CHEBI:3619 - chlormezanone

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ChEBI Name chlormezanone
Definition A 1,3-thiazine that is 1,3-thiazinan-4-one S,S-dioxide in which a hydrogen at position 2 is substituted by a 4-chlorophenyl group and the hydrogen attached to the nitrogen is substituted by methyl. A non-benzodiazepine muscle relaxant, it was used in the management of anxiety and in the treatment of muscle spasms until being discontinued worldwide by its manufacturer in 1996, due to rare but serious cutaneous reactions.
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Formula C11H12ClNO3S
Net Charge 0
Average Mass 273.73600
Monoisotopic Mass 273.02264
InChI InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3
SMILES CN1C(c2ccc(Cl)cc2)S(=O)(=O)CCC1=O
Roles Classification
Application(s): antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
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.
muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
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ChEBI Ontology
Outgoing chlormezanone (CHEBI:3619) has role antipsychotic agent (CHEBI:35476)
chlormezanone (CHEBI:3619) has role anxiolytic drug (CHEBI:35474)
chlormezanone (CHEBI:3619) has role muscle relaxant (CHEBI:51371)
chlormezanone (CHEBI:3619) is a 1,3-thiazine (CHEBI:46975)
chlormezanone (CHEBI:3619) is a lactam (CHEBI:24995)
chlormezanone (CHEBI:3619) is a monochlorobenzenes (CHEBI:83403)
chlormezanone (CHEBI:3619) is a sulfone (CHEBI:35850)
Incoming (R)-chlormezanone (CHEBI:59467) is a chlormezanone (CHEBI:3619)
(S)-chlormezanone (CHEBI:59468) is a chlormezanone (CHEBI:3619)
2-(4-chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide
INNs Sources
chlormezanona ChemIDplus
chlormezanone ChemIDplus
chlormézanone WHO MedNet
chlormezanonum ChemIDplus
Synonyms Sources
(±)-chlormezanone ChemIDplus
2-(p-chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide ChemIDplus
2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide ChemIDplus
chlormethazanone ChemIDplus
Manual Xrefs Databases
603 DrugCentral
Chlormezanone Wikipedia
DB01178 DrugBank
GB815203 Patent
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Registry Numbers Types Sources
23033 Reaxys Registry Number Reaxys
23033 Beilstein Registry Number Beilstein
80-77-3 CAS Registry Number KEGG DRUG
80-77-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10191862 PubMed citation Europe PMC
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Last Modified
20 June 2018