zuclopenthixol ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2877 53772-83-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zuclopenthixol
  • (Z)-Clopenthixol
  • cisordinol
  • clopixol
  • zuclopenthixol dihydrochloride
  • zuclopenthixol hydrochloride
  • zuclopenthixol HCl
Zuclopenthixol is a potent neuroleptic of the thioxanthene series with a piperazine side-chain. The antipsychotic effect of neuroleptics is related to their dopamine receptor blocking effect. The thioxanthenes have a high affinity for both the adenylate cyclase coupled dopamine D1 receptors and for the dopamine D2 receptors; in the phenothiazine group the affinity for D1 receptors is much lower than that for D2 receptors, whereas butyrophenones, diphenylbutylpiperidines and benzamides only have affinity for D2 receptors.
  • Molecular weight: 400.97
  • Formula: C22H25ClN2OS
  • CLOGP: 4.13
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 26.71
  • ALOGS: -5.19
  • ROTB: 5

Drug dosage:

DoseUnitRoute
30 mg O
15 mg P
30 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.56 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 49 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Bocci G, Oprea TI, Benet LZ

Approvals:

DateAgencyCompanyOrphan
None UK Medicines and Healthcare Products Regulatory Agency (MHRA)

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood prolactin abnormal 871.84 53.21 158 4739 2921 63481204
Anosognosia 865.96 53.21 158 4739 3038 63481087
Sexual dysfunction 848.02 53.21 163 4734 4196 63479929
Disturbance in social behaviour 830.84 53.21 158 4739 3835 63480290
Metabolic disorder 782.98 53.21 163 4734 6340 63477785
Personality change 697.47 53.21 150 4747 6823 63477302
Dystonia 580.48 53.21 147 4750 13672 63470453
Sedation 538.92 53.21 174 4723 38635 63445490
Dyskinesia 525.13 53.21 163 4734 31839 63452286
Suicide attempt 465.76 53.21 175 4722 60743 63423382
Blood glucose increased 359.18 53.21 159 4738 83597 63400528
Insurance issue 174.55 53.21 48 4849 6073 63478052
Intentional self-injury 140.15 53.21 58 4839 25629 63458496
Refusal of examination 130.29 53.21 21 4876 182 63483943
Eosinophil count decreased 115.34 53.21 28 4869 2162 63481963
Condition aggravated 104.75 53.21 141 4756 402076 63082049
Schizophrenia 95.77 53.21 34 4863 9918 63474207
Personality change due to a general medical condition 87.22 53.21 15 4882 199 63483926
Drug ineffective 84.61 53.21 221 4676 1044544 62439581
Adverse drug reaction 67.54 53.21 53 4844 79661 63404464
Intentional overdose 66.52 53.21 51 4846 74101 63410024
Electrocardiogram QT prolonged 57.93 53.21 43 4854 59487 63424638
Mean cell haemoglobin decreased 54.81 53.21 19 4878 5160 63478965

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood prolactin abnormal 205.46 36.85 43 4794 926 34951168
Dystonia 200.97 36.85 70 4767 10775 34941319
Anosognosia 199.52 36.85 42 4795 931 34951163
Schizophrenia 184.21 36.85 62 4775 8604 34943490
Disturbance in social behaviour 172.63 36.85 42 4795 1809 34950285
Sexual dysfunction 149.52 36.85 49 4788 6254 34945840
Metabolic disorder 137.73 36.85 42 4795 4241 34947853
Psychotic disorder 136.85 36.85 67 4770 24385 34927709
Delusion of grandeur 132.42 36.85 31 4806 1129 34950965
Personality change 122.07 36.85 40 4797 5099 34946995
Neuroleptic malignant syndrome 118.18 36.85 55 4782 17879 34934215
Sedation 112.87 36.85 56 4781 20950 34931144
Psychotic symptom 91.33 36.85 25 4812 1718 34950376
Dyskinesia 89.56 36.85 49 4788 22364 34929730
Hallucination, auditory 89.35 36.85 40 4797 11877 34940217
Self-injurious ideation 87.52 36.85 24 4813 1660 34950434
Affective disorder 83.99 36.85 29 4808 4331 34947763
Rhinalgia 83.58 36.85 21 4816 1032 34951062
Myocarditis 81.02 36.85 39 4798 13643 34938451
Delusion 80.88 36.85 38 4799 12597 34939497
Extrapyramidal disorder 80.19 36.85 38 4799 12842 34939252
Suicide attempt 71.29 36.85 52 4785 39064 34913030
Aggression 66.96 36.85 50 4787 38914 34913180
Lymphocyte count abnormal 66.57 36.85 18 4819 1180 34950914
Salivary hypersecretion 64.74 36.85 29 4808 8615 34943479
Paranoia 55.53 36.85 29 4808 12039 34940055
Neutrophil count increased 53.72 36.85 32 4805 17114 34934980
Lymphocyte count decreased 50.33 36.85 34 4803 22588 34929506
Hypothermia 49.94 36.85 26 4811 10722 34941372
Patient restraint 49.78 36.85 9 4828 86 34952008
Priapism 48.04 36.85 20 4817 4974 34947120
SARS-CoV-2 test positive 47.94 36.85 21 4816 5912 34946182
Antipsychotic drug level decreased 46.00 36.85 13 4824 1004 34951090
Blepharospasm 44.55 36.85 13 4824 1125 34950969
Nasal discomfort 44.06 36.85 14 4823 1614 34950480
Blood glucose increased 43.87 36.85 50 4787 66668 34885426
Pharyngeal dystonia 38.43 36.85 7 4830 70 34952024

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood prolactin abnormal 947.77 34.90 184 8612 3417 79732175
Anosognosia 933.53 34.90 183 8613 3581 79732011
Disturbance in social behaviour 888.63 34.90 184 8612 4786 79730806
Sexual dysfunction 839.32 34.90 190 8606 7573 79728019
Metabolic disorder 797.32 34.90 188 8608 8982 79726610
Personality change 706.51 34.90 174 8622 9996 79725596
Dystonia 688.04 34.90 199 8597 21200 79714392
Dyskinesia 547.37 34.90 200 8596 44573 79691019
Sedation 536.56 34.90 205 8591 51690 79683902
Suicide attempt 443.80 34.90 205 8591 82727 79652865
Blood glucose increased 341.51 34.90 191 8605 114784 79620808
Schizophrenia 261.28 34.90 88 8708 15352 79720240
Insurance issue 182.50 34.90 53 8743 5680 79729912
Psychotic disorder 136.95 34.90 74 8722 41328 79694264
Delusion of grandeur 132.88 34.90 31 8765 1401 79734191
Neuroleptic malignant syndrome 131.22 34.90 63 8733 27496 79708096
Eosinophil count decreased 128.80 34.90 36 8760 3360 79732232
Refusal of examination 121.27 34.90 21 8775 197 79735395
Delusion 110.49 34.90 51 8745 20372 79715220
Extrapyramidal disorder 105.40 34.90 51 8745 22628 79712964
Hallucination, auditory 100.61 34.90 48 8748 20645 79714947
Drug ineffective 99.84 34.90 302 8494 1080611 78654981
Psychotic symptom 95.06 34.90 27 8769 2670 79732922
Adverse drug reaction 91.07 34.90 68 8728 66324 79669268
Electrocardiogram QT prolonged 88.59 34.90 76 8720 90310 79645282
Intentional self-injury 85.59 34.90 50 8746 32369 79703223
Salivary hypersecretion 84.76 34.90 38 8758 14186 79721406
Aggression 83.15 34.90 58 8738 50900 79684692
Leukopenia 75.75 34.90 78 8718 116435 79619157
Affective disorder 72.11 34.90 29 8767 8290 79727302
Rhinalgia 71.42 34.90 21 8775 2346 79733246
Condition aggravated 71.41 34.90 165 8631 500959 79234633
Personality change due to a general medical condition 67.48 34.90 13 8783 229 79735363
Lymphocyte count abnormal 66.56 34.90 18 8778 1485 79734107
Self-injurious ideation 62.54 34.90 21 8775 3617 79731975
Mental impairment 60.06 34.90 33 8763 19003 79716589
Pain 59.22 34.90 5 8791 703797 79031795
Myocarditis 58.62 34.90 34 8762 21699 79713893
Priapism 54.42 34.90 20 8776 4485 79731107
Neutropenia 52.68 34.90 105 8691 287605 79447987
Mean cell haemoglobin decreased 51.54 34.90 21 8775 6203 79729389
Arthralgia 51.14 34.90 3 8793 571800 79163792
Patient restraint 50.92 34.90 9 8787 96 79735496
Mean cell haemoglobin concentration decreased 50.45 34.90 19 8777 4560 79731032
Dyspnoea 48.71 34.90 17 8779 857008 78878584
Lymphocyte count decreased 44.74 34.90 39 8757 47250 79688342
Neutrophil count increased 44.55 34.90 32 8764 29364 79706228
Paranoia 43.58 34.90 27 8769 19405 79716187
Schizoaffective disorder 43.33 34.90 14 8782 2138 79733454
Agitation 43.03 34.90 54 8742 99661 79635931
Persecutory delusion 42.15 34.90 17 8779 4892 79730700
Nausea 42.12 34.90 27 8769 957169 78778423
Hypothermia 39.69 34.90 27 8769 22719 79712873
Rash 39.36 34.90 8 8788 578350 79157242
Psychomotor hyperactivity 39.29 34.90 24 8772 16825 79718767
Suicidal ideation 38.92 34.90 45 8751 76295 79659297
SARS-CoV-2 test positive 38.86 34.90 21 8775 11695 79723897
Pneumonia 37.63 34.90 13 8783 660233 79075359
Antipsychotic drug level decreased 37.55 34.90 11 8785 1213 79734379
Serositis 36.70 34.90 10 8786 848 79734744

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AF05 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Thioxanthene derivatives
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:37890 alpha-adrenergic receptor blockaders
CHEBI has role CHEBI:37955 H1 receptor antagonists
CHEBI has role CHEBI:48279 serotonin antagonists
CHEBI has role CHEBI:48561 dopaminergic antagonists
CHEBI has role CHEBI:65190 typical antipsychotic drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.19 Basic
pKa2 4.19 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(1A) dopamine receptor GPCR ANTAGONIST WOMBAT-PK DRUG LABEL
D(2) dopamine receptor GPCR ANTAGONIST WOMBAT-PK DRUG LABEL
5-hydroxytryptamine receptor 2A GPCR WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 6.77 CHEMBL
Alpha-1A adrenergic receptor GPCR WOMBAT-PK

External reference:

IDSource
D03556 KEGG_DRUG
C0376160 UMLSCUI
CHEBI:51364 CHEBI
CHEMBL53904 ChEMBL_ID
D003006 MESH_DESCRIPTOR_UI
DB01624 DRUGBANK_ID
5311507 PUBCHEM_CID
7559 IUPHAR_LIGAND_ID
5443 INN_ID
58045-23-1 SECONDARY_CAS_RN
47ISU063SG UNII
DB13841 DRUGBANK_ID
102546 RXNORM
004069 NDDF
004072 NDDF
387566002 SNOMEDCT_US
426594007 SNOMEDCT_US
427940003 SNOMEDCT_US
428715002 SNOMEDCT_US
429346008 SNOMEDCT_US
C0009026 UMLSCUI
1315 INN_ID

Pharmaceutical products:

None