Details of the Drug

General Information of Drug (ID: DM2AOTZ)

Drug Name
Perazine
Synonyms
Perazine maleate; Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, maleate; 84-97-9 (Parent); 10H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, (Z)-2-butenedioate; SCHEMBL220704; AC1O6123; LS-105593; 10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
Indication
Disease Entry ICD 11 Status REF
Psychotic disorder 6A20-6A25 Approved [1]
ATC Code
N05AB10: Perazine
N05AB: Phenothiazines with piperazine structure
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AB10: Perazine
N05AB: Phenothiazines with piperazine structure
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 339.5
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C20H25N3S
IUPAC Name
10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
Canonical SMILES
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
InChI
InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3
InChIKey
WEYVCQFUGFRXOM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4744
ChEBI ID
CHEMBL1697766
CAS Number
84-97-9
UNII
8915147A2B
DrugBank ID
DB12710
TTD ID
D07JWT
VARIDT ID
DR01265
INTEDE ID
DR1258
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [4]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Flavin-containing monooxygenase 3 (FMO3) OT1G2EV3 FMO3_HUMAN Biotransformations [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Psychotic disorder
ICD Disease Classification 6A20-6A25
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
Cytochrome P450 2E1 (CYP2E1) DME CYP2E1 1.87E-04 -1.20E-01 -3.22E-01
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 2.02E-01 -2.49E-02 -1.81E-01
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 7.36E-01 1.62E-02 1.08E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 2.40E-01 -3.31E-02 -1.97E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.30E-01 -1.91E-02 -1.41E-01
Cytochrome P450 1A1 (CYP1A1) DME CYP1A1 6.83E-06 -1.42E-01 -4.93E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.90E-01 -9.81E-03 -5.96E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005 Jan 3;13(1):77-87.
3 Identification of P-glycoprotein substrates and inhibitors among psychoactive compounds--implications for pharmacokinetics of selected substrates. J Pharm Pharmacol. 2004 Aug;56(8):967-75.
4 The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes. Eur Neuropsychopharmacol. 2004 May;14(3):199-208.
5 Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. Pol J Pharmacol. 2001 Nov-Dec;53(6):615-21.
6 Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro. Psychopharmacology (Berl). 2000 Sep;151(4):312-20.
7 Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4. Pol J Pharmacol. 2002 Jul-Aug;54(4):407-10.