You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCeftibuten
Accession NumberDB01415
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-(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 acidNot AvailableNot Available
CeftibuteneNot AvailableNot Available
CeftibutenoNot AvailableNot Available
CeftibutenumNot AvailableNot Available
cis-CeftibutenNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftibutensuspension180 mg/5mLoralMacoven Pharmaceuticals2013-10-01Not AvailableUs
Ceftibutencapsule400 mgoralMacoven Pharmaceuticals2013-10-01Not AvailableUs
Cedaxcapsule400 mgoralSciele Pharma, Inc.1995-12-20Not AvailableUs
Cedaxsuspension18 mg/mLoralSciele Pharma, Inc.1995-12-20Not AvailableUs
Cedaxcapsule400 mgoralPernix Therapeutics, LLC1995-12-20Not AvailableUs
Cedaxsuspension90 mg/5mLoralPernix Therapeutics, LLC1995-12-20Not AvailableUs
Cedaxsuspension180 mg/5mLoralPernix Therapeutics, LLC2010-10-20Not AvailableUs
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number97519-39-6
WeightAverage: 410.425
Monoisotopic: 410.03547558
Chemical FormulaC15H14N4O6S2
InChI KeyUNJFKXSSGBWRBZ-BJCIPQKHSA-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
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
SMILES
[H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=C/CC(O)=O)\C1=CSC(N)=N1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Primary aromatic amine
  • N-acyl-amine
  • Dicarboxylic acid or derivatives
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
PharmacodynamicsCeftibuten is a third-generation cephalosporin antibiotic.
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.
AbsorptionRapidly absorbed following oral administration.
Volume of distribution
  • 0.21 L/kg [adult subjects]
  • 0.5 L/kg [fasting pediatric patients]
Protein bindingCeftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
Metabolism

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 eliminationCeftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
Half lifeNot Available
ClearanceNot Available
ToxicityOverdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5755
Blood Brain Barrier-0.9679
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5424
P-glycoprotein inhibitor INon-inhibitor0.9274
P-glycoprotein inhibitor IINon-inhibitor0.9586
Renal organic cation transporterNon-inhibitor0.929
CYP450 2C9 substrateNon-substrate0.8531
CYP450 2D6 substrateNon-substrate0.8293
CYP450 3A4 substrateNon-substrate0.6007
CYP450 1A2 substrateNon-inhibitor0.8787
CYP450 2C9 substrateNon-inhibitor0.8817
CYP450 2D6 substrateNon-inhibitor0.9191
CYP450 2C19 substrateNon-inhibitor0.8833
CYP450 3A4 substrateNon-inhibitor0.9625
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9387
Ames testNon AMES toxic0.7274
CarcinogenicityNon-carcinogens0.8961
BiodegradationNot ready biodegradable0.9688
Rat acute toxicity1.6446 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9848
hERG inhibition (predictor II)Non-inhibitor0.9305
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral400 mg
Suspensionoral18 mg/mL
Suspensionoral180 mg/5mL
Suspensionoral90 mg/5mL
Prices
Unit descriptionCostUnit
Cedax 400 mg capsule16.13USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States46346971992-10-012009-10-01
United States55995571994-02-042014-02-04
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0705 mg/mLALOGPS
logP0.31ALOGPS
logP-1.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)4.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area162.92 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.02 m3·mol-1ChemAxon
Polarizability38.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesJ01DD14
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Peptidoglycan synthase FtsI

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Peptidoglycan synthase FtsI P0AD68 Details

References:

  1. Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten—in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. Pubmed

2. Penicillin-binding protein 1A

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A P02918 Details

References:

  1. Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten—in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. Pubmed

3. Penicillin-binding protein 1B

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1B P02919 Details

References:

  1. Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten—in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. Pubmed

4. Penicillin-binding protein 2

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2 P0AD65 Details

References:

  1. Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten—in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. Pubmed

Transporters

1. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

References:

  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. Pubmed
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
  3. Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. Pubmed
  4. Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. Pubmed
  5. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  6. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. Pubmed
  7. Menon RM, Barr WH: Transporters involved in apical and basolateral uptake of ceftibuten into Caco-2 cells. Biopharm Drug Dispos. 2002 Nov;23(8):317-26. Pubmed

2. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

References:

  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. Pubmed
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  3. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

Comments
comments powered by Disqus
Drug created on July 23, 2007 07:06 / Updated on September 16, 2013 17:14