Details of the Drug

General Information of Drug (ID: DM24XYQ)

Drug Name
Bromperidol
Synonyms
bromperidol; 10457-90-6; Impromen; Bromoperidol; Tesoprel; Azurene; 4-(4-(4-bromophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one; UNII-LYH6F7I22E; Bromperidolum [INN-Latin]; R 11333; EINECS 233-943-3; 4-(4-(4-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone; CC 2489; BRN 1552256; LYH6F7I22E; 4-(4-(p-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone; RKLNONIVDFXQRX-UHFFFAOYSA-N; 4-(4-(4-Bromophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone; NCGC00016692-01; CAS-10457-90-6
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Approved [1]
ATC Code
N05AD06: Bromperidol
N05AD: Butyrophenone derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AD06: Bromperidol
N05AD: Butyrophenone derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AD06: Bromperidol
N05AD: Butyrophenone derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 420.3
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Elimination
0.5% of drug is excreted from urine in the unchanged form [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.9818 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.09 mg/mL [2]
Chemical Identifiers
Formula
C21H23BrFNO2
IUPAC Name
4-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
Canonical SMILES
C1CN(CCC1(C2=CC=C(C=C2)Br)O)CCCC(=O)C3=CC=C(C=C3)F
InChI
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
Cross-matching ID
PubChem CID
2448
ChEBI ID
CHEBI:31305
CAS Number
10457-90-6
UNII
LYH6F7I22E
DrugBank ID
DB12401
TTD ID
D00SHQ
INTEDE ID
DR0236

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
D(2) dopamine receptor (DRD2) OTBLXKEG DRD2_HUMAN Drug Response [5]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [6]
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS applied to over 900 drugs
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 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.
5 The -141C Ins/Del polymorphism in the dopamine D2 receptor gene promoter region is associated with anxiolytic and antidepressive effects during treatment with dopamine antagonists in schizophrenic patients. Pharmacogenetics. 2001 Aug;11(6):545-50. doi: 10.1097/00008571-200108000-00009.
6 Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
7 Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.