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

General Information of Drug (ID: DR0236)
Drug Name
Bromperidol
Synonyms
Bromoperidol; Bromperidolum [INN-Latin]; Impromen; Azurene; LYH6F7I22E; R 11333; RKLNONIVDFXQRX-UHFFFAOYSA-N; Tesoprel; bromperidol; 10457-90-6; 4-(4-(4-Bromophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone; 4-(4-(4-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone; 4-(4-(4-bromophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one; 4-(4-(p-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone; BRN 1552256; CAS-10457-90-6; CC 2489; EINECS 233-943-3; NCGC00016692-01; UNII-LYH6F7I22E
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 420.3 Topological Polar Surface Area 40.5
Heavy Atom Count 26 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2448
ChEBI ID
CHEBI:31305
CAS Number
10457-90-6
TTD Drug ID
D00SHQ
Formula
C21H23BrFNO2
Canonical SMILES
C1CN(CCC1(C2=CC=C(C=C2)Br)O)CCCC(=O)C3=CC=C(C=C3)F
InChI
1S/C21H23BrFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
InChIKey
RKLNONIVDFXQRX-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-fluorobenzoyl-propionic acid (FBPA) DM001654 N. A. Unclear 1 [3]
Bromperidol pyridinium DM001653 N. A. Unclear 1 [4]
Bromperidol to bromperidol 1,2,3,6-tetrahydropyridine DM001652 N. A. Other reaction - Dehydration 1 [4]
Reduced bromperidol DM001651 N. A. Oxidation - N-Dealkylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000463 Bromperidol Reduced bromperidol Oxidation - N-Dealkylation CYP3A4 [4]
MR000464 Bromperidol Bromperidol to bromperidol 1,2,3,6-tetrahydropyridine Other reaction - Dehydration CYP3A4 [4]
MR000465 Bromperidol Bromperidol pyridinium Unclear CYP3A4 [4]
MR000466 Bromperidol 4-fluorobenzoyl-propionic acid (FBPA) Unclear CYP1A1 ... [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]
References
1 ClinicalTrials.gov (NCT02307396) Evaluation of the Necessity of Long-term Pharmacological Treatment With Antipsychotics in Schizophrenic Patients.
2 CYP3A is responsible for N-dealkylation of haloperidol and bromperidol and oxidation of their reduced forms by human liver microsomes. Life Sci. 2000 Nov 3;67(24):2913-20.
3 Role of CYP3A in bromperidol metabolism in rat in vitro and in vivo Xenobiotica. 1999 Aug;29(8):839-46. doi: 10.1080/004982599238281.
4 Involvement of CYP3A4 in the metabolism of bromperidol in vitro. Pharmacol Toxicol. 2000 Mar;86(3):145-8.

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