Ceftibuten

Product Name: Ceftibuten
CAS No.: 97519-39-6
Chemical Name: Ceftibuten
Synonyms: cephem;Ceftibutene;s7432;7432S;CS-1355;CEFTIBUTEN;Cedax：Isocef;cis-ceftibutin;cis-Ceftibuten;antibiotic7432s
CBNumber: CB7299436
Molecular Formula: C15H14N4O6S2
Formula Weight: 410.42
MOL File: 97519-39-6.mol

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Ceftibuten Property

Boiling point:: 966℃
Density: 1.75±0.1 g/cm3(Predicted)
RTECS: XI0367220
Flash point:: >110°(230°F)
storage temp.: Keep in dark place,Sealed in dry,2-8°C
solubility: Soluble in aqueous solutions. Also soluble in DMSO
form: powder
pka: 2.99±0.50(Predicted)
color: white to beige

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H332Harmful if inhaled

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

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

P271Use only outdoors or in a well-ventilated area.

P285In case of inadequate ventilation wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0037
Product name: Ceftibuten hydrate
Purity: ≥98% (HPLC)
Packaging: 10mg
Price: $102
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0037
Product name: Ceftibuten hydrate
Purity: ≥98% (HPLC)
Packaging: 50mg
Price: $394
Updated: 2024/03/01

Alfa Aesar

Product number: J66807
Product name: Ceftibuten, 95%
Packaging: 10mg
Price: $112
Updated: 2021/12/16

Alfa Aesar

Product number: J66807
Product name: Ceftibuten, 95%
Packaging: 50mg
Price: $312
Updated: 2021/12/16

ApexBio Technology

Product number: B3442
Product name: Ceftibuten
Packaging: 10mg
Price: $54
Updated: 2021/12/16

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Ceftibuten Chemical Properties,Usage,Production

Description

Ceftibuten is a new, once daily, orally active cephalosporin introduced as a treatment of Gram-negative bacteria-related urinarylrespiratory tract and gynecological infections. In vitro studies of 359 strains of Gram-negative bacteria demonstrated that ceftibuten was superior to cefaclor and as active or slightly more active than cefixime and cefteram.

Originator

Shionogi (Japan)

Uses

anorexic, antidepressant, inhibitor of 5HT, norepinephrine & dopamine uptake

Definition

ChEBI: A third-generation cephalosporin antibiotic with a [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino substituent at the 7 position of the cephem skeleton. An orally-administered agent, ceftibuten is used as the dihydrate to tre t urinary-tract and respiratory-tract infections.

Manufacturing Process

The 1st method of synthesis
The 8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-1-ene-2- carboxylic acid benzhydryl ester is reacted with phosphorus pentachloride/pyridine reagent in methylene dichloride, and the reaction mixture is thereafter cooled to -35°C and treated with methanol to produce hydrochloride of 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid benzhydryl ester. This hydrochloride is reacted with 4-(3- aminothiophen-2-yl)-5-oxohex-3-enoic acid 3-methylbut-2-enyl ester. Then 7- [2-(2-benzoylamino-thiazol-5-yl)(3-tert-butyl-4,4-dimethylpent-2- enoxycarbonyl)-pent-2-enoylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2- ene-2-carboxylic acid synthesized is reacted with aluminum chloride in anisole and diluted hydrochloric acid and then with dimethylmalonate to give 5-thia- 1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-2-(2-amino-4- thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6R,7R)- (Ceftibuten).
The 2st method of synthesis
Formulation of the diphenylmethyl thiazoleacetate with ethyl formate leads to 2-(2-aminothiazol-5-yl)-3-hydroxyacrylic acid benzhydryl ester. Condensation of 2-(2-aminothiazol-5-yl)-3-hydroxyacrylic acid benzhydryl ester with the phosphorane from benzyl 2-triphenylphosphonium acetate leads to the 2-(2- aminothiazol-5-ylmethylene)succinic acid 1-benzhydryl ester 4-benzyl ester. Exposure of this ester to trifluoroacetic acid selectively cleaves the diphenylmethyl group over the benzyl ester to give 2-(2-aminothiazol-5- ylmethylene)succinic acid 4-benzyl ester. Condensation of the acid with free amino group in the desmethyl cephalosporin affords the amide of 7-[3-(2- aminothiazol-5-yl)-2-benzoylcarbonylmethylacryloylamino)-8-oxo-5-thia-1- azabicyclo[4.2.1]oct-2-ene-2-carboxylic acid benzyl ester. The remaining benzyl ester protecting groups are removed by means of aluminum chloride to afford 7-[3-(2-aminothiazol-5-yl)-2-benzoylcarbonylmethylacryloylamino)-8- oxo-5-thia-1-azabicyclo[4.2.1]oct-2-ene-2-carboxylic acid or ceftibuten

brand name

Cedax (Schering);Seftem.

Therapeutic Function

Antibiotic

Antimicrobial activity

A semisynthetic cephalosporin formulated as the dihydrate for oral administration.
It exhibits good activity against many Gram-negative bacilli, but its activity against Gram-positive cocci is very poor. It is stable to hydrolysis by the common plasmid-mediated β-lactamases, but not derepressed chromosomal enzymes .
It is rapidly and almost completely absorbed by mouth and is excreted in the urine with a half-life of 1.5–3 h. An oral dose of 400 mg achieves a peak plasma concentration of around 15 mg/L. Binding to plasma proteins is 65–77%.
Side effects mostly consist of mild gastrointestinal symptoms and mild liver function test changes. Clinical trials have mainly been conducted in urinary tract and respiratory tract infections which, despite the poor in-vitro activity against Str. pneumoniae, have shown ceftibuten to be as efficacious as comparator agents.

General Description

Chemical structure: ?-lactam

Biochem/physiol Actions

Ceftibuten is a third generation cephalosporin antibiotic

Pharmacokinetics

Ceftibuten is highly (75–90%) absorbed on oral administration, but this is decreased significantly by food. Being lipophilic and acidic, it is significantly (65%) serum protein bound. Some isomerization of the geometry of the olefinic linkage appears to take place in vivo before excretion.

Clinical Use

Ceftibuten (Cedax) is a recently introduced, chemicallynovel analog of the oximino cephalosporins in which anolefinic methylene group (C＝CHCH_2-) with Z stereochemistryhas replaced the syn oximino (CBNO-) group.
This isosteric replacement yields a compound that retainsresistance to hydrolysis catalyzed by many β-lactamases,has enhanced chemical stability, and is orally active. Oralabsorption is rapid and nearly complete. It has the highestoral bioavailability of the third-generation cephalosporins.Ceftibuten is excreted largely unchanged in the urine andhas a half-life of about 2.5 hours. Plasma protein binding ofthis cephalosporin is estimated to be 63%.
Ceftibuten possesses excellent potency against mostmembers of the Enterobacteriaceae family, H. influenzae,Neisseria spp., and M. catarrhalis. It is not active against S.aureus or P. aeruginosa and exhibits modest antistreptococcal activity. Ceftibuten is recommended in the managementof community-acquired respiratory tract, urinary tract, andgynecological infections.

Ceftibuten Preparation Products And Raw materials

Raw materials

Xylene 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Anisole Trifluoroacetic acid Methylmorpholine Aluminum chloride Tetrahydrofuran

Preparation Products

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View Lastest Price from Ceftibuten manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Ceftibuten 97519-39-6
Price: US $0.00/Kg/Bag
Min. Order: 1KG
Purity: 98%min
Supply Ability: 500kg
Release date: 2021-11-03

Shaanxi Dideu Medichem Co. Ltd

Product: Ceftibuten 97519-39-6
Price: US $0.00-0.00/Kg
Min. Order: 1KG
Purity: 99.0%+
Supply Ability: 300 MT
Release date: 2020-05-23

Shaanxi Dideu Medichem Co. Ltd

Product: Ceftibuten 97519-39-6
Price: US $0.00-0.00/Kg
Min. Order: 1KG
Purity: 99.0%+
Supply Ability: 300 MT
Release date: 2020-05-23

97519-39-6, CeftibutenRelated Search:

ceftibuten sidechain Ceftriaxone sodium Glycine Cefdinir Betaine Cefradine Cefixime Cephalexin ALTRENOGEST Cefpiramide acid CeftazidiMe ceftibuten dihydrate 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester Cefprozil hydrate 2-(2-AMINOTHIAZOL-4-YL)ETHYLAMINE 2-(2-AMINO-THIAZOL-4-YL)-ACETAMIDE 4-Thiazoleacetamide trans-Ceftibuten

(6r-(6-alpha,7-beta(z)))-yl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo

[6R-[(6α，7β(Z)]]-7-[[2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-5-thia-1-azabi-cyclo[4.2.0]oct-2-ene-2-carboxylic acid

Cedax：Isocef

(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate

(6R,7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-2-butenoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid

(6R,7R)-7α-[[(Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CS-1355

antibiotic7432s

cephalosporin7432-s

cephem

cis-ceftibutin

s7432

CEFTIBUTEN

7-[2-(2-amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4-carboxylic acid

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-, (6R,7R)-

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-, [6R-[6α,7β(Z)]]-

7432S

Ceftibuten (SCH 39720)

Ceftibutene

cis-Ceftibuten

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-, (6R,7R)-

Ceftibuten USP/EP/BP

97519-39-6

C15H14N4O6S2

MERIDIA

API