CHEBI:6780 - mesoridazine

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ChEBI Name mesoridazine
ChEBI ID CHEBI:6780
Definition A phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:248004
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Formula C21H26N2OS2
Net Charge 0
Average Mass 386.57400
Monoisotopic Mass 386.149
InChI InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChIKey SLVMESMUVMCQIY-UHFFFAOYSA-N
SMILES CN1CCCCC1CCN1c2ccccc2Sc2ccc(cc12)S(C)=O
Roles Classification
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.
Application(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
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 mesoridazine (CHEBI:6780) has role dopaminergic antagonist (CHEBI:48561)
mesoridazine (CHEBI:6780) has role first generation antipsychotic (CHEBI:65190)
mesoridazine (CHEBI:6780) is a phenothiazines (CHEBI:38093)
mesoridazine (CHEBI:6780) is a sulfoxide (CHEBI:22063)
mesoridazine (CHEBI:6780) is a tertiary amino compound (CHEBI:50996)
Incoming mesoridazine besylate (CHEBI:6781) has part mesoridazine (CHEBI:6780)
IUPAC Name
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfinyl)-10H-phenothiazine
INNs Sources
mesoridazina ChemIDplus
mesoridazine ChemIDplus
mesoridazinum ChemIDplus
Synonyms Sources
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine ChemIDplus
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazine ChemIDplus
2-Methanesulfinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazine ChEMBL
Mesoridazine KEGG COMPOUND
thioridazine thiomethyl sulfoxide ChemIDplus
thioridazine-2-sulfoxide ChemIDplus
TPS-23 ChEMBL
Database Links Databases
1712 DrugCentral
C07143 KEGG COMPOUND
D02671 KEGG DRUG
DB00933 DrugBank
LSM-1329 LINCS
Mesoridazine Wikipedia
US3084161 Patent
View more database links
Registry Numbers Types Sources
1033986 Reaxys Registry Number Reaxys
5588-33-0 CAS Registry Number ChemIDplus
5588-33-0 CAS Registry Number NIST Chemistry WebBook
Last Modified
22 February 2017
General Comment
2011-01-10 The use of mesoridazine, a phenothiazine antipsychotic with effects similar to chlorpromazine, is now restricted to the treatment of cases of schizophrenia in which other antipsychotics have produced an inadequate response. Its use in other psychiatric disorders was abandoned after results suggested an unacceptable balance of benefits and risks due to cardiotoxic potential. It is normally administered as the benzenesulfonic acid (besylate) salt.