Gepirone

Gepirone
Clinical data
Trade names	Exxua
Other names	BMY-13805; MJ-13805; ORG-13011, Gepirone hydrochloride (USAN US)
Routes of; administration	Oral
ATC code	N06AX19 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	14–17%
Protein binding	72%
Metabolism	CYP3A4
Metabolites	3'-OH-gepirone; 1-(2-Pyrimidinyl)piperazine
Elimination half-life	IR: 2–3 hours; ER: 5 hours
Excretion	Urine: 81%; Feces: 13%
Identifiers
	IUPAC name 4,4-Dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione;
CAS Number	83928-76-1 ; 83928-66-9;
PubChem CID	55191;
DrugBank	DB12184; DBSALT002148;
ChemSpider	49836 ; 49835;
UNII	JW5Y7B8Z18; 80C9L8EP6V;
KEGG	D04314;
ChEBI	CHEBI:135990;
ChEMBL	ChEMBL284092 ; ChEMBL1204187;
CompTox Dashboard (EPA)	DTXSID90232813 ;
Chemical and physical data
Formula	C19H29N5O2
Molar mass	359.474 g·mol−1
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 ; Key:QOIGKGMMAGJZNZ-UHFFFAOYSA-N ;
	(verify)

Gepirone, sold under the brand name Exxua, is a medication used for the treatment of major depressive disorder.^[1] It is taken orally.^[1]

Side effects of gepirone include dizziness, nausea, insomnia, abdominal pain, and dyspepsia (indigestion).^[1] Gepirone acts as a partial agonist of the serotonin 5-HT_1A receptor.^[1]^[2] An active metabolite of gepirone, 1-(2-pyrimidinyl)piperazine, is an α₂-adrenergic receptor antagonist.^[1]^[3] Gepirone is a member of the azapirone group of compounds.^[2]

Gepirone was synthesized by Bristol-Myers Squibb in 1986 and was developed and marketed by Fabre-Kramer Pharmaceuticals.^[4] It was approved for the treatment of major depressive disorder in the United States in September 2023.^[4] This came after the drug had been rejected by the Food and Drug Administration three times over two decades due to insufficient evidence of effectiveness.^[5]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ "EXXUA (gepirone) extended-release tablets, for oral use" (PDF). Mission Pharmacal Company. U.S. Food and Drug Administration. 2023. Archived (PDF) from the original on 28 September 2023. Retrieved 28 September 2023.
^ ^a ^b Cite error: The named reference KishiMeltzer2013 was invoked but never defined (see the help page).
^ Cite error: The named reference HalbreichMontgomery2008 was invoked but never defined (see the help page).
^ ^a ^b "Gepirone - Fabre-Kramer Pharmaceuticals". AdisInsight. Springer Nature Switzerland AG. Archived from the original on 11 April 2023. Retrieved 28 September 2023.
^ Becker Z (28 September 2023). "Decades long regulatory odyssey ends with FDA nod for Fabre-Kramer's depression med Exxua". Fierce Pharma.

[Exxua-Label-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ "EXXUA (gepirone) extended-release tablets, for oral use" (PDF). Mission Pharmacal Company. U.S. Food and Drug Administration. 2023. Archived (PDF) from the original on 28 September 2023. Retrieved 28 September 2023.

[KishiMeltzer2013-2] Cite error: The named reference KishiMeltzer2013 was invoked but never defined (see the help page).

[HalbreichMontgomery2008-3] Cite error: The named reference HalbreichMontgomery2008 was invoked but never defined (see the help page).

[AdisInisght-4] "Gepirone - Fabre-Kramer Pharmaceuticals". AdisInsight. Springer Nature Switzerland AG. Archived from the original on 11 April 2023. Retrieved 28 September 2023.

[Becker2023-5] Becker Z (28 September 2023). "Decades long regulatory odyssey ends with FDA nod for Fabre-Kramer's depression med Exxua". Fierce Pharma.

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