Zuclopenthixol (CED0006708)

Record Information
Version1.0
Creation Date2016-05-25 18:28:32 UTC
Update Date2026-08-21 22:19:04 UTC
Accession NumberCHEM022332
Identification
Common NameZuclopenthixol
ClassSmall Molecule
Description
Zuclopenthixol is an organic compound with the chemical formula $\text{C}_{22}\text{H}_{25}\text{ClN}_2\text{OS}$ and an average molecular weight of 400.96 g/mol. Zuclopenthixol belongs to the 1-benzothiopyrans, a subclass of benzothiopyrans within the organic compounds. The compound is associated with two recorded sources: pharmaceuticals and veterinary products, specifically antipsychotics, and household cleaning and consumer products, specifically non-electric simulated smoking devices. Recorded exposure routes for the substance include oral and intramuscular administration. Zuclopenthixol interacts with seven recorded protein targets. It acts as an antagonist of the $\text{D}(1\text{A})$ dopamine receptor ($\text{DRD1}$), the $\text{D}(1\text{B})$ dopamine receptor ($\text{DRD5}$), the $\text{D}(2)$ dopamine receptor ($\text{DRD2}$), and the Alpha-1A adrenergic receptor ($\text{ADRA1A}$), in addition to three other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanolChEBI
ZuclopenthixolumChEBI
ZuclopentixolChEBI
ClopixolKegg
Zuclopenthixol acetateHMDB
Zuclopenthixol decanoateHMDB
Zuclopenthixol dihydrochlorideHMDB
alpha ClopenthixolHMDB
alpha-ClopenthixolHMDB
ClopenthixolHMDB
CisordinolHMDB
Chemical FormulaC22H25ClN2OS
Average Molecular Mass400.965 g/mol
Monoisotopic Mass400.138 g/mol
CAS Registry Number53772-83-1
IUPAC Name2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
Traditional Namezuclopenthixol
SMILESOCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1
InChI IdentifierInChI=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-
InChI KeyWFPIAZLQTJBIFN-DVZOWYKESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiopyrans
Sub Class1-benzothiopyrans
Direct ParentThioxanthenes
Alternative Parents
Substituents
  • Thioxanthene
  • Diarylthioether
  • Aryl thioether
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Azacycle
  • Thioether
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP4.46ALOGPS
logP4.22ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127 m³·mol⁻¹ChemAxon
Polarizability45.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0007-9634000000-725d867abc3a21a8367bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0gi0-9344200000-75820d187d1501e996b0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0122900000-b0c208380aecf467bf42Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fl0-3797300000-6a0d6b81802987061025Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-022j-9742000000-32dbb76748579ce3b574Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-111f43ef21dddab4b92aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1309000000-5ad402c11e1d57ff2c3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-4957e4a977f2522244e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0000900000-c8fc2efcbee8e9787417Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-0173900000-88227a1c47ee94c13262Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0c00-1498000000-7582c437e09f5a3c3e63Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-f42087d0e1f36c98fd92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-0009000000-de6822a024bc2597f5b7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-1059000000-01d717517b320d6b747fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
241.0Log mg/kg[140:430]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
374AntipsychoticsHealthcare, pharmaceuticals & veterinary productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
Pathways
6 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)7.47353
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)12.5337
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)11.9888
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)93.4969
Click to view 3D structurePleiotropic ABC efflux transporter of multiple drugsP33302Saccharomyces cerevisiae S288cPredicted (SEA)1.01204
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)37.0562
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)48.2665
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)92.1735
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)45.3861
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)33.4752
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)202.019
D(1B) dopamine receptor structureClick to view 3D structureD(1B) dopamine receptorP21918HumansPredicted (SEA)41.7272
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)103.773
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)143.71
Potassium channel subfamily K member 2 structureClick to view 3D structurePotassium channel subfamily K member 2O95069HumansPredicted (SEA)0.155698
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)209.57
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)134.212
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)196.336
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)115.995
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)43.9848
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)132.499
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)56.285
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)98.2457
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)53.0932
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)48.4222
Concentrations
Not Available
External Links
DrugBank IDDB01624
HMDB IDHMDB0015561
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZuclopenthixol
Chemspider ID4470984
ChEBI ID51364
PubChem Compound ID5311507
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62.
2. Khalifa AE: Pro-oxidant activity of zuclopenthixol in vivo: differential effect of the drug on brain oxidative status of scopolamine-treated rats. Hum Exp Toxicol. 2004 Aug;23(9):439-45.
3. Jayakody K, Gibson RC, Kumar A, Gunadasa S: Zuclopenthixol acetate for acute schizophrenia and similar serious mental illnesses. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD000525. doi: 10.1002/14651858.CD000525.pub3.
4. Nielsen MK, Johansen SS: Simultaneous determination of 25 common pharmaceuticals in whole blood using ultra-performance liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Sep;36(7):497-506. doi: 10.1093/jat/bks054. Epub 2012 Jun 19.
5. Fond G, Macgregor A, Tamouza R, Hamdani N, Meary A, Leboyer M, Dubremetz JF: Comparative analysis of anti-toxoplasmic activity of antipsychotic drugs and valproate. Eur Arch Psychiatry Clin Neurosci. 2014 Mar;264(2):179-83. doi: 10.1007/s00406-013-0413-4. Epub 2013 Jun 15.
6. Internet Mental Health: http://www.mentalhealth.com/drug/p30-z03.html#Head_7