Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0557)
Drug Name
Ebastine
Prodrug Info Ebastine is the prodrug of Carebastine
Synonyms
Ebastel; Ebastin; Ebastina [Spanish]; Ebastinum [Latin]; Estivan; Evastel; Kestin; Kestine; LAS W-090; RP 64305; Bactil; RP-64305; TQD7Q784P1; ebastine; 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one; 1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone; 4'-tert-Butyl-4-(4-(diphenylmethoxy)piperidino)butyrophenone; 4-Diphenylmethoxy-1-(3-(4-tert-butylbenzoyl)propyl)piperidine; 90729-43-4; C32H39NO2; CHEMBL305660; MFCD00865661; NCGC00164603-01; UNII-TQD7Q784P1
Indication Irritable bowel syndrome [ICD11: DD91] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 469.7 Topological Polar Surface Area 29.5
Heavy Atom Count 35 Rotatable Bond Count 10
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3191
ChEBI ID
CHEBI:31528
CAS Number
90729-43-4
Formula
C32H39NO2
Canonical SMILES
CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)OC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
InChIKey
MJJALKDDGIKVBE-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-(4-tert-butylphenyl)-4-oxobutanal DM016166
54343088
Oxidation - N-dealkylation 1 [5]
Desalkylebastine DM003268
3017584
Oxidation - N-dealkylation 1 [5]
Ebastine Metabolite M-5c DM017715 N. A. Unclear - Unclear 1 [6]
Hydroxyebastine DM006604
11992145
Oxidation - Hydroxylation 1 [3]
Carebastine DM006605
65820
Unclear - Unclear 2 [7] , [3]
Ebastine Metabolite M-4 DM017713 N. A. Unclear - Unclear 2 [6]
Ebastine Metabolite M-4 DM017713 N. A. Conjugation - Mono-methylation 2 [6]
Ebastine Metabolite M-5a DM017716 N. A. Unclear - Unclear 2 [6]
Desalkylebastine DM003268
3017584
Oxidation - N-dealkylation 3 [3]
Ebastine Metabolite M-3 DM017712 N. A. Unclear - Unclear 3 [6]
Ebastine Metabolite M-3 DM017712 N. A. Unclear - Unclear 3 [5] , [6]
Ebastine Metabolite M-5b DM017714 N. A. Unclear - Unclear 3 [6]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009218 Ebastine Hydroxy-ebastine Oxidation - Hydroxylation CYP2J2 ... [3]
MR009225 Ebastine Ebastine Metabolite M-5c Unclear - Unclear Unclear [6]
MR009228 Ebastine 4-(4-tert-butylphenyl)-4-oxobutanal Oxidation - N-dealkylation CYP3A4 [5]
MR009229 Ebastine Deslakylebastine Oxidation - N-dealkylation CYP3A4 [5]
MR009226 Ebastine Metabolite M-5c Ebastine Metabolite M-4 Unclear - Unclear Unclear [6]
MR009219 Hydroxy-ebastine Carebastine Unclear - Unclear CYP [7], [3]
MR009222 Hydroxy-ebastine Ebastine Metabolite M-4 Conjugation - Mono-methylation Unclear [6]
MR009227 Hydroxy-ebastine Ebastine Metabolite M-5a Unclear - Unclear Unclear [6]
MR009220 Carebastine Ebastine Metabolite M-3 Unclear - Unclear CYP4F2 [5], [6]
MR009221 Carebastine Deslakylebastine Oxidation - N-dealkylation CYP3A4 [3]
MR009223 Ebastine Metabolite M-4 Ebastine Metabolite M-5b Unclear - Unclear Unclear [6]
MR009224 Ebastine Metabolite M-4 Ebastine Metabolite M-3 Unclear - Unclear Unclear [6]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[]
Cytochrome P450 4F12 (CYP4F12) DME0135 Homo sapiens
CP4FC_HUMAN
1.14.14.1
[4]
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[4]
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[5]
⏷ Show the Full List of 7  DME(s)
References
1 ClinicalTrials.gov (NCT01908465) Peripheral Histamine 1 Receptor Blockade in IBS: Multicenter Trial.
2 Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity. Drug Metab Dispos. 2012 May;40(5):943-51.
3 Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A. Drug Metab Dispos. 2006 Nov;34(11):1793-7.
4 cDNA cloning and expression of a novel cytochrome p450 (cyp4f12) from human small intestine. Biochem Biophys Res Commun. 2001 Feb 2;280(4):1135-41.
5 Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes
6 Identification of rat faecal metabolites of ebastine by B/E linked scanning liquid secondary ion mass spectrometry
7 Comparative pharmacokinetics of the histamine H1-receptor antagonist ebastine and its active metabolite carebastine in rats, guinea pigs, dogs and monkeys

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