Ocinaplon

Ocinaplon

Clinical data
ATC code	none
Identifiers
IUPAC name pyridin-2-yl-(7-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-3-yl)methanone
CAS Number	96604-21-6 Y
PubChem CID	216456
IUPHAR/BPS	4277
ChemSpider	187602 Y
UNII	2H6KVC5E76
KEGG	D02617 Y
Chemical and physical data
Formula	C17H11N5O
Molar mass	301.302 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(c1cnn2c(ccnc12)c3ccncc3)c4ncccc4
InChI InChI=1S/C17H11N5O/c23-16(14-3-1-2-7-19-14)13-11-21-22-15(6-10-20-17(13)22)12-4-8-18-9-5-12/h1-11H Y Key:OQJFBUOFGHPMSR-UHFFFAOYSA-N Y

Ocinaplon is an anxiolytic drug in the pyrazolopyrimidine family of drugs. Other pyrazolopyrimidine drugs include zaleplon 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.

The mechanism of action by which ocinaplon produces its anxiolytic effects is by modulating GABA_A receptors, although ocinaplon is more subtype-selective than most benzodiazepines.

Development of ocinaplon is discontinued due to liver complications that occurred in one of the Phase III subjects.

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 in which the nitrile is replaced by a 2-acetylpyridil moiety. This affords the anxiolytic agent ocinaplon (5).