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

General Information of Drug (ID: DR1291)
Drug Name
Pimozide
Synonyms
Pimozida [INN-Spanish]; Pimozidum; Pimozidum [INN-Latin]; Primozida [INN-Spanish]; R 6238; R-6238; pimozida; pimozide; 1-(1-(4,4-Bis(p-fluorophenyl)butyl)-4-piperidyl)-2-benzimidazolinone; 1-(4,4-Bis(p-fluorophenyl)butyl)-4-(2-oxo-1-benzimidazolinyl)piperidine; McN-JR 6238; McN-JR-6238; Opiran; 1-[1-[4,4-Bis(p-fluorophenyl)butyl]-4-piperidyl]-2-benzimidazolinone; 1HIZ4DL86F; 2062-78-4; BRN 0729089; C28H29F2N3O; CCRIS 9172; CHEMBL1423; EINECS 218-171-7; MLS000028410; MLS002702058; NSC 170984; Orap; UNII-1HIZ4DL86F
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 461.5 Topological Polar Surface Area 35.6
Heavy Atom Count 34 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
16362
PubChem SID
9769 ; 563187 ; 855710 ; 6706026 ; 7847626 ; 7980325 ; 8137196 ; 8149730 ; 8162258 ; 10321421 ; 11111615 ; 11112507 ; 11113804 ; 11335561 ; 11360800 ; 11363339 ; 11365901 ; 11368463 ; 11372540 ; 11373859 ; 11376625 ; 11447004 ; 11461772 ; 11466336 ; 11467456 ; 11484947 ; 11486231 ; 11488842 ; 11491266 ; 11492235 ; 11494259 ; 12013418 ; 14882544 ; 17405504 ; 24277923 ; 26612186 ; 26680826 ; 26747138 ; 26747139 ; 26751488 ; 26751978 ; 26751979 ; 29284219 ; 46507096 ; 47275121 ; 47275122 ; 47423792 ; 47572947 ; 47720184 ; 47720185
ChEBI ID
ChEBI:8212
CAS Number
2062-78-4
TTD Drug ID
D00KHM
Formula
C28H29F2N3O
Canonical SMILES
C1CN(CCC1N2C3=CC=CC=C3NC2=O)CCCC(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F
InChI
1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)
InChIKey
YVUQSNJEYSNKRX-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-Bis(4-Fluorophenyl)Butanoic Acid DM002847
88637
Unclear 1 [6]
5-hydroxypimozide DM002848 N. A. Oxidation - Hydroxylation 1 [7]
6-hydroxypimozide DM002849 N. A. Oxidation - Hydroxylation 1 [7]
DHBPI DM002846
88638
Oxidation - N-Dealkylation 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002038 Pimozide DHBPI Oxidation - N-Dealkylation CYP2D6 ... [7]
MR002039 Pimozide 4,4-bis(4-fluorophenyl) butyric acid Unclear CYP3A4 [6]
MR002040 Pimozide 5-hydroxypimozide Oxidation - Hydroxylation CYP2D6 [7]
MR002041 Pimozide 6-hydroxypimozide Oxidation - Hydroxylation CYP2D6 [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
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
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
⏷ Show the Full List of 9  DME(s)
References
1 Pimozide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification and characterization of human cytochrome P450 isoforms interacting with pimozide. J Pharmacol Exp Ther. 1998 May;285(2):428-37.
3 The influence of the CYP3A4*22 polymorphism and CYP2D6 polymorphisms on serum concentrations of aripiprazole, haloperidol, pimozide, and risperidone in psychiatric patients. J Clin Psychopharmacol. 2015 Jun;35(3):228-36.
4 Drug Interactions Flockhart Table
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 LABEL:IMOZIDE tablet
7 The Respective Roles of CYP3A4 and CYP2D6 in the Metabolism of Pimozide to Established and Novel Metabolites Drug Metab Dispos. 2020 Nov;48(11):1113-1120. doi: 10.1124/dmd.120.000188.

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