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Ocinaplon is an
Condensation of 4-Acetylpyridine with N,N-Dimethylformamide dimethyl acetal ( DMFDMA) gives the "enamide" (3). This is then condensed with (3-Amino-1H-pyrazol-4-yl)(2-pyridinyl)methanone (4) (96219-90-8). This is the same intermediate as was used in the synthesis of
anxiolytic
An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiet ...
drug in the pyrazolopyrimidine family of drugs. Other pyrazolopyrimidine drugs include zaleplon
Zaleplon, sold under the brand names Sonata among others, is a sedative- hypnotic, used to treat insomnia. It is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class.
It is manufactured by King Pharmaceuticals and Gedeon Richte ...
and indiplon.
Ocinaplon has a similar pharmacological profile to the benzodiazepine family of drugs, but with mainly anxiolytic properties and relatively little sedative or amnestic effect.
Medical uses
A 2019 review found tentative evidence of benefit in anxiety.Mechanism of action
The mechanism of action by which ocinaplon produces its anxiolytic effects is by modulating GABAA receptors, although ocinaplon is more subtype-selective than most benzodiazepines.Availability
Development of ocinaplon is discontinued due to liver complications that occurred in one of the Phase III subjects.Synthesis
Condensation of 4-Acetylpyridine with N,N-Dimethylformamide dimethyl acetal ( DMFDMA) gives the "enamide" (3). This is then condensed with (3-Amino-1H-pyrazol-4-yl)(2-pyridinyl)methanone (4) (96219-90-8). This is the same intermediate as was used in the synthesis of zaleplon
Zaleplon, sold under the brand names Sonata among others, is a sedative- hypnotic, used to treat insomnia. It is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class.
It is manufactured by King Pharmaceuticals and Gedeon Richte ...
in which the nitrile is replaced by a 2-acetylpyridil moiety. This affords the anxiolytic
An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiet ...
agent ocinaplon (5).
References
{{GABAAR PAMs Hepatotoxins Pyrazolopyrimidines Sedatives Pyridines Ketones GABAA receptor positive allosteric modulators