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

General Information of Drug (ID: DR0856)
Drug Name
Iloperidone
Synonyms
Iloperidone; Iloperidone (Fanapt); Iloperidone(Fanapt); VPO7KJ050N; Zomaril; 1-(4-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propoxy)-3-methoxyphenyl)ethanone; 1-[4-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone; Fanapt; Fanapta; HP 873; HP-873; 133454-47-4; 4'-(3-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidino)propoxy)-3'-methoxyacetophenone; C24H27FN2O4; CHEBI:65173; CHEMBL14376; DSSTox_CID_28986; DSSTox_GSID_49060; DSSTox_RID_83251; NCGC00188864-01; UNII-VPO7KJ050N
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 426.5 Topological Polar Surface Area 64.8
Heavy Atom Count 31 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
71360
PubChem SID
8194581 ; 12014542 ; 14905142 ; 17396835 ; 43127698 ; 47359860 ; 47359861 ; 47731199 ; 48404440 ; 50064358 ; 51401239 ; 57318156 ; 85209859 ; 92712438 ; 93301492 ; 99246148 ; 99437181 ; 103176655 ; 103856472 ; 103942259 ; 104350273 ; 109693466 ; 117566372 ; 118050578 ; 124757285 ; 124899318 ; 125164089 ; 125340171 ; 126625565 ; 126656709 ; 126666080 ; 129711844 ; 131297754 ; 134339308 ; 135029478 ; 135587716 ; 135650377 ; 135692163 ; 135697544 ; 136367918 ; 137249342 ; 142584651 ; 144116064 ; 144207159 ; 152344064 ; 160645064 ; 162011651 ; 162037626 ; 162172136 ; 163123672
ChEBI ID
CHEBI:65173
CAS Number
133454-47-4
TTD Drug ID
D0M8VE
Formula
C24H27FN2O4
Canonical SMILES
CC(=O)C1=CC(=C(C=C1)OCCCN2CCC(CC2)C3=NOC4=C3C=CC(=C4)F)OC
InChI
1S/C24H27FN2O4/c1-16(28)18-4-7-21(23(14-18)29-2)30-13-3-10-27-11-8-17(9-12-27)24-20-6-5-19(25)15-22(20)31-26-24/h4-7,14-15,17H,3,8-13H2,1-2H3
InChIKey
XMXHEBAFVSFQEX-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
Iloperidone P88 DM004304
9823904
Reduction - Carbonyl reduction 1 [4]
Iloperidone P89 DM004306
11742411
Oxidation - O-demethylation 1 [4]
Iloperidone P95 DM004305
23786476
Oxidation - Hydrolyzationn 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004664 Iloperidone Iloperidone P88 Reduction - Carbonyl reduction Unclear [4]
MR004665 Iloperidone Iloperidone P95 Oxidation - Hydrolyzationn CYP2D6 [4]
MR004666 Iloperidone Iloperidone P89 Oxidation - O-demethylation CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
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
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Iloperidone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Influences of CYP2D6*10 polymorphisms on the pharmacokinetics of iloperidone and its metabolites in Chinese patients with schizophrenia: a population pharmacokinetic analysis. Acta Pharmacol Sin. 2016 Nov;37(11):1499-1508.
3 Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93.
4 Iloperidone: chemistry, pharmacodynamics, pharmacokinetics and metabolism, clinical efficacy, safety and tolerability, regulatory affairs, and an opinion. Expert Opin Drug Metab Toxicol. 2010 Dec;6(12):1551-64.

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