CHEBI:59115 - clopenthixol

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ChEBI Name clopenthixol
ChEBI ID CHEBI:59115
Definition A thioxanthene derivative having a chloro substituent at the 2-position and an alkylidene group at the 10-position with undefined double bond stereochemistry.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5875452, ZINC000000010402
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Promazine (brand name Sparine among others), is used as a short-term add-on treatment for psychomotor agitation. Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine. It has weak antipsychotic effects but is generally not used to treat psychoses. It acts similar to chlorpromazine and causes sedation. It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon. It belongs to the typical antipsychotic and phenothiazine class of drugs. Promazine was approved for medical use in the United States in the 1950s, although it is no longer commercially available there.
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Formula C22H25ClN2OS
Net Charge 0
Average Mass 400.96500
Monoisotopic Mass 400.13761
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
InChIKey WFPIAZLQTJBIFN-UHFFFAOYSA-N
SMILES [H]C(CCN1CCN(CCO)CC1)=C1c2ccccc2Sc2ccc(Cl)cc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
Application(s): first generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be more likely than second generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements; such body movements can become permanent even after treatment has ceased.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
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ChEBI Ontology
Outgoing clopenthixol (CHEBI:59115) has role α-adrenergic antagonist (CHEBI:37890)
clopenthixol (CHEBI:59115) has role dopaminergic antagonist (CHEBI:48561)
clopenthixol (CHEBI:59115) has role first generation antipsychotic (CHEBI:65190)
clopenthixol (CHEBI:59115) has role H1-receptor antagonist (CHEBI:37955)
clopenthixol (CHEBI:59115) has role serotonergic antagonist (CHEBI:48279)
clopenthixol (CHEBI:59115) is a N-alkylpiperazine (CHEBI:46845)
clopenthixol (CHEBI:59115) is a primary alcohol (CHEBI:15734)
clopenthixol (CHEBI:59115) is a thioxanthenes (CHEBI:50930)
Incoming zuclopenthixol (CHEBI:51364) is a clopenthixol (CHEBI:59115)
IUPAC Name
2-{4-[3-(2-chloro-9H-thioxanthen-9-ylidene)propyl]piperazin-1-yl}ethan-1-ol
INNs Sources
clopenthixolum ChemIDplus
clopentixol ChemIDplus
Synonyms Sources
2-{4-[3-(2-chloro-10H-dibenzo[b,e]thiopyran-10-ylidene)propyl]piperazin-1-yl}ethanol IUPAC
4-(3-(2-Chloro-9H-thioxanthen-9-ylidene)propyl)-1-piperazineethanol ChemIDplus
4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol ChemIDplus
Chlorpenthixol ChemIDplus
Manual Xrefs Databases
4397 DrugCentral
BE585338 Patent
Clopenthixol Wikipedia
D02613 KEGG DRUG
LSM-2631 LINCS
US3116291 Patent
View more database links
Registry Numbers Types Sources
899403 Beilstein Registry Number Beilstein
982-24-1 CAS Registry Number ChemIDplus
982-24-1 CAS Registry Number KEGG DRUG
Citation Type Source
1650428 PubMed citation Europe PMC
Last Modified
22 February 2017