OCINAPLON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H11N5O
Molecular Weight	301.3021
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(C1=C2N=CC=C(N2N=C1)C3=CC=NC=C3)C4=NC=CC=C4

InChI

InChIKey=OQJFBUOFGHPMSR-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H11N5O
Molecular Weight	301.3021
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15870187
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800001407 https://en.wikipedia.org/wiki/Ocinaplon

Ocinaplon is anxiolytic in rodents and primates, including humans, with a magnitude of effect comparable to benzodiazepines. It was evaluated to treat Generalised anxiety disorder. The mechanism of action by which ocinaplon produces its anxiolytic effects is by allosteric modulating of GABA-A receptors. The serious adverse event detected in the ocinaplon group was icterus following transaminase elevations. Due to liver complications that occurred in Phase III, development of ocinaplon is discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21762686 https://www.ncbi.nlm.nih.gov/pubmed/15926867 https://www.ncbi.nlm.nih.gov/pubmed/15870187 https://www.ncbi.nlm.nih.gov/pubmed/18554397	Positive Allosteric Modulator 179		2.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Generalized anxiety disorder 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20041911	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AChemBlock	M23586	http://www.achemblock.com/catalogsearch/result/?q=M23586
AK Scientific	3778AL	https://aksci.com/item_detail.php?cat=3778AL
AbovChem LLC	AC160620	http://www.abovchem.com/pc/en/product_list.aspx?wd=AC160620
ApexBio Technology	B5582	https://www.apexbt.com/catalogsearch/result/?q=B5582
AstaTech	87647	http://astatechinc.com/CPSResult.php?CRNO=87647
BLD Pharm	BD149680	http://www.bldpharm.com/search/Search.html?keyword=BD149680
BOC Sciences	96604-21-6	http://www.bocsci.com/description.asp?cas=96604-21-6
ChemShuttle	172237	https://www.chemshuttle.com/catalogsearch/result/?q=172237
Hairui	HR148889	http://www.hairuichem.com/en/product/search.do?q=HR148889
KeyOrganics	AS-72567	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-72567
Lab Network	LN00333131	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00333131
MolPort	MolPort-023-277-179	https://www.molport.com/shop/molecule-link/MolPort-023-277-179
MuseChem	I010950	https://www.musechem.com/product/I010950.html
Princeton BioMolecular Research	PBMR221744	http://www.princetonbio.com/order_online?common_id=PBMR221744
Tetrahedron	TS74699	http://www.thsci.com/search.do?q=TS74699
Tocris	4410	https://www.tocris.com/search.php?Type=QuickSearch&Value=4410
eMolecules	36096428	https://orderbb.emolecules.com/search/#?query=36096428
eNovation Chemicals	D772618	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D772618&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-5215110788	https://mcule.com/MCULE-5215110788/

PubMed

Title	Date	PubMed
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003 Aug	12871032
The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics.	2005 May	15926867
Comparative cue generalization profiles of L-838, 417, SL651498, zolpidem, CL218,872, ocinaplon, bretazenil, zopiclone, and various benzodiazepines in chlordiazepoxide and zolpidem drug discrimination.	2006 Mar	16339395
Pharmacological Properties of DOV 315,090, an ocinaplon metabolite.	2008 Jun 13	18554397
GABA-A receptor modulators: can they offer any improvement over benzodiazepines in the treatment of anxiety disorders?	2010 Apr	20415836
A multicenter, placebo-controlled, double-blind, randomized study of efficacy and safety of ocinaplon (DOV 273,547) in generalized anxiety disorder.	2010 Apr	20041911

Patents

Sample Use Guides

In Vivo Use Guide

90 mg three times a day

Route of Administration: Oral

In Vitro Use Guide

Ocinaplon was ≈3-fold more potent in inhibiting [3H]flunitrazepam binding to rat cerebellum than cortex (IC50 values of 1.2 μM and 3.8 μM, respectively, with Hill coefficients 0.9 and 0.7 in cerebellum and cortex, respectively).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:20 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:20 GMT 2023`
Record UNII	2H6KVC5E76
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OCINAPLON

Official Name

English

METHANONE, 2-PYRIDINYL(7-(4-PYRIDINYL)PYRAZOLO(1,5-A)PYRIMIDIN-3-YL)-

Systematic Name

English

CL 273,547

Code

English

OCINAPLON [USAN]

Common Name

English

2-Pyridyl 7-(4-pyridyl)pyrazolo[1,5-a]pyrimidin-3-yl ketone

Systematic Name

English

ocinaplon [INN]

Common Name

English

CL-273547

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197