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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 anxi ...
drug in the pyrazolopyrimidine
Pyrazolopyrimidines are a series of isomeric heterocyclic chemical compounds with the molecular formula C6H5N3. They form the central core of a variety of more complex chemical compounds including some pharmaceuticals and pesticides.
Pharmaceu ...
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
Indiplon (INN and USAN) is a nonbenzodiazepine, hypnotic sedative that was developed in two formulations—an immediate-release formulation for sleep onset, and a modified-release (also called controlled-release or extended-release) version fo ...
.
Ocinaplon has a similar pharmacological profile to the benzodiazepine
Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, ...
family of drugs, but with mainly anxiolytic properties and relatively little sedative
A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but t ...
or amnestic
Amnesia is a deficit in memory caused by brain damage or disease,Gazzaniga, M., Ivry, R., & Mangun, G. (2009) Cognitive Neuroscience: The biology of the mind. New York: W.W. Norton & Company. but it can also be caused temporarily by the use o ...
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 anxi ...
agent ocinaplon (5).
References
{{GABAAR PAMs Hepatotoxins Pyrazolopyrimidines Sedatives Pyridines Ketones GABAA receptor positive allosteric modulators