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Ceftibuten

Names

[ CAS No. ]:
97519-39-6

[ Name ]:
Ceftibuten

[Synonym ]:
7432 S
s7432
cis-Ceftibutin
ceftibutenum [INN_la]
Ceftibutene
antibiotic7432s
7432S
Seftem
Antibiotic 7432S
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)-
cephem
7b-[(Z)-2-(2-Aminothiazol-4-yl)-4-carboxy-2-butenoylamino]-3-cephem-4-carboxylic Acid
[6R-[6a,7b(Z)]]-7-[[2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic Acid
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-4-carboxy-2-butenoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftibuten
(6R,7R)-7-{[(2Z)-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
cephalosporin7432-s

Biological Activity

[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]

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial
Research Areas >> Infection
Natural Products >> Alkaloid

[References]

[1]. Wise R, et al. Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother, 1990. 26(2): p. 209-213.


[Related Small Molecules]

Puromycin 2HCl | Geneticin | Tunicamycin | Hygromycin B | Salinomycin | Avibactam sodium | Neomycin sulfate | Vaborbactam | Methicillin SodiuM | Rifampicin | Metronidazole | Carbenicillin disodium | Ceftazidime | Eravacycline dihydrochloride | cefotaxime sodium

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
966.4±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H14N4O6S2

[ Molecular Weight ]:
410.425

[ Flash Point ]:
538.3±34.3 °C

[ Exact Mass ]:
410.035461

[ PSA ]:
216.46000

[ LogP ]:
-0.96

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.762

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0367220
CHEMICAL NAME :
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-(6-alpha,7-beta(Z)))-
CAS REGISTRY NUMBER :
97519-39-6
LAST UPDATED :
199509
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C15-H14-N4-O6-S2
MOLECULAR WEIGHT :
410.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),804,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),804,1989 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
35 gm/kg/35D-I
TOXIC EFFECTS :
Gastrointestinal - other changes Kidney, Ureter, Bladder - urine volume decreased Biochemical - Metabolism (Intermediary) - other proteins
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),816,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
273 gm/kg/13W-I
TOXIC EFFECTS :
Gastrointestinal - other changes Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),858,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
54600 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume decreased Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in erythrocyte (RBC) count
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),919,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
72800 mg/kg/13W-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),883,1989 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12500 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 39,253,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
11 gm/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),990,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12500 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),1040,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
520 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 37(Suppl 1),1026,1989

Related Compounds

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