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Ceftibuten

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Name

Ceftibuten

EINECS 810-182-0
CAS No. 97519-39-6 Density 1.75 g/cm3
PSA 216.46000 LogP 0.86180
Solubility N/A Melting Point N/A
Formula C15H14N4O6S2 Boiling Point 966.4 °C at 760 mmHg
Molecular Weight 410.42 Flash Point 538.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 97519-39-6 (Ceftibuten) Hazard Symbols N/A
Synonyms

Ceftibuten [USAN:BAN:INN];Ceftibutin;Ceftibutene;Cephalosporin 7432-S;Ceftibutene [INN-French];Cedax (TN);Ceftibuten (USAN);Ceftibuteno [INN-Spanish];Cedax;Ceftibutenum [INN-Latin];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-(6alpha,7beta(Z)))-;Sch 39720;(+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;Cephem;

 

Ceftibuten Production

 Compounds (I) and formic acid diphenyl methyl ester dissolved in tetrahydrofuran, in the presence of sodium hydride, at 0 ~ 20°C, react 2h for getting the availability of high-yield compound (1I). (Ⅱ) and organic phosphorus reagents get Wittig reaction to be compound (Ⅲ). Then with trifluoroacetic acid in dichloromethane at 0 ~ 5 °C reaction 1.5h, hydrolysis, to get compound (Ⅳ). Then with cephalosporin (V), according to ordinary method,  obtained compound (Ⅵ) . Finally, in the presence of aluminum chloride with anisole,  heating to get.

Ceftibuten Specification

Ceftibuten is one kind of cephalosporin. It belongs to the Product Categories of API. The IUPAC Name of it is (6R,7R)-7-[[(E)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Its Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Reproductive Effect.

Physical properties about Ceftibuten are: (1)Molar mass:410.4249g/mol; (2)H bond acceptors: 10; (3)H bond donors: 5; (4)Freely Rotating Bonds: 6; (5)Polar Surface Area: 162.89 Å2; (6)Index of Refraction: 1.762; (7)Molar Refractivity: 96.19 cm3; (8)Molar Volume: 233.3 cm3; (9)Density: 1.75 g/cm3; (10)Flash Point: 538.3 °C; (11)Boiling Point: 966.4 °C at 760 mmHg; (12)Index of Refraction: 1.762; (13)Vapour Pressure: 0 mmHg at 25°C; (14)Surface Tension: 112.1 dyne/cm.

Uses of Ceftibuten: Ceftibuten is a third-generation cephalosporin antibiotic. Ceftibuten (CAS NO.97519-39-6) is used urinary tract infections, respiratory infections and gynecological infections caused by the susceptible ones. It is active against Haemophilus influenzae, Moraxella catarrhalis, Escherichia coli (K. pneumoniae, K. oxytoca), Proteus vulgaris, P. mirabils, P. providence, Salmonella sp., Shigella sp., Enterobacter sp. and Streptococcus sp.

Production of Ceftibuten: The compound (I) and carboxylic acid benzhydryl ester was dissolved in tetrahydrofuran, in the presence of sodium hydride, at 0 ~ 20 °C reaction 2h, the compound (1I) can be obtained in high yield. Then the compound (1I) will wittig react with the organic phosphorus reagent to generate a compound (III), its E / Z = 3/2. Then compound (III) with trifluoroacetic acid in dichloromethane, at 0 ~ 5 °C for 1.5h, obtained by hydrolyzing the compound (IV). Then and cephalosporins (V), according to a conventional method, i.e. in phosphorus oxychloride and N-methyl morpholine presence, in dichloromethane, at -20 °C reaction 20min, to obtain the compound (VI), theirE / Z = 85/15. Finally, in the presence of aluminum trichloride was heated in anisole, ceftibuten, and its E-isomer can be obtained, its E / Z = 85/15. But a mixture of the cis and trans isomers E type isomers into Z, slowly crystallized in the aqueous solution of the pH value of 3 - 4, the Z-form at the same time, E isomerization, thereby enablingceftibuten high yield.

Structure Descriptors of Ceftibuten:
(1)InChI: InChI=1S/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-/t10-,13-/m1/s1;
(2)InChIKey: InChIKey=UNJFKXSSGBWRBZ-BJCIPQKHSA-N;
(3)Smiles: N12[C@@H]([C@@H](C1=O)NC(=O)/C(=C\CC(=O)O)c1csc(n1)N)SCC=C2C(=O)O;

Toxicity of Ceftibuten as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Chemotherapy Vol. 37(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES
Chemotherapy Vol. 37(Suppl,

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