Gepirone

Gepirone
Clinical data
Trade namesExxua
Other namesBMY-13805; MJ-13805; ORG-13011, Gepirone hydrochloride (USAN US)
Routes of
administration		By mouth[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability14–17%[1]
Protein binding72%[1]
MetabolismCYP3A4[1]
Metabolites3'-OH-gepirone; 1-(2-Pyrimidinyl)piperazine[1]
Elimination half-lifeIR: 2–3 hours
ER: 5 hours[1]
ExcretionUrine: 81%[1]
Feces: 13%[1]
Identifiers
  • 4,4-Dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H29N5O2
Molar mass359.474 g·mol−1
3D model (JSmol)
  • O=C1N(C(=O)CC(C)(C)C1)CCCCN3CCN(c2ncccn2)CC3
  • 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 checkY
  • Key:QOIGKGMMAGJZNZ-UHFFFAOYSA-N checkY
  (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-HT1A 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 (FDA) three times over two decades due to insufficient evidence of effectiveness.[5]

  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.
  2. ^ a b Cite error: The named reference KishiMeltzer2013 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference HalbreichMontgomery2008 was invoked but never defined (see the help page).
  4. ^ a b "Gepirone - Fabre-Kramer Pharmaceuticals". AdisInsight. Springer Nature Switzerland AG. Archived from the original on 11 April 2023. Retrieved 28 September 2023.
  5. ^ Becker Z (28 September 2023). "Decades long regulatory odyssey ends with FDA nod for Fabre-Kramer's depression med Exxua". Fierce Pharma.