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

General Information of Drug (ID: DR0958)
Drug Name
DUP-996
Synonyms
DuP-996; Dup 996; Linopirdine; Linopirdine [USAN:INN]; 1,3-Dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-2H-indol-2-one; 1-Phenyl-3,3-bis(4-pyridinylmethyl)-2-indolinone; 1-Phenyl-3,3-bis(pyridin-4-ylmethyl)indolin-2-one; 1-phenyl-3,3-bis(4-pyridylmethyl)indolin-2-one; 1-phenyl-3,3-bis(pyridin-4-ylmethyl)indol-2-one; 105431-72-9; 2H-Indol-2-one, 1,3-dihydro-1-phenyl-3,3-bis(4-pyridinylmethyl)-; C26H21N3O; CHEBI:34823; DSSTox_CID_25163; DSSTox_GSID_45163; DSSTox_RID_80713; I5TB3NZ94T; NCGC00015590-03; UNII-I5TB3NZ94T
Indication Cognitive impairment [ICD11: 6D71] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 391.5 Topological Polar Surface Area 46.1
Heavy Atom Count 30 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3932
PubChem SID
854025 ; 4659686 ; 7979778 ; 8152470 ; 11111362 ; 11114259 ; 12014138 ; 14927733 ; 17405293 ; 24263040 ; 24277846 ; 29223046 ; 46500471 ; 47206562 ; 48259468 ; 50070441 ; 50071084 ; 50104972 ; 50104973 ; 53777838 ; 57322057 ; 57654323 ; 77625157 ; 85177305 ; 85231103 ; 85788683 ; 90341523 ; 92304330 ; 103314113 ; 104304940 ; 121361490 ; 124749952 ; 124800387 ; 124880516 ; 124880517 ; 126407736 ; 126679061 ; 129783712 ; 135028219 ; 135650523 ; 137156939 ; 144203728 ; 162206962 ; 162224821 ; 163049819 ; 163564686 ; 170466342 ; 174006298 ; 178125900 ; 179149530
ChEBI ID
CHEBI:34823
CAS Number
105431-72-9
TTD Drug ID
D08YHS
Formula
C26H21N3O
Canonical SMILES
C1=CC=C(C=C1)N2C3=CC=CC=C3C(C2=O)(CC4=CC=NC=C4)CC5=CC=NC=C5
InChI
1S/C26H21N3O/c30-25-26(18-20-10-14-27-15-11-20,19-21-12-16-28-17-13-21)23-8-4-5-9-24(23)29(25)22-6-2-1-3-7-22/h1-17H,18-19H2
InChIKey
YEJCDKJIEMIWRQ-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
Linopirdine mono-N-oxide DM003170 N. A. Oxidation - N-oxidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003613 DUP-996 Linopirdine mono-N-oxide Oxidation - N-oxidation CYP [3]
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
References
1 The M-channel blocker linopirdine is an agonist of the capsaicin receptor TRPV1. J Pharmacol Sci. 2010;114(3):332-40.
2 Induction of cytochromes P-450 2B and 3A in mice following the dietary administration of the novel cognitive enhancer linopirdine. Drug Metab Dispos. 1994 Jan-Feb;22(1):65-73.
3 Determination of linopirdine and its N-oxide metabolites in rat plasma by liquid chromatography

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