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
Supplier Information ChemicalBook:CB31178981, ChemicalBook:CB9744071, eMolecules:975923
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Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use (especially with codeine). Promethazine is taken by mouth (oral), as a rectal suppository, or by injection into a muscle (IM). Common side effects of promethazine include confusion and sleepiness; consumption of alcohol or other sedatives can make these symptoms worse. It is unclear if use of promethazine during pregnancy or breastfeeding is safe for the fetus. Use of promethazine is not recommended in those less than two years old, due to potentially negative effects on breathing. Use of promethazine by injection into a vein is not recommended, due to potential skin damage. Promethazine is in the phenothiazine family of medications. It is also a strong anticholinergic, which produces its sedative effects. This also means high or toxic doses can act as a deliriant. Promethazine was made in the 1940s by a team of scientists from Rhône-Poulenc laboratories. It was approved for medical use in the United States in 1951. It is a generic medication and is available under many brand names globally. In 2022, it was the 198th most commonly prescribed medication in the United States, with more than 2 million prescriptions. In 2022, the combination with dextromethorphan was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
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Formula C21H26N2OS2
Net Charge 0
Average Mass 386.57400
Monoisotopic Mass 386.14866
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
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.
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
Manual Xrefs 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.