CHEBI:9566 - thioridazine

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ChEBI Name thioridazine
ChEBI ID CHEBI:9566
Definition A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H26N2S2
Net Charge 0
Average Mass 370.57500
Monoisotopic Mass 370.154
InChI InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChIKey KLBQZWRITKRQQV-UHFFFAOYSA-N
SMILES CSc1ccc2Sc3ccccc3N(CCC3CCCCN3C)c2c1
Roles Classification
Biological Role(s): 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).
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12).
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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.
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.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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.
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 thioridazine (CHEBI:9566) has part methylsulfanyl group (CHEBI:48563)
thioridazine (CHEBI:9566) has role α-adrenergic antagonist (CHEBI:37890)
thioridazine (CHEBI:9566) has role dopaminergic antagonist (CHEBI:48561)
thioridazine (CHEBI:9566) has role EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (CHEBI:77402)
thioridazine (CHEBI:9566) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
thioridazine (CHEBI:9566) has role first generation antipsychotic (CHEBI:65190)
thioridazine (CHEBI:9566) has role H1-receptor antagonist (CHEBI:37955)
thioridazine (CHEBI:9566) has role serotonergic antagonist (CHEBI:48279)
thioridazine (CHEBI:9566) is a phenothiazines (CHEBI:38093)
thioridazine (CHEBI:9566) is a piperidines (CHEBI:26151)
Incoming thioridazine hydrochloride (CHEBI:48566) has part thioridazine (CHEBI:9566)
IUPAC Name
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine
INNs Sources
thioridazine ChemIDplus
thioridazinum ChemIDplus
tioridazina ChemIDplus
Synonyms Sources
10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulfanyl-phenothiazine IUPHAR
2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine ChemIDplus
3-Methylmercapto-N-(2'-(N-methyl-2-piperidyl)ethyl)phenothiazine ChemIDplus
Thioridazin DrugBank
Brand Names Sources
Mallorol DrugBank
Malloryl IUPHAR
Meleril DrugBank
Mellaril DrugBank
Mellaril-S KEGG DRUG
Mellerets IUPHAR
Mellerette DrugBank
Melleril DrugBank
Orsanil DrugBank
Sonapax DrugBank
Database Links Databases
2637 DrugCentral
D00373 KEGG DRUG
DB00679 DrugBank
HMDB0014817 HMDB
LSM-1863 LINCS
Thioridazine Wikipedia
View more database links
Registry Numbers Types Sources
50-52-2 CAS Registry Number ChemIDplus
94457 Reaxys Registry Number Reaxys
94457 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10796547 PubMed citation Europe PMC
11686961 PubMed citation Europe PMC
1650428 PubMed citation Europe PMC
17764469 PubMed citation Europe PMC
17876580 PubMed citation Europe PMC
19747949 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
26956010 PubMed citation Europe PMC
27023487 PubMed citation Europe PMC
27068340 PubMed citation Europe PMC
9352572 PubMed citation Europe PMC
Last Modified
22 February 2017