CHEBI:6781 - mesoridazine besylate

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ChEBI Name mesoridazine besylate
ChEBI ID CHEBI:6781
Definition The benzenesulfonate salt of mesoridazine prepared using equimolar amounts of mesoridazine and benzenesulfonic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB31178981, ChemicalBook:CB9744071, eMolecules:975923
Download Molfile XML SDF
Formula C27H32N2O4S3
Net Charge 0
Average Mass 544.74900
Monoisotopic Mass 544.15242
InChI InChI=1S/C21H26N2OS2.C6H6O3S/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;7-10(8,9)6-4-2-1-3-5-6/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1-5H,(H,7,8,9)
InChIKey CRJHBCPQHRVYBS-UHFFFAOYSA-N
SMILES OS(=O)(=O)c1ccccc1.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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mesoridazine besylate (CHEBI:6781) has part mesoridazine (CHEBI:6780)
mesoridazine besylate (CHEBI:6781) has role dopaminergic antagonist (CHEBI:48561)
mesoridazine besylate (CHEBI:6781) has role first generation antipsychotic (CHEBI:65190)
mesoridazine besylate (CHEBI:6781) is a organosulfonate salt (CHEBI:64382)
IUPAC Name
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfinyl)-10H-phenothiazine benzenesulfonate
Synonyms Sources
(±)-10-(2-(1-methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine monobenzenesulfonate ChemIDplus
10-(2-(1-methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine monobenzenesulfonate ChemIDplus
mesoridazine benzenesulfonate ChemIDplus
mesoridazine monobenzenesulfonate ChEBI
NC 123 ChemIDplus
thioridazine-2-sulfoxide besylate ChEBI
Brand Names Sources
Lidanar ChEBI
Lidanil ChEBI
Serentil ChEBI
Serentil KEGG DRUG
Manual Xrefs Databases
D00795 KEGG DRUG
DB00933 DrugBank
View more database links
Registry Numbers Types Sources
32672-69-8 CAS Registry Number ChemIDplus
32672-69-8 CAS Registry Number KEGG DRUG
4121451 Reaxys Registry Number Reaxys
Last Modified
10 July 2012
General Comment
2011-01-10 Normally administered as the benzenesulfonic acid (besylate) salt, 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.