Gepirone

Gepirone

Clinical data
Routes of administration	Oral
ATC code	N06AX19 (WHO)
Legal status
Legal status	In general: uncontrolled
Pharmacokinetic data
Elimination half-life	2-3 hours
Identifiers
IUPAC name 4,4-dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione
CAS Number	83928-76-1
PubChem CID	55191
ChemSpider	49836 Y
UNII	JW5Y7B8Z18
ChEMBL	ChEMBL284092 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H29N5O2
Molar mass	359.46586 g/mol
3D model (JSmol)	Interactive image
SMILES O=C1N(C(=O)CC(C)(C)C1)CCCCN3CCN(c2ncccn2)CC3
InChI InChI=1S/C19H29N5O2/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18/h5-7H,3-4,8-15H2,1-2H3 Y Key:QOIGKGMMAGJZNZ-UHFFFAOYSA-N Y
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Gepirone (Ariza, Variza; BMY-13,805, ORG-13,011) is an antidepressant and anxiolytic of the azapirone class. Like other azapirones, it acts as a selective partial agonist of the 5-HT_1A receptor. Gepirone was under development in the U.S. in an extended release form, but despite completing phase III clinical trials, it failed to pass the drug approval process. As a result, gepirone, despite already having brand names picked out, did not manage to reach the pharmaceutical market.

Gepirone was originally developed by Bristol-Myers Squibb, but was out-licensed to Fabre-Kramer in 1993. The U.S. Food and Drug Administration (FDA) rejected approval for gepirone in 2004. It was submitted for the preregistration (NDA) phase again in May 2007 after adding additional information from clinical trials as the FDA required in 2004. However, in 2007 it once again failed to convince the FDA of its qualities for treating anxiety and depression. There have been no updates on gepirone since.

Synthesis

[[ File:Gepirone synth.png|800px]]

Ormaza, V. A.; 1986, ES 8606333 .