Details of the Drug

General Information of Drug (ID: DMKYD5N)

Drug Name
Zuclopenthixol
Synonyms
Acuphase; CLOPENTHIXOL; Cisordinol; Clopenthixolum; Clopentixol; Clopixol; Zuclopenthixolum; Zuclopentixol; Alpha Clopenthixol; Zuclopenthixolum [Latin]; Zuclopentixol [Spanish]; Acuphase (TN); Alpha-Clopenthixol; Cisordinol (TN); Clopenthixol (USAN); Clopixol (TN); Zuclopenthixol (INN); Zuclopenthixol [BAN:INN]; (Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol; 2-[4-[(3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol; 2-{4-[(3Z)-3-(2-chloro-10H-dibenzo[b,e]thiopyran-10-ylidene)propyl]piperazin-1-yl}ethanol; 2-{4-[3-(2-chloro-10H-dibenzo[b,e]thiopyran-10-ylidene)propyl]piperazin-1-yl}ethanol; 4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Approved [1]
Therapeutic Class
Antipsychotic Agents
Affected Organisms
Humans and other mammals
ATC Code
N05AF02: Zuclopenthixol
N05AF: Thioxanthene derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AF02: Zuclopenthixol
N05AF: Thioxanthene derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AF05: Zuclopenthixol
N05AF: Thioxanthene derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AF05: Zuclopenthixol
N05AF: Thioxanthene derivatives
N05A: ANTIPSYCHOTICS
N05: PSYCHOLEPTICS
N: NERVOUS SYSTEM
N05AF05: Zuclopenthixol
N05AF: Thioxanthene 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) 401
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Clearance
The clearance of drug is approximately 0.9 L/min []
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours [2]
Metabolism
The drug is metabolized via sulphoxidation []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.56275 micromolar/kg/day [3]
Vd
The volume of distribution (Vd) of drug is 20 L/kg []
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Tardive dyskinesia Not Available DRD2 OTBLXKEG [4]
Tardive dyskinesia Not Available DRD3 OT0OFFKB [4]
Tardive dyskinesia Not Available DRD4 OTAJTO7N [4]
Chemical Identifiers
Formula
C22H25ClN2OS
IUPAC Name
2-[4-[(3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol
Canonical SMILES
C1CN(CCN1CC/C=C\\2/C3=CC=CC=C3SC4=C2C=C(C=C4)Cl)CCO
InChI
InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-
InChIKey
WFPIAZLQTJBIFN-DVZOWYKESA-N
Cross-matching ID
PubChem CID
5311507
ChEBI ID
CHEBI:51364
CAS Number
53772-83-1
UNII
47ISU063SG
DrugBank ID
DB01624
TTD ID
D0I8LU
INTEDE ID
DR1741
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD 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 Antagonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
D(2) dopamine receptor (DRD2) OTBLXKEG DRD2_HUMAN Drug Response [4]
D(3) dopamine receptor (DRD3) OT0OFFKB DRD3_HUMAN Drug Response [4]
D(4) dopamine receptor (DRD4) OTAJTO7N DRD4_HUMAN Drug Response [4]
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

Molecular Expression Atlas of This Drug

The Studied Disease Schizophrenia
ICD Disease Classification 6A20
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
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.30E-01 -1.91E-02 -1.41E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7559).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5 An ethopharmacological assessment of the effects of zuclopenthixol on agonistic interactions in male mice. Methods Find Exp Clin Pharmacol. 1999 Jan-Feb;21(1):11-5.
6 Genotype and co-medication dependent CYP2D6 metabolic activity: effects on serum concentrations of aripiprazole, haloperidol, risperidone, paliperidone and zuclopenthixol. Eur J Clin Pharmacol. 2016 Feb;72(2):175-84.
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.