Zuclopenthixol dihydrochlorideProduct ingredient for Zuclopenthixol

Name
Zuclopenthixol dihydrochloride
Drug Entry
Zuclopenthixol

Zuclopenthixol, also known as Zuclopentixol or Zuclopenthixolum, is an antipsychotic agent. Zuclopenthixol is a thioxanthene-based neuroleptic with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors. Major brands of zuclopenthixol are Cisordinol, Acuphase, and Clopixol. This drug is a liquid. This compound belongs to the thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom. Known drug targets of zuclopenthixol include 5-hydroxytryptamine receptor 2A, D(1B) dopamine receptor, D(2) dopamine receptor, D(1A) dopamine receptor, and alpha-1A adrenergic receptor. It is known that zuclopenthixol is metabolized by Cytochrome P450 2D6. Zuclopenthixol was approved for use in Canada in 2011, but is not approved for use in the United States.

Accession Number
DBSALT000546
Structure
Thumb
Synonyms
Zuclopenthixol diHCl / Zuclopenthixol dihydrochloride / Zuclopenthixol hydrochloride
UNII
7042692VYN
CAS Number
58045-23-1
Weight
Average: 473.887
Monoisotopic: 472.090967307
Chemical Formula
C22H27Cl3N2OS
InChI Key
LPWNZMIBFHMYMX-MHKBYHAFSA-N
InChI
InChI=1S/C22H25ClN2OS.2ClH/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;2*1H/b18-5-;;
IUPAC Name
2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol dihydrochloride
SMILES
Cl.Cl.OCCN1CCN(CC\C=C2\C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1
PubChem Compound
6433208
ChemSpider
4938391
ChEMBL
CHEMBL2360084
Predicted Properties
PropertyValueSource
Water Solubility0.0026 mg/mLALOGPS
logP4.46ALOGPS
logP4.22ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127 m3·mol-1ChemAxon
Polarizability45.29 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon