97519-39-6 Usage
Description
Ceftibuten is 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. It is a new, once-daily, orally active cephalosporin introduced as a treatment for Gram-negative bacteria-related urinary, respiratory tract, and gynecological infections. In vitro studies have shown that ceftibuten is superior to cefaclor and as active or slightly more active than cefixime and cefteram.
Uses
Used in Pharmaceutical Industry:
Ceftibuten is used as an antibiotic for the treatment of Gram-negative bacteria-related infections. It is particularly effective against urinary tract infections and respiratory tract infections.
Used in Urology:
Ceftibuten is used as a therapeutic agent for treating urinary tract infections caused by Gram-negative bacteria. Its once-daily dosing and oral administration make it a convenient treatment option for patients.
Used in Pulmonology:
Ceftibuten is used as a respiratory tract infection treatment, targeting infections caused by Gram-negative bacteria. Its effectiveness in combating these infections makes it a valuable tool in pulmonology.
Used in Gynecology:
Ceftibuten is used as a treatment for gynecological infections caused by Gram-negative bacteria. Its ability to target these infections makes it a useful antibiotic in the field of gynecology.
Used in Antidepressant Applications:
Ceftibuten is used as an antidepressant, potentially offering a new avenue for the treatment of depression.
Used in Anorexic Applications:
Ceftibuten is used as an anorexic agent, which may help in the management of appetite and weight control.
Used as a Serotonin and Dopamine Uptake Inhibitor:
Ceftibuten functions as an inhibitor of serotonin, norepinephrine, and dopamine uptake, which may contribute to its antidepressant and anorexic effects.
Brand Names:
Ceftibuten is marketed under the brand names Cedax (Schering) and Seftem.
Manufacturing Process
The 1st method of synthesisThe 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 synthesisFormulation 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
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.
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=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.
Check Digit Verification of cas no
The CAS Registry Mumber 97519-39-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,7,5,1 and 9 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 97519-39:
(7*9)+(6*7)+(5*5)+(4*1)+(3*9)+(2*3)+(1*9)=176
176 % 10 = 6
So 97519-39-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1+