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

General Information of Drug (ID: DR1905)
Drug Name
LAS-17177
Synonyms
Blaston; Cidine; Cinitaprida; Cinitaprida [INN-Spanish]; Cinitapride; Cinitapride (INN); Cinitapride [INN]; Cinitapride hydrogen tartrate; Cinitapridum; Cinitapridum [INN-Latin]; Cinmove; Cintapro; Paxapride; Paxapride (TN); R8I97I2L24; SCHEMBL476454; cinitapride tartrate; (non-labelled)Cinitapride-d5; 4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide; 66564-14-5; AC1L2AM4; AC1Q1YMD; AKOS015909742; BCP04096; C21H30N4O4; CHEBI:135642; CHEMBL2104523; DB08810; SCHEMBL19235643; UNII-R8I97I2L24; cidin
Indication Functional nausea/vomiting [ICD11: DD90] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 402.5 Topological Polar Surface Area 113
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
68867
PubChem SID
8192404 ; 15079777 ; 43125380 ; 50306778 ; 51091999 ; 57317118 ; 87692390 ; 103823385 ; 104343273 ; 117379540 ; 135026488 ; 135029027 ; 135367578 ; 136006041 ; 136946491 ; 137138357 ; 137213478 ; 144115833 ; 152049161 ; 160708580 ; 160969717 ; 162178723 ; 164838455 ; 175427098 ; 179150888 ; 226793538 ; 241117457
ChEBI ID
CHEBI:135642
CAS Number
66564-14-5
TTD Drug ID
D0L3EO
Formula
C21H30N4O4
Canonical SMILES
CCOC1=CC(=C(C=C1C(=O)NC2CCN(CC2)CC3CCC=CC3)[N+](=O)[O-])N
InChI
1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)
InChIKey
ZDLBNXXKDMLZMF-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-amino-2-ethoxy-5-nitrobenzamido)-1-(cyclohex-3-enylmethyl)piperidine 1-oxide, DM003263
129850164
Oxidation - Hydrolyzationn 1 [3]
4-amino-2-ethoxy-5-nitro-N-(piperidin-4-yl)benzamide DM003262
124519545
Oxidation - Hydrolyzationn 1 [3]
4-amino-2-ethoxy-N-[1-((3-hydroxycyclohexen-3-yl)methyl)piperidin-4-yl]- 5-nitrobenzamide DM003264
129850161
Oxidation - Hydrolyzationn 1 [3]
4-amino-2-ethoxy-N-[1-((4-hydroxycyclohexen_x0002_3-yl)methyl)piperidin-4-yl]- 5-nitrobenzamide DM003265 N. A. Oxidation - Hydrolyzationn 1 [3]
4-amino-N-[1-((3,4-dihydroxycyclohexyl)methyl)-piperidin-4-yl]-2-ethoxy-5-nitrobenzamide; DM003261
129850136
Oxidation - Hydrolyzationn 1 [3]
LAS-17177 Metabolite M10 DM003266 N. A. Oxidation - Hydrolyzationn 1 [3]
LAS-17177 Metabolite M13 DM003267 N. A. Oxidation - Hydrolyzationn 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003696 LAS-17177 4-amino-N-[1-((3,4-dihydroxycyclohexyl)methyl) piperidin-4-yl]-2-ethoxy-5-nitrobenzamide; Oxidation - Hydrolyzationn Unclear [3]
MR003697 LAS-17177 4-amino-2-ethoxy-5-nitro-N-(piperidin-4-yl)benzamide Oxidation - Hydrolyzationn Unclear [3]
MR003698 LAS-17177 4-(4-amino-2-ethoxy-5-nitrobenzamido)-1-(cyclohex-3-enylmethyl)piperidine 1-oxide, Oxidation - Hydrolyzationn Unclear [3]
MR003699 LAS-17177 4-amino-2-ethoxy-N-[1-((3-hydroxycyclohexen-3-yl)methyl)piperidin-4-yl]- 5-nitrobenzamide Oxidation - Hydrolyzationn Unclear [3]
MR003700 LAS-17177 4-amino-2-ethoxy-N-[1-((4-hydroxycyclohexen_x0002_3-yl)methyl)piperidin-4-yl]- 5-nitrobenzamide Oxidation - Hydrolyzationn Unclear [3]
MR003701 LAS-17177 LAS-17177 Metabolite M10 Oxidation - Hydrolyzationn Unclear [3]
MR003702 LAS-17177 LAS-17177 Metabolite M13 Oxidation - Hydrolyzationn Unclear [3]
⏷ 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 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT01355276) Efficacy and Safety of Cinitapride Tablets in the Treatment of Mild to Moderate Functional Dyspepsia.
2 The prokinetic cinitapride has no clinically relevant pharmacokinetic interaction and effect on QT during coadministration with ketoconazole. Drug Metab Dispos. 2007 Jul;35(7):1149-56.
3 Characterization of in vitro metabolic profiles of cinitapride obtained with liver microsomes of humans and various mammal species using UHPLC and chemometric methods for data analysis

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