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

General Information of Drug (ID: DR1646)
Drug Name
Trimebutine
Synonyms
Trimebutine maleate; Trimebutine maleate salt; LORDFXWUHHSAQU-UHFFFAOYSA-N; TRIMEBUTINE FREE BASE; Trimebutine [INN:BAN:DCF]; Trimebutino; Trimebutino [INN-Spanish]; Trimebutinum [INN-Latin]; Trimedat; W-111163; trimebutine; 2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate; 2-Dimethylamino-2-phenylbutyl 3,4,5-trimethoxybenzoat; 3,4,5-Trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester; 39133-31-8; Benzoic acid, 3,4,5-trimethoxy-, 2-(dimethylamino)-2-phenylbutyl ester; C22H29NO5; EINECS 254-309-2
Indication Irritable bowel syndrome [ICD11: DD91] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 387.5 Topological Polar Surface Area 57.2
Heavy Atom Count 28 Rotatable Bond Count 10
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5573
ChEBI ID
CHEBI:94458
CAS Number
39133-31-8
TTD Drug ID
D0E0CT
Formula
C22H29NO5
Canonical SMILES
CCC(COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C
InChI
1S/C22H29NO5/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5/h8-14H,7,15H2,1-6H3
InChIKey
LORDFXWUHHSAQU-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
2-dimethylamino-2-phenylbutan-1-ol DM005806
3016037
Hydrolysis - Hydrolysis 1 [4] , [5]
Nortrimebutine DM005802
134748
Oxidation - N-demethylation 1 [4] , [5] , [6]
2-methylamino-2-phenylbutan-1-ol DM005804
10726043
Oxidation - N-demethylation 2 [4] , [5]
2-methylamino-2-phenylbutan-1-ol DM005804
10726043
Hydrolysis - Hydrolysis 2 [4] , [5] , [6]
N-didesmethyltrimebutine DM005803
6426878
Oxidation - N-demethylation 2 [4] , [5] , [6]
2-amino-2-phenylbutan-1-ol DM005805
11194531
Oxidation - N-demethylation 3 [4] , [5]
2-amino-2-phenylbutan-1-ol DM005805
11194531
Oxidation - N-demethylation 3 [4] , [5] , [6]
2-amino-2-phenylbutan-1-ol DM005805
11194531
Hydrolysis - Hydrolysis 3 [4] , [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006199 Trimebutine Nortrimebutine Oxidation - N-demethylation Unclear [4], [5], [6]
MR006204 Trimebutine 2-dimethylamino-2-phenylbutan-1-ol Hydrolysis - Hydrolysis Unclear [4], [5]
MR006205 2-dimethylamino-2-phenylbutan-1-ol 2-methylamino-2-phenylbutan-1-ol Oxidation - N-demethylation Unclear [4], [5]
MR006200 Nortrimebutine N-didesmethyltrimebutine Oxidation - N-demethylation Unclear [4], [5], [6]
MR006201 Nortrimebutine 2-methylamino-2-phenylbutan-1-ol Hydrolysis - Hydrolysis Unclear [4], [5], [6]
MR006203 2-methylamino-2-phenylbutan-1-ol 2-amino-2-phenylbutan-1-ol Oxidation - N-demethylation Unclear [4], [5], [6]
MR006202 N-didesmethyltrimebutine 2-amino-2-phenylbutan-1-ol Hydrolysis - Hydrolysis Unclear [4], [5], [6]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [3]
⏷ Show the Full List of 25  DME(s)
References
1 ClinicalTrials.gov (NCT01507922) Comparative Efficacy and Safety of Fenoverine.
2 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Studies of metabolic pathways of trimebutine by simultaneous administration of trimebutine and its deuterium-labeled metabolite
5 [Metabolism of trimebutine maleate, a gastrointestinal tract motility regulator in rats and mice: characterization and quantification of metabolites in urine, bile and plasma]
6 Quantitative determination of trimebutine maleate and its three metabolites in human plasma by liquid chromatography-tandem mass spectrometry

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