DT-Web

DB01415 - Ceftibuten


Identification
Name Ceftibuten
Accession Number DB01415
Type 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.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 410.425
Groups approved
Monoisotopic Weight 410.03547558
Pharmacology
Indication Used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
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.
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.
Route of elimination Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
Toxicity Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Peptidoglycan synthetase ftsI
Name Peptidoglycan synthetase ftsI
Gene Name ftsI
Pharmacological action yes
Actions inhibitor
References
  • 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
DTHybrid score 0.082
Penicillin-binding protein 1A
Name Penicillin-binding protein 1A
Gene Name mrcA
Pharmacological action yes
Actions inhibitor
References
  • 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
DTHybrid score 0.7107
Penicillin-binding protein 1B
Name Penicillin-binding protein 1B
Gene Name mrcB
Pharmacological action yes
Actions inhibitor
References
  • 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
DTHybrid score 0.694
Penicillin-binding protein 2
Name Penicillin-binding protein 2
Gene Name mrdA
Pharmacological action yes
Actions inhibitor
References
  • 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
DTHybrid score 0.0982

Transporters


Oligopeptide transporter, small intestine isoform
Name Oligopeptide transporter, small intestine isoform
Gene Name SLC15A1
Actions substrate,inhibitor
References
  • 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
  • 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
  • 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
  • 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
  • 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
  • Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. - Pubmed
  • 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
DTHybrid score 0.667
Oligopeptide transporter, kidney isoform
Name Oligopeptide transporter, kidney isoform
Gene Name SLC15A2
Actions inhibitor
References
  • 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
  • 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
  • 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
DTHybrid score 0.623

Predictions


Id Partner name Gene Name Score
5805 Penicillin-binding protein 1A ponA 0.7107
6185 Penicillin-binding protein 1A mrcA 0.7107
6799 Penicillin-binding protein 1A pbpA 0.7107
6186 Penicillin-binding protein 1B ponB 0.694
6822 Penicillin-binding protein 1b pbp1b 0.694
6844 Penicillin-binding protein 1b pbp1b 0.694
819 Penicillin-binding protein 4 dacB 0.253
6184 D-alanyl-D-alanine carboxypeptidase dacC dacC 0.2265
633 Penicillin-binding proteins 1A/1B pbpA 0.2
244 Angiotensin-converting enzyme ACE 0.1747
1729 Solute carrier family 22 member 6 SLC22A6 0.1656
118 Organic cation/carnitine transporter 2 SLC22A5 0.1486
867 Penicillin-binding protein 3 pbpC 0.1465
6119 Penicillin-binding protein 3 pbp3 0.1465
7154 Penicillin-binding protein 3 pbp3 0.1465
7157 Penicillin-binding protein 3 LMHCC_2184 0.1465
7162 Penicillin-binding protein 3 pbpB 0.1465
7172 Penicillin-binding protein 3 pbp3 0.1465
587 Serum albumin ALB 0.1399
3760 Penicillin-binding protein 5 precursor dacA 0.122
6067 Penicillin binding protein 2a mecA 0.1067
6142 Solute carrier family 22 member 8 SLC22A8 0.1052
115 Penicillin-binding protein 2 mrdA 0.0982
6118 Penicillin-binding protein 2 penA 0.0982
6187 Penicillin-binding protein 2 pbpA 0.0982
6686 Penicillin-binding protein 2 pbp2 0.0982
6939 Penicillin-binding protein 2 mrdA 0.0982
7163 Penicillin-binding protein 2 pbpA 0.0982
1 Peptidoglycan synthetase ftsI ftsI 0.082
6113 MecA PBP2' (penicillin binding protein 2') mecA 0.0809
332 Beta-lactamase blaZ 0.0749
2478 Beta-lactamase ampC 0.0749
2613 Beta-lactamase ampC 0.0749
2635 Beta-lactamase ampC 0.0749
2700 Beta-lactamase penP 0.0749
5445 Beta-lactamase blaB 0.0749
6019 Beta-lactamase SHV-7 0.0749
6701 Beta-lactamase cphA 0.0749
1024 Solute carrier family 22 member 11 SLC22A11 0.0656
1198 Serum paraoxonase/arylesterase 1 PON1 0.0592
6223 Penicillin-binding protein 1C pbpC 0.0592
471 Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+) SLC6A14 0.036
1385 Angiotensin-converting enzyme 2 ACE2 0.035
1405 Thiopurine S-methyltransferase TPMT 0.0346
6143 Solute carrier family 22 member 7 SLC22A7 0.034
2164 Multidrug resistance-associated protein 4 ABCC4 0.0295
1588 Multidrug resistance protein 1 ABCB1 0.028
234 Plasminogen PLG 0.0246
1757 Myeloperoxidase MPO 0.0242
4512 Cytochrome P450 3A4 CYP3A4 0.0239
56 Delta-aminolevulinic acid dehydratase ALAD 0.023
2356 Delta-aminolevulinic acid dehydratase hemB 0.023
3613 Delta-aminolevulinic acid dehydratase hemB 0.023
3674 Delta-aminolevulinic acid dehydratase hemB 0.023
3923 Cholinesterase BCHE 0.0203
230 ATP-binding cassette transporter sub-family C member 8 ABCC8 0.0203
2544 Bacterial leucyl aminopeptidase Not Available 0.0198
4604 Liver carboxylesterase 1 CES1 0.0175
6016 Cytochrome P450 2C19 CYP2C19 0.0172
3917 Methylenetetrahydrofolate reductase MTHFR 0.0164
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0155
3060 Leukotriene A-4 hydrolase LTA4H 0.0149
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.013
4119 Cytochrome P450 2D6 CYP2D6 0.0127
159 Penicillin-binding protein 2B penA 0.0123
6121 Penicillin-binding protein 2B penA 0.0123
4252 Penicillin-binding protein 5 dacA 0.0117
4757 Cytochrome P450 2C9 CYP2C9 0.0117
738 Monocarboxylate transporter 1 SLC16A1 0.0104
509 Thymidine kinase TK 0.0101
570 Thymidine kinase TK 0.0101
2559 Thymidine kinase TK 0.0101
3430 Thymidine kinase tdk 0.0101
3518 Thymidine kinase TK 0.0101
5301 Thymidine kinase tdk 0.0101
5771 Thymidine kinase ORF36 0.0101
7009 Thymidine kinase ORF36 0.0101
3810 Catechol O-methyltransferase COMT 0.0092
709 ATP-sensitive inward rectifier potassium channel 1 KCNJ1 0.0089
3426 Glutamine synthetase glnA 0.0089
3987 Glutamine synthetase GLUL 0.0089
338 DNA polymerase UL30 0.0087
379 DNA polymerase UL54 0.0087
697 DNA polymerase ORF28 0.0087
2482 DNA polymerase 43 0.0087
4104 DNA polymerase BALF5 0.0087
6140 Ileal sodium/bile acid cotransporter SLC10A2 0.0084
20 Prostaglandin G/H synthase 1 PTGS1 0.0078
318 Alpha-2A adrenergic receptor ADRA2A 0.0071
1141 Sialidase-1 NEU1 0.0068
64 Neuraminidase NA 0.0068
641 Neuraminidase NA 0.0068
2676 Neuraminidase NA 0.0068
3026 Neuraminidase NA 0.0068
3519 Neuraminidase NA 0.0068
6007 Neuraminidase NA 0.0068
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.006
6154 Multidrug and toxin extrusion protein 1 SLC47A1 0.0059
6153 Solute carrier organic anion transporter family member 4A1 SLCO4A1 0.0059
632 Alpha-1B adrenergic receptor ADRA1B 0.0056
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0054
5482 Sialidase-2 NEU2 0.0052
556 Alpha-1A adrenergic receptor ADRA1A 0.005
6106 Cytochrome P450 2C18 CYP2C18 0.0048
707 72 kDa type IV collagenase MMP2 0.0048
833 Organic cation/carnitine transporter 1 SLC22A4 0.0048
2461 D-alanyl-D-alanine carboxypeptidase Not Available 0.0046
5756 D-alanyl-D-alanine carboxypeptidase dac 0.0046
3961 G protein-activated inward rectifier potassium channel 4 KCNJ5 0.0046
4924 Cytochrome P450 2C8 CYP2C8 0.0043
65 Matrix metalloproteinase-9 Not Available 0.0039
521 ATP-binding cassette transporter sub-family C member 9 ABCC9 0.0038
132 ATP-binding cassette sub-family A member 1 ABCA1 0.0035
2184 Cystic fibrosis transmembrane conductance regulator CFTR 0.0034
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0033
4118 Cytochrome P450 3A5 CYP3A5 0.0033
866 Large neutral amino acids transporter small subunit 2 SLC7A8 0.0032
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0031
1181 Alpha-1-acid glycoprotein 1 ORM1 0.003
781 ATP-sensitive inward rectifier potassium channel 11 KCNJ11 0.003
245 Large neutral amino acids transporter small subunit 1 SLC7A5 0.0029
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0029
6107 Cytochrome P450 3A7 CYP3A7 0.0024
163 D(1B) dopamine receptor DRD5 0.0024
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0023
432 D(4) dopamine receptor DRD4 0.0023
638 D(3) dopamine receptor DRD3 0.0022
6151 Monocarboxylate transporter 10 SLC16A10 0.0022
776 Bile salt export pump ABCB11 0.0022
862 Multidrug resistance-associated protein 1 ABCC1 0.002
23 D(1A) dopamine receptor DRD1 0.002
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0019
831 D(2) dopamine receptor DRD2 0.0018
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0018
631 3-hydroxy-3-methylglutaryl-coenzyme A reductase HMGCR 0.0017
3387 3-hydroxy-3-methylglutaryl-coenzyme A reductase mvaA 0.0017
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0015
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0014
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0014
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0014
6024 Cytochrome P450 1A1 CYP1A1 0.0011
6030 Cytochrome P450 2B6 CYP2B6 0.0011
4200 Cytochrome P450 1A2 CYP1A2 0.0009
↑