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Showing drug card for Ceftibuten (DB01415)

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Version 2.5
Creation Date 2007-07-23 13:06:02
Update Date 2009-02-19 16:04:06
Primary Accession Number DB01415
Secondary Accession Number Not Available
Name Ceftibuten
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms Not Available
Brand Names
  1. Cedax
Brand Mixtures Not Available
Chemical IUPAC Name (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrate
Chemical Formula C15H18N4O8S2
Chemical Structure Structure
CAS Registry Number 97519-39-6
InChI Identifier InChI=1/C15H14N4O6S2.2H2O/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);2*1H2/b6-1-;;/t10-,13-;;/m1../s1/f/h18,20,24H,16H2;;
InChI Key SSWTVBYDDFPFAF-IBGKZCMODP
KEGG Drug D00922 Link Image
KEGG Compound C08117 Link Image
PubChem Compound 5282241 Link Image
PubChem Substance 10317 Link Image
ChEBI ID Not Available
PharmGKB ID PA448862 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic/ceftibuten.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ced1075.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Ceftibuten Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 446.4550
Monoisotopic Molecular Weight 446.0566
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES O.O.NC1=NC(=CS1)\C(=C\CC(O)=O)C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(O)=O
Canonical SMILES O.O.NC1=NC(=CS1)C(=CCC(O)=O)C(=O)NC1C2SCC=C(N2C1=O)C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Cephalosporins
ATC Codes
AHFS Codes Not Available
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.
Mechanism of Action Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Absorption Rapidly absorbed following oral administration.
Toxicity Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Protein Binding Ceftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
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.
Half Life Not Available
Dosage Forms
Form Route
Capsule Oral
Suspension Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
  3. PDRhealth Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Penicillin-binding proteins 1A/1B
  2. Oligopeptide transporter, small intestine isoform
Drug Target 1 [top]
Target 1 ID 633
Target 1 Name Penicillin-binding proteins 1A/1B
Target 1 Synonyms Not Available
Target 1 Gene Name pbpA
Target 1 Protein Sequence >Penicillin-binding proteins 1A/1B 
MTERKREHKDRKQNKNSPKNQSKVTKFLKWFFIGILLLGITAVTVVGIYVLSIIRSSPEL
DVQAIQSLNQPSILYDDQGNFMDNVITREQRYVVKSEEIPDNLKKAFVAIEDERFYEHKG
IDIKRIFGVIASNIKGKLSGSNTVQGASTITQQLIKNAVLTNEVSYERKIKEMYLALELE
KHLSKDEILTTYLNTIPMGGYQYGVSAAAQRFFSKNVSDLNLVECAYLGGLTQAPTSYDG
LSEANKENPSRYLNRTKSVLFKMHELGYISSEQYNDAINEIDTNGIKFTPNNKLSKTNFE
WFTRPAITQVKQDLMDKYKYTQEEVDKLIANGGLKIYTSMDRNLQNNVQKVLDDPNNYKA
ITNNPNEKNEDGVYKLQASATIIDYKTGHVKALVGGRGEQPAMSHNRAYYDLKSIGSATK
PLTVYGPAIDLGLGGAGSVVNDSPLSNKELSSTGYKDQPKNEYNSYRGPLTFREAIKISS
NLAAIKVANEVGVSNSIAYGEKLGLVYGPHSRGISTTALGQFQNDPNNPDGGNTYTLASA
FGVFGNNGVKTNAKLYTKVLDSHGNVILDTSTPEETKIFSPQASYIVYDMLKDQVESGSA
KSAKFGNIPVAGKTGTTTGDKDYLFAGLTPYYSAAIWIGYDKPREMRTSSGTVTSPIFGK
IMGLAHKDLQYKEVDNLVE
Target 1 Number of Residues 690
Target 1 Molecular Weight 75178
Target 1 Theoretical pI 9.09
Target 1 GO Classification
Function
binding
drug binding
penicillin binding
transferase activity
transferase activity, transferring glycosyl groups
transferase activity, transferring pentosyl groups
hydrolase activity
peptidase activity
catalytic activity
Process
cellular physiological process
cell organization and biogenesis
external encapsulating structure organization and biogenesis
cell wall organization and biogenesis
cell wall organization and biogenesis (sensu Bacteria)
cell wall biosynthesis (sensu Bacteria)
response to stimulus
response to abiotic stimulus
response to chemical stimulus
response to drug
response to antibiotic
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
cellular carbohydrate metabolism
peptidoglycan metabolism
peptidoglycan biosynthesis
Component
cell
external encapsulating structure
cell wall
cell wall (sensu Bacteria)
Target 1 General Function Cell wall/membrane/envelope biogenesis
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-52
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 18145626 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q8XJ01 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q8XJ01_CLOPE Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2040 bp 
ATGACTGAAAGAAAAAGAGAGCATAAAGATAGAAAGCAGAATAAAAATTCACCTAAAAAT
CAATCGAAAGTAACAAAATTTTTGAAATGGTTCTTTATAGGGATTCTGCTTCTAGGGATA
ACTGCCGTAACAGTAGTTGGAATTTACGTTCTTTCTATTATACGTTCATCTCCAGAGTTA
GATGTTCAGGCAATTCAATCTCTAAATCAGCCATCCATTCTTTACGATGATCAGGGAAAC
TTTATGGATAATGTTATAACTCGTGAACAACGTTATGTAGTTAAATCTGAAGAGATACCT
GATAACTTAAAAAAGGCTTTTGTAGCTATTGAAGACGAAAGATTTTATGAGCATAAAGGA
ATAGACATTAAAAGAATTTTTGGGGTAATAGCTTCTAATATTAAAGGTAAACTTTCAGGA
AGTAATACAGTTCAAGGGGCTTCAACCATAACTCAGCAACTTATAAAAAATGCCGTACTT
ACTAATGAAGTTAGTTATGAAAGAAAAATTAAAGAAATGTACTTAGCTTTGGAATTAGAA
AAGCACCTTTCAAAAGATGAAATCCTTACTACGTATTTAAATACAATTCCTATGGGTGGA
TACCAATATGGGGTTAGCGCAGCTGCTCAAAGATTTTTTAGTAAGAATGTTTCAGATTTG
AATTTAGTTGAGTGCGCTTATTTAGGAGGACTTACTCAAGCACCAACTTCTTATGATGGT
CTTTCAGAAGCAAATAAAGAAAATCCAAGTAGATATTTAAATAGAACTAAATCTGTACTA
TTTAAAATGCATGAACTTGGATATATTTCAAGTGAACAATATAATGACGCAATAAATGAA
ATTGACACAAATGGTATAAAATTCACACCAAATAATAAATTAAGTAAAACTAACTTTGAG
TGGTTCACAAGACCAGCTATAACTCAAGTTAAACAAGACTTAATGGATAAATATAAATAT
ACACAAGAGGAAGTTGACAAACTTATAGCTAATGGTGGATTAAAAATCTATACTTCAATG
GATAGAAATCTTCAAAATAATGTTCAAAAAGTTTTAGATGATCCAAATAACTATAAAGCT
ATAACTAATAATCCTAATGAAAAAAATGAAGATGGTGTTTATAAATTACAAGCATCTGCC
ACAATAATAGACTATAAAACAGGCCATGTTAAGGCTTTAGTTGGAGGAAGAGGGGAACAA
CCTGCTATGTCTCACAATAGAGCTTATTATGATTTAAAATCTATAGGTTCTGCAACAAAA
CCATTAACAGTTTATGGTCCTGCTATTGATTTAGGACTTGGTGGCGCTGGCTCTGTAGTA
AATGATTCTCCATTAAGTAATAAAGAGTTATCTTCTACAGGATATAAAGATCAACCTAAG
AATGAATACAATAGTTATAGAGGCCCTTTAACTTTTAGAGAAGCAATTAAAATCTCTAGT
AACTTAGCAGCCATAAAAGTTGCTAATGAAGTAGGTGTTTCAAACTCTATAGCTTATGGA
GAAAAATTAGGTCTTGTTTATGGACCTCATTCTAGAGGTATTTCCACAACAGCCTTAGGT
CAATTCCAAAATGACCCTAATAATCCTGATGGAGGAAATACTTATACTCTAGCTTCAGCC
TTCGGTGTTTTTGGTAATAACGGTGTTAAAACAAATGCTAAATTATATACAAAGGTATTA
GATTCTCATGGAAATGTAATTCTTGATACAAGTACTCCAGAAGAAACTAAAATATTTAGT
CCTCAAGCGTCTTATATAGTTTATGATATGCTTAAGGATCAAGTAGAAAGTGGCTCTGCA
AAATCTGCTAAATTTGGTAATATTCCTGTGGCGGGTAAAACAGGAACTACTACTGGAGAT
AAAGACTATTTATTTGCAGGATTAACTCCATATTATTCTGCGGCTATTTGGATTGGATAT
GATAAGCCTAGAGAAATGAGAACTAGTAGTGGTACTGTTACCTCTCCTATTTTCGGAAAA
ATAATGGGCTTAGCTCATAAAGACTTACAGTACAAAGAGGTTGACAACCTAGTGGAATAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Shimizu T, Ohtani K, Hirakawa H, Ohshima K, Yamashita A, Shiba T, Ogasawara N, Hattori M, Kuhara S, Hayashi H: Complete genome sequence of Clostridium perfringens, an anaerobic flesh-eater. Proc Natl Acad Sci U S A. 2002 Jan 22;99(2):996-1001. Epub 2002 Jan 15. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1539
Target 2 Name Oligopeptide transporter, small intestine isoform
Target 2 Synonyms
  1. Intestinal H(+)/peptide cotransporter
  2. Peptide transporter 1
  3. Solute carrier family 15 member 1
Target 2 Gene Name SLC15A1
Target 2 Protein Sequence >Oligopeptide transporter, small intestine isoform 
MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDNLSTAIYHTFV
ALCYLTPILGALIADSWLGKFKTIVSLSIVYTIGQAVTSVSSINDLTDHNHDGTPDSLPV
HVVLSLIGLALIALGTGGIKPCVSAFGGDQFEEGQEKQRNRFFSIFYLAINAGSLLSTII
TPMLRVQQCGIHSKQACYPLAFGVPAALMAVALIVFVLGSGMYKKFKPQGNIMGKVAKCI
GFAIKNRFRHRSKAFPKREHWLDWAKEKYDERLISQIKMVTRVMFLYIPLPMFWALFDQQ
GSRWTLQATTMSGKIGALEIQPDQMQTVNAILIVIMVPIFDAVLYPLIAKCGFNFTSLKK
MAVGMVLASMAFVVAAIVQVEIDKTLPVFPKGNEVQIKVLNIGNNTMNISLPGEMVTLGP
MSQTNAFMTFDVNKLTRINISSPGSPVTAVTDDFKQGQRHTLLVWAPNHYQVVKDGLNQK
PEKGENGIRFVNTFNELITITMSGKVYANISSYNASTYQFFPSGIKGFTISSTEIPPQCQ
PNFNTFYLEFGSAYTYIVQRKNDSCPEVKVFEDISANTVNMALQIPQYFLLTCGEVVFSV
TGLEFSYSQAPSNMKSVLQAGWLLTVAVGNIIVLIVAGAGQFSKQWAEYILFAALLLVVC
VIFAIMARFYTYINPAEIEAQFDEDEKKNRLEKSNPYFMSGANSQKQM
Target 2 Number of Residues 719
Target 2 Molecular Weight 78807
Target 2 Theoretical pI 8.64
Target 2 GO Classification
Function
transporter activity
peptide transporter activity
oligopeptide transporter activity
Process
physiological process
cellular physiological process
transport
peptide transport
oligopeptide transport
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 2 General Function Amino acid transport and metabolism
Target 2 Specific Function Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 1-21
  • 54-74
  • 83-103
  • 119-139
  • 162-182
  • 199-219
  • 277-297
  • 328-348
  • 362-382
  • 585-605
  • 620-640
  • 646-666
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 773588 Link Image
Target 2 UniProtKB/Swiss-Prot ID P46059 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name S15A1_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 Gene Sequence >2127 bp 
ATGGGAATGTCCAAATCACACAGTTTCTTTGGTTATCCCCTGAGCATCTTCTTCATCGTG
GTCAATGAGTTTTGCGAAAGATTTTCCTACTATGGAATGCGAGCAATCCTGATTCTGTAC
TTCACAAATTTCATCAGCTGGGATGATAACCTGTCCACCGCCATCTACCATACGTTTGTG
GCTCTGTGCTACCTGACGCCAATTCTCGGAGCTCTTATCGCCGACTCGTGGCTGGGAAAG
TTCAAGACCATTGTGTCGCTCTCCATTGTCTACACAATTGGACAAGCAGTCACCTCAGTA
AGCTCCATTAATGACCTCACAGACCACAACCATGATGGCACCCCCGACAGCCTTCCTGTG
CACGTGGTGCTGTCCTTGATCGGCCTGGCCCTGATAGCTCTCGGGACTGGAGGAATCAAA
CCCTGTGTGTCTGCGTTTGGTGGAGATCAGTTTGAAGAGGGCCAGGAGAAACAAAGAAAC
AGATTTTTTTCCATCTTTTACTTGGCTATTAATGCTGGAAGTTTGCTTTCCACAATCATC
ACACCCATGCTCAGAGTTCAACAATGTGGAATTCACAGTAAACAAGCTTGTTACCCACTG
GCCTTTGGGGTTCCTGCTGCTCTCATGGCTGTAGCCCTGATTGTGTTTGTCCTTGGCAGT
GGGATGTACAAGAAGTTCAAGCCACAGGGCAACATCATGGGTAAAGTGGCCAAGTGCATC
GGTTTTGCCATCAAAAATAGATTTAGGCATCGGAGTAAGGCATTTCCCAAGAGGGAGCAC
TGGCTGGACTGGGCTAAAGAGAAATACGATGAGCGGCTCATCTCCCAAATTAAGATGGTT
ACGAGGGTGATGTTCCTGTATATTCCACTCCCAATGTTCTGGGCCTTGTTTGACCAGCAG
GGCTCCAGGTGGACACTGCAGGCAACAACTATGTCCGGGAAAATCGGAGCTCTTGAAATT
CAGCCCGATCAGATGCAGACCGTGAACGCCATCCTGATCGTGATCATGGTCCCGATCTTC
GATGCTGTGCTGTACCCTCTCATTGCAAAATGTGGCTTCAATTTCACCTCCTTGAAGAAG
ATGGCAGTTGGCATGGTCCTGGCCTCCATGGCCTTTGTGGTGGCTGCCATCGTGCAGGTG
GAAATCGATAAAACTCTTCCAGTCTTCCCCAAAGGAAACGAAGTCCAAATTAAAGTTTTG
AATATAGGAAACAATACCATGAATATATCTCTTCCTGGAGAGATGGTGACACTTGGCCCA
ATGTCTCAAACAAATGCATTTATGACTTTTGATGTAAACAAACTGACAAGGATAAACATT
TCTTCTCCTGGATCACCAGTCACTGCTGTAACTGACGACTTCAAGCAGGGCCAACGCCAC
ACGCTTCTAGTGTGGGCCCCCAATCACTACCAGGTGGTAAAGGATGGTCTTAACCAGAAG
CCAGAAAAAGGGGAAAATGGAATCAGATTTGTAAATACTTTTAACGAGCTCATCACCATC
ACAATGAGTGGGAAAGTTTATGCAAACATCAGCAGCTACAATGCCAGCACATACCAGTTT
TTTCCTTCTGGCATAAAAGGCTTCACAATAAGCTCAACAGAGATTCCGCCACAATGTCAA
CCTAATTTCAATACTTTCTACCTTGAATTTGGTAGTGCTTATACCTATATAGTCCAAAGG
AAGAATGACAGCTGCCCTGAAGTGAAGGTGTTTGAAGATATTTCAGCCAACACAGTTAAC
ATGGCTCTGCAAATCCCGCAGTATTTTCTTCTCACCTGTGGCGAAGTGGTCTTCTCTGTC
ACGGGATTGGAATTCTCATATTCTCAGGCTCCTTCCAACATGAAGTCGGTGCTTCAGGCA
GGATGGCTGCTGACCGTGGCTGTTGGCAACATCATTGTGCTCATCGTGGCAGGGGCAGGC
CAGTTCAGCAAACAGTGGGCCGAGTACATTCTATTTGCCGCGTTGCTTCTGGTCGTCTGT
GTAATTTTTGCCATCATGGCTCGGTTCTATACTTACATCAACCCAGCGGAGATCGAAGCT
CAATTTGATGAGGATGAAAAGAAAAACAGACTGGAAAAGAGTAACCCATATTTCATGTCA
GGGGCCAATTCACAGAAACAGATGTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID SLC15A1 Link Image
Target 2 GenAtlas ID SLC15A1 Link Image
Target 2 HGNC ID HGNC:10920 Link Image
Target 2 Chromosome Location 13
Target 2 Locus 13q33-q34
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Liang R, Fei YJ, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH: Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization. J Biol Chem. 1995 Mar 24;270(12):6456-63. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  2. Pan X, Terada T, Okuda M, Inui K: Altered diurnal rhythm of intestinal peptide transporter by fasting and its effects on the pharmacokinetics of ceftibuten. J Pharmacol Exp Ther. 2003 Nov;307(2):626-32. Epub 2003 Sep 11. [PubMed Link Image]
  3. Menon RM, Barr WH: Comparison of ceftibuten transport across Caco-2 cells and rat jejunum mounted on modified Ussing chambers. Biopharm Drug Dispos. 2003 Oct;24(7):299-308. [PubMed Link Image]
  4. Shimizu Y, Masuda S, Nishihara K, Ji L, Okuda M, Inui K: Increased protein level of PEPT1 intestinal H+-peptide cotransporter upregulates absorption of glycylsarcosine and ceftibuten in 5/6 nephrectomized rats. Am J Physiol Gastrointest Liver Physiol. 2005 Apr;288(4):G664-70. Epub 2004 Nov 4. [PubMed Link Image]
  5. Terada T, Saito H, Mukai M, Inui KI: Identification of the histidine residues involved in substrate recognition by a rat H+/peptide cotransporter, PEPT1. FEBS Lett. 1996 Sep 30;394(2):196-200. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.