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

General Information of Drug (ID: DR0894)
Drug Name
HSR-803
Synonyms
Ganaton; ITOPRIDE HCl; Itopride (hydrochloride); Q-201260; itopride hydrochloride; 122892-31-3; 2H9NV66W0I; C20H27ClN2O4; DSSTox_CID_26693; DSSTox_GSID_46693; DSSTox_RID_81827; HSR-803; HSR803; Hsr 803; Itax; MFCD00881710; N-((4-(2-(Dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxybenzamide monohydrochloride; N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4-dimethoxidebenzamide hydrochloride; N-(4-(2-(dimethylamino)ethoxy)benzyl)-3,4-dimethoxybenzmide; UNII-2H9NV66W0I; n-[4-(2-dimethylaminoethoxy)benzyl]-3,4-dimethoxybenzamide hcl
Indication Functional nausea/vomiting [ICD11: DD90] Phase 3 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 394.9 Topological Polar Surface Area 60
Heavy Atom Count 27 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
129791
CAS Number
122892-31-3
Formula
C20H27ClN2O4
Canonical SMILES
CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C=C2)OC)OC.Cl
InChI
1S/C20H26N2O4.ClH/c1-22(2)11-12-26-17-8-5-15(6-9-17)14-21-20(23)16-7-10-18(24-3)19(13-16)25-4;/h5-10,13H,11-12,14H2,1-4H3,(H,21,23);1H
InChIKey
ZTOUXLLIPWWHSR-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
Itopride N-oxide DM003222
71433796
Oxidation - N-oxidation 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003658 HSR-803 Itopride N-oxide Oxidation - N-oxidation FMO3 [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[2]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[3] , [4]
References
1 ClinicalTrials.gov (NCT00112177) Effect of Itopride, on Symptoms of Functional Dyspepsia, Such as Indigestion, Bloating, Inability to Finish a Meal.
2 Development of a physiologically based pharmacokinetic model to predict the effects of flavin-containing monooxygenase 3 (FMO3) polymorphisms on itopride exposure. Biopharm Drug Dispos. 2017 Sep;38(6):389-393.
3 The involvement of flavin-containing monooxygenase but not CYP3A4 in metabolism of itopride hydrochloride, a gastroprokinetic agent: comparison with cisapride and mosapride citrate. Drug Metab Dispos. 2000 Oct;28(10):1231-7.
4 Effect of two-linked mutations of the FMO3 gene on itopride metabolism in Chinese healthy volunteers. Eur J Clin Pharmacol. 2014 Nov;70(11):1333-8.

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