(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

• ChemBase ID: 1224
• Molecular Formular: C15H14N4O6S2
• Molecular Mass: 410.42486
• Monoisotopic Mass: 410.03547619
• SMILES: [C@@H]12N(C(=CCS1)C(=O)O)C(=O)[C@H]2NC(=O)/C(=C\CC(=O)O)/c1csc(n1)N
• Canonical SMILES: OC(=O)C/C=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O)/c1csc(n1)N
• 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
• InChIKey: UNJFKXSSGBWRBZ-BJCIPQKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: ceftibuteno
• Brand Name: Cedax
• Synonyms: Ceftibuten

Database IDs

• CAS Number: 97519-39-6
• PubChem SID: 160964684; 46507324
• PubChem CID: 5282242

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.9868503
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.8269622
• LogD (pH = 7.4): -6.7946153
• Log P: -1.4103966
• Molar Refractivity: 97.0238 cm^3
• Polarizability: 36.321697 Å^3
• Polar Surface Area: 162.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.31
• LOG S: -3.77
• Solubility (Water): 7.05e-02 g/l

DETAILS

DrugBank - DB01415

• Drug Groups: approved
• Description: Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally-administered agent. Cefalexin is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
• Indication: Used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
• Pharmacology: Ceftibuten is a third-generation cephalosporin antibiotic.
• Toxicity: Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: 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.
• Absorption: Rapidly absorbed following oral administration.
• Protein Binding: Ceftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
• Elimination: Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
• Distribution: * 0.21 L/kg [adult subjects]; * 0.5 L/kg [fasting pediatric patients]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com