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Identification
NameZuclopenthixol
Accession NumberDB01624  (DB08919, DB08920)
TypeSmall Molecule
GroupsApproved, Investigational
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
cis-ClopenthixolNot AvailableIS
ZuclopenthixolumLatinINN
ZuclopentixolSpanishINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AcuphaseH. Lundbeck A/S
Ciatyl-ZBayer Vital
CisordinolH. Lundbeck A/S
ClopixolH. Lundbeck A/S
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Zuclopenthixol acetate
Thumb
  • InChI Key: OXAUOBQMCDIVPQ-IOXNKQMXSA-N
  • Monoisotopic Mass: 442.148176515
  • Average Mass: 443.001
DBSALT000545
Zuclopenthixol decanoate
64053-00-5
Thumb
  • InChI Key: QRUAPADZILXULG-WKIKZPBSSA-N
  • Monoisotopic Mass: 554.273377027
  • Average Mass: 555.214
DBSALT000787
Zuclopenthixol dihydrochloride
Thumb
  • InChI Key: LPWNZMIBFHMYMX-MHKBYHAFSA-N
  • Monoisotopic Mass: 472.090967307
  • Average Mass: 473.887
DBSALT000546
Categories
CAS number53772-83-1
WeightAverage: 400.965
Monoisotopic: 400.137611829
Chemical FormulaC22H25ClN2OS
InChI KeyWFPIAZLQTJBIFN-DVZOWYKESA-N
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-
IUPAC Name
2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
SMILES
OCCN1CCN(CC\C=C2\C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1
Taxonomy
DescriptionThis compound 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
  • N-alkylpiperazine
  • Chlorobenzene
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Azacycle
  • Thioether
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed in the management of acute psychoses such as mania or schizophrenia. However, the use of zuclopenthixol acetate in psychiatric emergencies as an alternative to standard treatments (haloperidol, clotiapine, etc.) should be cautioned, since well executed and documented trials of zuclopenthixol acetate for this use have yet to be conducted. Zuclopenthixol acetate is not intended for long-term use.
PharmacodynamicsZuclopenthixol is a thioxanthene with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors.
Mechanism of actionZuclopenthixol is a typical antipsychotic neuroleptic drug of the thioxanthene class. It mainly acts by antagonism of D1 and D2 dopamine receptors. Zuclopenthixol also has high affinity for alpha1-adrenergic and 5-HT2 receptors. It has weaker histamine H1 receptor blocking activity, and even lower affinity for muscarinic cholinergic and alpha2-adrenergic receptors.
AbsorptionUpon reaching the body water phase, the decanoate ester is slowly released from the oil depot, which is resultantly hydrolyzed to the active substance, zuclopenthixol. The decanoate ester provides a means of slow release since zuclopenthixol itself is a short-acting drug.
Volume of distribution

20 L/kg.

Protein binding98-99%
Metabolism

The metabolism of zuclopenthixol is mainly by sulphoxidation, side chain N-dealkylation and glucuronic acid conjugation. The metabolites are devoid of pharmacological activity.

Route of eliminationPrimarily in the feces with approximately 10% in the urine.
Half life20 hours (range 12-28 hours) for the tablet form, 19 days for the depot form.
Clearance

approximately 0.9 L/min.

ToxicityAlthough there have not been any cases of overdosage reported, the symptoms are likely to be somnolence, coma, extrapyramidal symptoms, convulsions, hypotension, shock, or hyper- or hypothermia. Neuroleptic malignant syndrome may occur. Zuclopenthixol may potentiate anticholinergic effects of concurrent medications. Zuclopenthixol has a demonstrated antiemetic effect in animals, and may mask signs of toxicity due to other drug overdoses, or may mask symptoms of disease.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9443
Blood Brain Barrier+0.9676
Caco-2 permeable-0.5313
P-glycoprotein substrateSubstrate0.8762
P-glycoprotein inhibitor IInhibitor0.8736
P-glycoprotein inhibitor IIInhibitor0.7439
Renal organic cation transporterInhibitor0.5829
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6722
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateInhibitor0.8931
CYP450 2C19 substrateInhibitor0.7518
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8213
Ames testNon AMES toxic0.7617
CarcinogenicityNon-carcinogens0.9029
BiodegradationNot ready biodegradable0.9954
Rat acute toxicity2.8877 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6099
hERG inhibition (predictor II)Inhibitor0.7023
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Clopixol Acuphase 50 mg/ml16.52USD ml
Clopixol Depot 200 mg/ml16.52USD ml
Clopixol 25 mg Tablet1.06USD tablet
Clopixol 10 mg Tablet0.42USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point~50http://www.lundbeck.com/upload/ca/en/files/pdf/product_monograph/Clopixol_PM_MKT_ctrl_148975_13SEPT2011_CLN_eng.pdf
water solubilityslighthttp://www.lundbeck.com/upload/ca/en/files/pdf/product_monograph/Clopixol_PM_MKT_ctrl_148975_13SEPT2011_CLN_eng.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.0026 mg/mLALOGPS
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 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (140 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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. Pubmed
  2. 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. 2013 Jun 15. Pubmed
  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. Pubmed
  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. Pubmed
  5. 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. Pubmed
  6. Hood S, Orr K, Bennett L, Davies S: Severe laryngeal dystonia in a patient receiving zuclopenthixol “Acuphase” and fluoxetine. Australas Psychiatry. 2010 Apr;18(2):174-6. doi: 10.3109/10398560903473686. Pubmed
  7. http://medicaid.alabama.gov/documents/2.0_Newsroom/2.4_Procurement/2.4.3_Pharm_Support_ITB/2.4.3_Antipsychotic_Agents_Class_Review_8-10-11.pdf
  8. http://www.mentalhealth.com/drug/p30-z03.html
External Links
ATC CodesN05AF05
AHFS Codes
  • 281608
PDB EntriesNot Available
FDA labelDownload (229 KB)
MSDSDownload (568 KB)
Interactions
Drug Interactions
Drug
AclidiniumMay enhance the anticholinergic effect of Anticholinergic Agents.
AlmotriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AmisulprideAntipsychotic Agents may enhance the adverse/toxic effect of Amisulpride.
AmitriptylineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AmoxapineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AmphetamineMay diminish the stimulatory effect of Amphetamines.
AprepitantCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
AtazanavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
BenzphetamineMay diminish the stimulatory effect of Amphetamines.
BicalutamideCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
BiotinCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
BoceprevirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
BuprenorphineCNS Depressants may enhance the CNS depressant effect of Buprenorphine.
BuspironeSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
CabergolineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
CarbamazepineCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
CathinoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
CimetidineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
CitalopramSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ClomipramineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ClotrimazoleCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
ConivaptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
CyclobenzaprineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DarunavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
DelavirdineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
DesipramineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DesvenlafaxineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DextroamphetamineMay diminish the stimulatory effect of Amphetamines.
DextromethorphanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DihydroergotamineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DiltiazemCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
DonepezilAcetylcholinesterase Inhibitors (Central) may enhance the neurotoxic (central) effect of Antipsychotic Agents. Severe extrapyramidal symptoms have occurred in some patients.
DoxylamineMay enhance the CNS depressant effect of CNS Depressants.
DronabinolMay enhance the CNS depressant effect of CNS Depressants.
DuloxetineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
EletriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
EnzalutamideCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
Ergoloid mesylateSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ErgonovineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ErgotamineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
EscitalopramSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FentanylSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FluoxetineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FluvoxamineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FosamprenavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
FosaprepitantCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
FrovatriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
GalantamineAcetylcholinesterase Inhibitors (Central) may enhance the neurotoxic (central) effect of Antipsychotic Agents. Severe extrapyramidal symptoms have occurred in some patients.
HydrocodoneCNS Depressants may enhance the CNS depressant effect of Hydrocodone.
ImipramineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
IndinavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
IsavuconazoniumCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
IsocarboxazidSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ItoprideAnticholinergic Agents may diminish the therapeutic effect of Itopride.
ItraconazoleCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
LevomilnacipranSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
LinezolidSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
LisdexamfetamineMay diminish the stimulatory effect of Amphetamines.
LithiumLithium may enhance the neurotoxic effect of Antipsychotic Agents. Lithium may decrease the serum concentration of Antipsychotic Agents. Specifically noted with chlorpromazine.
LomitapideCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
LorcaserinSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
Magnesium SulfateMay enhance the CNS depressant effect of CNS Depressants.
MaprotilineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MethadoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MethamphetamineMay diminish the stimulatory effect of Amphetamines.
MethotrimeprazineCNS Depressants may enhance the CNS depressant effect of Methotrimeprazine. Methotrimeprazine may enhance the CNS depressant effect of CNS Depressants.
MethylergometrineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MethylphenidateMay enhance the adverse/toxic effect of Methylphenidate. Methylphenidate may enhance the adverse/toxic effect of Antipsychotic Agents.
MetoclopramideMetoclopramide may enhance the adverse/toxic effect of Antipsychotic Agents.
MetyrosineMetyrosine may enhance the adverse/toxic effect of Antipsychotic Agents.
MifepristoneMay enhance the QTc-prolonging effect of Highest Risk QTc-Prolonging Agents.
MilnacipranSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MoclobemideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
NabiloneMay enhance the CNS depressant effect of CNS Depressants.
NaratriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
NefazodoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
NelfinavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
NortriptylineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
OrphenadrineCNS Depressants may enhance the CNS depressant effect of Orphenadrine.
ParoxetineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
Peginterferon alfa-2bMay decrease the serum concentration of CYP2D6 Substrates. Peginterferon Alfa-2b may increase the serum concentration of CYP2D6 Substrates.
PerampanelMay enhance the CNS depressant effect of CNS Depressants.
PethidineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PhendimetrazineMay diminish the stimulatory effect of Amphetamines.
PhenelzineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PhenobarbitalCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
PhentermineMay diminish the stimulatory effect of Amphetamines.
PhenytoinCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
PosaconazoleCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
Potassium ChlorideAnticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
PramlintideMay enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
PrimidoneCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
ProcarbazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PromethazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ProtriptylineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RasagilineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RifampicinCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
RifapentineCYP3A4 Inducers (Strong) may decrease the serum concentration of Zuclopenthixol.
RitonavirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
RivastigmineAcetylcholinesterase Inhibitors (Central) may enhance the neurotoxic (central) effect of Antipsychotic Agents. Severe extrapyramidal symptoms have occurred in some patients.
RizatriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RufinamideMay enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
SecretinAnticholinergic Agents may diminish the therapeutic effect of Secretin.
SelegilineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
SertralineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
SulpirideAntipsychotic Agents may enhance the adverse/toxic effect of Sulpiride.
SumatriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
SuvorexantCNS Depressants may enhance the CNS depressant effect of Suvorexant.
TapentadolMay enhance the CNS depressant effect of CNS Depressants.
Tedizolid PhosphateSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TelaprevirCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
TetrabenazineTetrabenazine may enhance the adverse/toxic effect of Antipsychotic Agents.
TetracyclineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
ThalidomideCNS Depressants may enhance the CNS depressant effect of Thalidomide.
TiotropiumAnticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
TopiramateAnticholinergic Agents may enhance the adverse/toxic effect of Topiramate.
TramadolSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TranylcypromineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TrimipramineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
VenlafaxineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
VilazodoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ZolmitriptanSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ZolpidemCNS Depressants may enhance the CNS depressant effect of Zolpidem.
Food InteractionsNot Available

Targets

1. D(1A) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details

References:

  1. Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. Pubmed
  2. Manzaneque JM, Navarro JF: 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. Pubmed

2. D(1B) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1B) dopamine receptor P21918 Details

References:

  1. Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. Pubmed
  2. Manzaneque JM, Navarro JF: 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. Pubmed

3. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Gareri P, De Fazio P, Stilo M, Ferreri G, De Sarro G: Conventional and Atypical Antipsychotics in the Elderly : A Review. Clin Drug Investig. 2003;23(5):287-322. Pubmed
  2. Lublin H, Gerlach J, Hagert U, Meidahl B, Molbjerg C, Pedersen V, Rendtorff C, Tolvanen E: Zuclopenthixol, a combined dopamine D1/D2 antagonist, versus haloperidol, a dopamine D2 antagonist, in tardive dyskinesia. Eur Neuropsychopharmacol. 1991 Dec;1(4):541-8. Pubmed
  3. Nyberg S, Farde L, Bartfai A, Halldin C: Central D2 receptor occupancy and effects of zuclopenthixol acetate in humans. Int Clin Psychopharmacol. 1995 Nov;10(4):221-7. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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. Pubmed

5. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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. Pubmed

6. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Nyberg S, Farde L, Bartfai A, Halldin C: Central D2 receptor occupancy and effects of zuclopenthixol acetate in humans. Int Clin Psychopharmacol. 1995 Nov;10(4):221-7. Pubmed
  2. Gjerden P, Slordal L, Bramness JG: Association between the use of anticholinergic antiparkinson drugs and safety and receptor drug-binding profiles of antipsychotic agents. Eur J Clin Pharmacol. 2009 Jul 31. Pubmed
  3. Khalifa AE: Zuclopenthixol facilitates memory retrieval in rats: possible involvement of noradrenergic and serotonergic mechanisms. Pharmacol Biochem Behav. 2003 Jul;75(4):755-62. Pubmed

7. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

http://www.lundbeck.com/upload/ca/en/files/pdf/product_monograph/Clopixol_PM_MKT_ctrl_148975_13SEPT2011_CLN_eng.pdf


Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on August 29, 2007 14:18 / Updated on November 24, 2014 14:45