CHEBI:5121 - flupenthixol

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ChEBI Name flupenthixol
ChEBI ID CHEBI:5121
Definition A thioxanthene derivative having a trifluoromethyl substituent at the 2-position and a 3-(4-(2-hydroxyethyl)piperazin-1-yl)propylidene group at the 10-position with undefined double bond stereochemistry.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H27F3N2OS
Net Charge 0
Average Mass 436.53300
Monoisotopic Mass 436.17962
InChI InChI=1S/C23H27F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,20,22,29H,3,9-15H2
InChIKey DTTVNHWDONBIKE-UHFFFAOYSA-N
SMILES [H]C(CCN1CCN(CCO)CC1)=C1C2C=C(C=CC2Sc2ccccc12)C(F)(F)F
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): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous 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.
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
Application(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous 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.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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.
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ChEBI Ontology
Outgoing flupenthixol (CHEBI:5121) has role α-adrenergic antagonist (CHEBI:37890)
flupenthixol (CHEBI:5121) has role antidepressant (CHEBI:35469)
flupenthixol (CHEBI:5121) has role anxiolytic drug (CHEBI:35474)
flupenthixol (CHEBI:5121) has role dopaminergic antagonist (CHEBI:48561)
flupenthixol (CHEBI:5121) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
flupenthixol (CHEBI:5121) has role first generation antipsychotic (CHEBI:65190)
flupenthixol (CHEBI:5121) is a N-alkylpiperazine (CHEBI:46845)
flupenthixol (CHEBI:5121) is a fluorine molecular entity (CHEBI:24062)
flupenthixol (CHEBI:5121) is a primary alcohol (CHEBI:15734)
flupenthixol (CHEBI:5121) is a thioxanthenes (CHEBI:50930)
IUPAC Name
2-(4-{3-[2-(trifluoromethyl)-4a,9a-dihydro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethanol
INNs Sources
flupentixol WHO MedNet
flupentixol ChemIDplus
Synonyms Sources
2-Trifluoromethyl-9-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propylidene)thioxanthene ChemIDplus
2-Trifluoromethyl-9-(3-(4-(beta-hydroxyethyl)-1-piperazinyl)propylidene)thioxanthene ChemIDplus
4-(3-(2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)-1-piperazineethanol ChemIDplus
4-(3-(2-(Trifluoromethyl)thioxanthen-9-ylidene)propyl)-1-piperazineethanol ChemIDplus
flupentixolum WHO MedNet
Manual Xrefs Databases
D01044 KEGG DRUG
DB00875 DrugBank
Flupentixol Wikipedia
GB925538 Patent
US3282930 Patent
US3681346 Patent
View more database links
Registry Number Type Source
2709-56-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1650428 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
26945819 PubMed citation Europe PMC
8826544 PubMed citation Europe PMC
9682999 PubMed citation Europe PMC
Last Modified
31 May 2016