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

General Information of Drug (ID: DR0801)
Drug Name
Haloperidol decanoate
Prodrug Info Haloperidol decanoate is the prodrug of Reduced haloperidol
Synonyms
Haloperidolum; Halopidol; Halopoidol; Halosten; Keselan; Lealgin compositum; Linton; McN-JR-1625; Mixidol; Pekuces; Peluces; Pernox; Serenace; Serenase; Serenelfi; Sernas; Sernel; Sigaperidol; Ulcolind; Uliolind; Vesalium; haloperidol; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one; 52-86-8; Aldo; Dozic; Halol; Aloperidin; Aloperidol; Aloperidolo; Aloperidolo [DCIT]; Aloperidolo [Italian]; Aloperidon; Bioperidolo; Brotopon; Einalon S; Eukystol; Fortunan; Galoperidol; Haldol; Haldol Solutab; Halidol; Halojust; Halopal; Depot haloperidol; HALOPERIDOL DECANOATE; Haldol decanoas; Haldol decanoate; Halomonth; Haloperidol depot; KD 136; KD-136; Neoperidole; R 13,672; R 13672; R-13672; 4-(4-Chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-4-piperidyl decanoate; 74050-97-8; AC20PJ4101; C31H41ClFNO3; Decanoic acid, 4-(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-4-piperidinyl ester; Decanoic acid, ester with 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone; EINECS 277-679-7; KD 16; UNII-AC20PJ4101
Indication Agitation/aggression [ICD11: 6D86] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 530.1 Topological Polar Surface Area 46.6
Heavy Atom Count 37 Rotatable Bond Count 16
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
52919
ChEBI ID
CHEBI:31664
CAS Number
74050-97-8
TTD Drug ID
D0D1AL
Formula
C31H41ClFNO3
Canonical SMILES
CCCCCCCCCC(=O)OC1(CCN(CC1)CCCC(=O)C2=CC=C(C=C2)F)C3=CC=C(C=C3)Cl
InChI
1S/C31H41ClFNO3/c1-2-3-4-5-6-7-8-11-30(36)37-31(26-14-16-27(32)17-15-26)20-23-34(24-21-31)22-9-10-29(35)25-12-18-28(33)19-13-25/h12-19H,2-11,20-24H2,1H3
InChIKey
GUTXTARXLVFHDK-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-chlorophenyl)-4-hydroxypiperidine DM004725
38282
Oxidation - N-dealkylation 1 [6]
Fluorobenzoylpropionic acid DM004727
2758337
Unclear 1 [7]
Haloperidol 1,2,3,6-tetrahydropyridine DM004724
171187
Other reaction - Dehydration 1 [6]
Haloperidol glucuronide DM004726
92131856
Conjugation - Glucuronidation 1 [6]
Haloperidol pyridinium ion derivative DM004723
9975463
Unclear 1 [7]
Reduced haloperidol DM004721
119265
Unclear 1 [6]
Haloperidol pyridinium ion derivative DM004723
9975463
Unclear 2 [6]
Haloperidol reduced pyridinium ion derivative DM004722
177961
Unclear 2 [6]
Haloperidol pyridinium ion derivative DM004723
9975463
Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005072 Haloperidol decanoate Reduced haloperidol Unclear CBR1 ... [6]
MR005075 Haloperidol decanoate Haloperidol 1,2,3,6-tetrahydropyridine Other reaction - Dehydration CYP3A4 [6]
MR005077 Haloperidol decanoate 4-(4-chlorophenyl)-4-hydroxypiperidine Oxidation - N-dealkylation CYP3A4 [6]
MR005078 Haloperidol decanoate Haloperidol glucuronide Conjugation - Glucuronidation UGT1A9 [6]
MR005079 Haloperidol decanoate Fluorobenzoylpropionic acid Unclear CYP1A2 [7]
MR005080 Haloperidol decanoate 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) Unclear CYP3A4 [7]
MR005076 Haloperidol 1,2,3,6-tetrahydropyridine Haloperidol pyridinium ion derivative Unclear Unclear [6]
MR005073 Reduced haloperidol Haloperidol reduced pyridinium ion derivative Unclear Unclear [6]
MR005074 Haloperidol reduced pyridinium ion derivative Haloperidol pyridinium ion derivative Unclear CYP3A4 [6]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_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
[4]
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
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[6]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 10  DME(s)
References
1 Haloperidol Decanoate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro characterization of the metabolism of haloperidol using recombinant cytochrome p450 enzymes and human liver microsomes. Drug Metab Dispos. 2001 Dec;29(12):1638-43.
3 Use of antidepressant drugs in schizophrenic patients with depression. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9.
4 Assessment of the contributions of CYP3A4 and CYP3A5 in the metabolism of the antipsychotic agent haloperidol to its potentially neurotoxic pyridinium metabolite and effect of antidepressants on the bioactivation pathway. Drug Metab Dispos. 2003 Mar;31(3):243-9.
5 Drug Interactions Flockhart Table
6 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
7 DrugBank(Pharmacology-Metabolism):Haloperidol decanoate

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