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Ceftibuten

Ceftibuten structure

CAS No:
97519-39-6
Formula:
C15H14N4O6S2
Chemical Name:
Ceftibuten
Synonyms:
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)-;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)]]-;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)-;(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;S 7432;Antibiotic 7432S;7432S;Ceftibuten;Sch 39720;cis-Ceftibuten;Cephalosporin 7432-S;Ceftibuten (SCH 39720);Cedax
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic.IC50:Target: AntibacterialCeftibuten displayed high activity against Haemophilus influenzae and Branhamella catarrhalis. There was reduced activity against Streptococcus pneumoniae (MIC90 16 mg/l). The protein binding of Ceftibuten was 77% and the primary target site PBP 3. A high degree of stability to beta-lactamase hydrolysis was observed. [1]

Ceftibuten Basic Attributes

Molecular Weight：

410.42

Exact Mass：

410.42

EC Number：

1308068-626-2

Characteristics

PSA：

217

XLogP3：

-0.96

Appearance：

white to beige

Density：

1.8±0.1 g/cm3

Boiling Point：

966℃

Flash Point：

>110°(230°F)

Refractive Index：

1.762

Water Solubility：

soluble in aqueous solutions. Also soluble in DMSO

Storage Conditions：

2-8°C

Safety Information

wgk germany：

RTECS Number：

XI0367220

Precautionary statement(s)：

P261, P271, P285, P304+P312, P304+P340, P304+P341, P312, P342+P311, P501

Hazard Statements：

H332

Ceftibuten Use and Manufacturing

Methods of Manufacturing

Compound (I) and benzhydryl formate are dissolved in tetrahydrofuran and reacted in the presence of sodium hydride at 0-20°C for 2 hours to obtain compound (1I) in high yield. (II) Wittig reaction with organophosphorus reagent to produce compound (III), E/Z=3/2. Next, it is reacted with trifluoroacetic acid in dichloromethane at 0-5°C for 1.5h, and hydrolyzed to obtain compound (IV). Then, it is reacted with cephalosporin (V) according to the usual method, that is, in the presence of phosphorus oxychloride and N-methylmorpholine in dichloromethane at -20°C for 20 min to obtain compound (VI), which E/Z=85/15. Finally, in the presence of aluminum trichloride and heating in anisole, cefbutene and its E-form isomer can be obtained with E/Z=85/15. However, the cis-trans isomer mixture is in the aqueous solution with a Ph value of 3--4, because the E form will be isomerized to the Z form, while the Z form is slowly crystallized, the E form is continuously isomerized, and thus can be obtained High yield of cefebene.

Uses

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

Material

Tetrahydrofuran

Xylene

Trifluoroacetic acid

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Ceftibuten cas 97519-39-6

CAS No.: 97519-39-6

Grade: Analytical Reagent

Content: 99%

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