Ocinaplon

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Chemical compound

title: "Ocinaplon" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hepatotoxins", "pyrazolopyrimidines", "sedatives", "2-pyridyl-compounds", "ketones", "gabaa-receptor-positive-allosteric-modulators", "4-pyridyl-compounds"] description: "Chemical compound" topic_path: "general/hepatotoxins" source: "https://en.wikipedia.org/wiki/Ocinaplon" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 447927963 | IUPAC_name = pyridin-2-yl-(7-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-3-yl)methanone | image = Ocinaplon.svg | image_class = skin-invert-image | width = 150

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| IUPHAR_ligand = 4277 | CAS_number_Ref = | CAS_number = 96604-21-6 | ATC_prefix = none | ATC_suffix = | PubChem = 216456 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 187602 | UNII_Ref = | UNII = 2H6KVC5E76 | KEGG_Ref = | KEGG = D02617

| C=17 | H=11 | N=5 | O=1 | smiles = O=C(c1cnn2c(ccnc12)c3ccncc3)c4ncccc4 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = OQJFBUOFGHPMSR-UHFFFAOYSA-N 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.

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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/cd/Ocinaplon_synthesis.svg" caption="doi = 10.3762/bjoc.9.265 }}[http://www.arkat-usa.org/get-file/34069/ ARKIVOC 2010 (ii) 267-282]"] ::

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).

References

References

  1. (May 2005). "Selective anxiolysis produced by ocinaplon, a GABA(A) receptor modulator". Proceedings of the National Academy of Sciences of the United States of America.
  2. (February 2019). "Pharmacological treatments for generalised anxiety disorder: a systematic review and network meta-analysis". Lancet.
  3. (March 2006). "Comparative cue generalization profiles of L-838, 417, SL651498, zolpidem, CL218,872, ocinaplon, bretazenil, zopiclone, and various benzodiazepines in chlordiazepoxide and zolpidem drug discrimination". The Journal of Pharmacology and Experimental Therapeutics.
  4. (May 2005). "The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics". Expert Opinion on Investigational Drugs.
  5. (May 2005). "Selective anxiolysis produced by ocinaplon, a GABA(A) receptor modulator". Proceedings of the National Academy of Sciences of the United States of America.
  6. "DOV Pharmaceutical, Inc. Places Ocinaplon Phase III Clinical Trial On Hold". PR NewsWire.
  7. (October 2013). "An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles". Beilstein Journal of Organic Chemistry.
  8. [http://www.arkat-usa.org/get-file/34069/ ARKIVOC 2010 (ii) 267-282]
  9. (1986). "A-Amino Acetals: 2,2-Diethoxy-2-(4-Pyridyl)Ethylamine". Organic Syntheses.
  10. {{US patent. 4900836
  11. {{Cite patent

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hepatotoxinspyrazolopyrimidinessedatives2-pyridyl-compoundsketonesgabaa-receptor-positive-allosteric-modulators4-pyridyl-compounds