Ceftibuten
Basic information
- CAS
97519-39-6- Standard SMILES
Nc1nc(/C(=C/CC(=O)O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=CCS[C@H]23)cs1- InChIKey
UNJFKXSSGBWRBZ-BJCIPQKHSA-N- Molecular formula
- C15H14N4O6S2
- Average molar mass
- 410.4 g/mol
- Monoisotopic mass
- 410.03547653
Overview
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. An orally-administered agent, ceftibuten is used as the dihydrate to treat urinary-tract and respiratory-tract infections. It has a role as an antibacterial drug. It is a cephalosporin and a dicarboxylic acid.
Names & identifiers
- Preferred name
- Ceftibuten
- IUPAC
- (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
- English name
- Ceftibuten
- Molecular formula
- C15H14N4O6S2
- Molecular weight
- 410.42
Names & synonyms
ceftibuten97519-39-6CeftibutenoCeftibuteneCeftibutenumSch 39720cis-ceftibutenSch-397207432-SDTXSID4045925CeftibutinACHN383
Show more names
cephems74327432SCS-1355Cedax：Isocefcis-ceftibutinantibiotic7432s
NSC-758925ACHN-383CHEBI:3510IW71N46B4Y(+)-(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 acidDTXCID2025925PF-06264006(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Database identifiers
- CAS
97519-39-6- PubChem CID
- 5282242
- DTXSID
DTXSID4045925- ChEMBL
CHEMBL1605- ChEBI
CHEBI:3510- UNII
- IW71N46B4Y
- EC Number
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 216 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 755
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Solubility7.05e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Physical DescriptionSolid
Collision Cross Section
191.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
188.81 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Boiling point
- 966 ℃ · 966℃
- Density
- 1.75 · 1.75±0.1 g/cm3(Predicted)
- RTECS
- 367220 · XI0367220
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P233, P260, P261, P271, P284, P304+P340, P317, P342+P316, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure RoutesRapidly absorbed following oral administration.
Toxicity SummaryCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Signs and SymptomsOverdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ceftibuten
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingCeftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
PharmacodynamicsCeftibuten is an antibiotic with bactericidal actions.
Mechanism of ActionCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Metabolism/Metabolites
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer. Route of Elimination: Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
FDA Pharmacological Classification
IW71N46B4Y
CEFTIBUTEN
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Ceftibuten is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Rapidly absorbed following oral administration.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…