sodium phosphate, 7-ATCA and MAEM are subjected to a contact reaction in THF, and a mixture containing cefditore is obtained, and the contact reaction temperature ranges from 0 to 25 DEG C; 2, the temperature is kept, TEA is added to the mixture containing cefditore obtained in the step 1, then iodomethyl pivalate is added to the mixture to be stirred for reacting, the product is poured into water after the reaction is finished, a saturated ammonium chloride solution is added, the pH is adjusted to be 5 to 5.3, filtering is carried out, and a filter cake obtained through filtering is recrystallized in methyl alcohol to obtain cefditoren pivoxil cephalosporins.According to the method, separation treatment is not needed in the intermediate steps, one-pot operation is easy, cost is reduced, the yield is high, the number of by-products is small, aftertreatment is easy, and the method is especially suitable for industrial popularization.

DEPLETION OF E-ISOMERS IN PREPARATION OF Z-ENRICHED 3-(2-SUBSTITUTED VINYL) CEPHALOSPORINS

The present invention relates to depleting E-isomers of 3-(2-substituted vinyl) cephalosporins from a Z/E mixture of the same by selective crystallization techniques. The present invention to Z-enriched compounds comprising less than 5 % E-isomer.

Process for the preparation of cefditoren using the thioester of thiazolylacetic acid

The present invention provides a process for the preparation of Cefditoren of formula (I) which comprises acylating 7-amino-cephem carboxylic acids of the general formula (IV), where R3 is hydrogen or trimethylsilyl with thioester derivatives of the formula (II), where R1 represents C1-C4 alkyl or phenyl in an organic solvent in the presence of an organic base at a temperature in the range of ?10 ° C. to 30 ° C.

A NEW PROCESS FOR THE PREPARATION OF CEFDITOREN USING THE THIOESTER OF THIAZOLYLACETIC ACID

The present invention provides a process for the preparation of Cefditoren of formula (I) which comprises acylating 7-amino-cephem carboxylic acids of the general formula (IV), where R3 is hydrogen or trimethylsilyl with thioester derivatives of the formula (II), where R1 represents C1 - C4 alkyl or phenyl in an organic solvent in the presence of an organic base at a temperature in the range of -10 °C to 30 °C.

Crystalline substance of cefditoren pivoxyl and the production of the same

As a novel substance is provided such a new, crystalline substance of Cefditoren povoxyl which has a high purity and an enhanced thermal stability on storage. This crystalline Cefditoren pivoxyl may be prepared by a process comprising a step of dissolving amorphous substance of Cefditoren pivoxyl in an anhydrous, first organic solvent capable of dissolving said amorphous substance well therein, and steps of replacing the first organic solvent component of the resulting solution by an anhydrous alkanol of 1 to 5 carbon atoms as a second organic solvent, in such a manner that the firstly prepared solution of Cefditoren pivoxyl in the first organic solvent is mixed with a volume of the alkanol and then is concentrated below 15° C. under reduced pressure, and so on. Thereby, the process proceeds so as to produce a solution containing 50 mg/ml to 250 mg/ml of Cefditoren pivoxyl dissolved in the alkanol alone. From the latter solution, crystals of Cefditoren pivoxyl are induced to deposit by addition of water at a temperature of 0-10° C. The resulting admixture of the concentrated solution of Cefditoren pivoxyl in alkanol with added water and the deposited Cefditoren pivoxyl is then agitated 10° C. or below, to effect a complete crystallization of Cefditoren pivoxyl.