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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=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 Preparation Products And Raw materials

Raw materials

Preparation Products

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Ceftibuten Suppliers

BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
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65
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
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China Kouting Group Limited
Tel
+86 (21) 5811-6473 5811-6475
Fax
+86 (21) 6129-4103
Email
sales@koutingchina.com
Country
China
ProdList
496
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MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
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58
Shanghai TaoSu Biochemical Technology Co., Ltd.
Tel
021-33632979
Fax
021-34692979
Email
info@tsbiochem.com
Country
China
ProdList
8065
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Wuhan DKY Technology Co.,Ltd.
Tel
27-81302488 18007166089
Fax
027-81302088
Email
info@dkybpc.com
Country
China
ProdList
2024
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58
Hainan Manfangyuan Pharmaceutical Chemical Co., Ltd.
Tel
0898-66518050 13307521111
Fax
+86 (898) 6677-5768
Email
mfy001@hnmfy.com
Country
China
ProdList
85
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Wuhan Dahua Pharmaceutical Co., Ltd.
Tel
027-59262863 13277907145 3091977954
Fax
027-59420980
Country
China
ProdList
4943
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58
Hangzhou J&H Chemical Co., Ltd.
Tel
0571-+86-571-87396432
Fax
0571-87396431
Email
sales@jhechem.com
Country
China
ProdList
11487
Advantage
59
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66113011 18112977050
Email
cb6@aikonchem.com
Country
China
ProdList
16684
Advantage
50
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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:


  • (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