Ceftibuten

Ceftibuten Basic information
Product Name:Ceftibuten
Synonyms:(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
CAS:97519-39-6
MF:C15H14N4O6S2
MW:410.42
EINECS:810-182-0
Product Categories:MERIDIA;API
Mol File:97519-39-6.mol
Ceftibuten Structure
Ceftibuten Chemical Properties
Boiling point 966℃
density 1.75±0.1 g/cm3(Predicted)
RTECS XI0367220
Fp >110°(230°F)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility Soluble in aqueous solutions. Also soluble in DMSO
pka2.99±0.50(Predicted)
form powder
color white to beige
Safety Information
WGK Germany 3
MSDS Information
Ceftibuten Usage And Synthesis
DescriptionCeftibuten 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.
OriginatorShionogi (Japan)
Usesanorexic, antidepressant, inhibitor of 5HT, norepinephrine & dopamine uptake
DefinitionChEBI: 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 ProcessThe 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 nameCedax (Schering);Seftem.
Therapeutic FunctionAntibiotic
Antimicrobial activityA 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 DescriptionChemical structure: ?-lactam
Biochem/physiol ActionsCeftibuten is a third generation cephalosporin antibiotic
PharmacokineticsCeftibuten 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 UseCeftibuten (Cedax) is a recently introduced, chemicallynovel analog of the oximino cephalosporins in which anolefinic methylene group (C=CHCH2-) 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 sidechain ceftibuten dihydrate Betaine Cephalexin 7-amino-3-Nor cephalosporanic acid Inter.for ceftibuten,ceftizoxime(7-ANCA) Cefradine Ceftriaxone sodium Cefixime ALTRENOGEST 2-(2-AMINOTHIAZOL-4-YL)ETHYLAMINE 2-(2-AMINO-THIAZOL-4-YL)-ACETAMIDE Cefpiramide acid Glycine 4-Thiazoleacetamide CeftazidiMe Ceftibuten Cefdinir AMINO ACIDS

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