117467-28-4 Usage
Description
Different sources of media describe the Description of 117467-28-4 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 117467-28-4 differently. You can refer to the following data:
1. Cefditoren Pivoxil is an antibacterial and is a third generation cephalosporin.
2. An antibacterial. Third generation cephalosporin
3. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 117467-28-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,4,6 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 117467-28:
(8*1)+(7*1)+(6*7)+(5*4)+(4*6)+(3*7)+(2*2)+(1*8)=134
134 % 10 = 4
So 117467-28-4 is a valid CAS Registry Number.
InChI:InChI=1/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/t17-,21-/m1/s1
117467-28-4Relevant articles and documents
Preparation method of cefdiaxone pivoxil
-
, (2020/06/05)
The invention relates to a preparation method of Cefditoren Pivoxil. The preparation method comprises steps as follows: 7-ACA (3-acetyloxymethyl-5-thio-7-amino-8-oxy-1-nitrogen heterobicyclic octyl-2-ene-2 carboxylic acid) is taken as a starting raw material and is subjected to iodination and Wittig reaction after silanization protection, and a Cefditoren parent nucleus 7-ATCA (7-amino-3-[(Z)-2-(4-methyl-5-thiazole) vinyl]-3-cephem-4-carboxylic acid) is generated; after amino protection of aminothiazole ethyl gallate, a compound 2 is produced from 7-ATCA under catalysis of AlMe3; the compound2 is subjected to an esterification reaction with iodomethyl pivalate under actions of a phase transfer catalyst and an acid adsorbent, the amino protection is removed, and a target product CefditorenPivoxil is obtained. According to the preparation method, reaction conditions are mild, product purity and yield are high, the process is stable, amplification is easy, and the method is applicable to industrial production.
Preparation method of cefditoren pivoxil
-
, (2019/02/27)
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.
A spore proper logical sequence of the ester preparation method
-
Paragraph 0035; 0038; 0039; 0046; 0054; 0056; 0064, (2018/09/02)
The invention belongs to the technical field of medicines and particularly relates to a preparation method of cefditoren pivoxil. The preparation method particularly includes following steps: (1) carrying out a reaction between cefditoren mother nucleus 7ATCA and AE-activated ester with dichloromethane as a solvent under an alkaline condition at 0-5 DEG C; (2) performing extraction with pure water and adding a sodium iso-octoate/acetone solution to obtain cefditoren sodium; (3) carrying out a reaction between the cefditoren sodium and iodomethyl pivalate under the alkaline condition at -40 DEG C to obtain a cefditoren pivoxil solution; (4) adding pure water to separate out a crystal to obtain a crude product of the cefditoren pivoxil. The technical scheme also comprises steps of dissolving the crude product of the cefditoren pivoxil in a mixed solution including dichloromethane and anhydrous ethanol, washing the material solution with a 1% sodium bicarbonate solution and pure water, collecting an organic phase, and performing a pressure-reducing evaporate-drying process to obtain the cefditoren pivoxil being higher than 99% in purity and less in impurities. The preparation method is simple in operation, is easy to control, is high in yield, allows the raw material to be obtained easily and is suitable for industrialized large-scale production.
