Compound: Gepirone
SMILES: O=C1N(C(=O)CC(C1)(C)C)CCCCN2CCN(c3ncccn3)CC2
InChIKey: QOIGKGMMAGJZNZ-UHFFFAOYSA-N
Synonyms: Gepirone, 83928-76-1, Gepirona, Gepironum, BMY-13805, MJ-13805, 4,4-dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione, Ariza, Org-33062 free base, JW5Y7B8Z18, BMY 13805, DTXSID90232813, MJ 13805, 2,6-Piperidinedione, 4,4-dimethyl-1-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-, 4,4-dimethyl-1-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-2,6-piperidinedione, 4,4-dimethyl-1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,6-piperidinedione, 4,4-Dimethyl-1-(4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl)-piperidine-2,6-dione, 4,4-dimethyl-1-(4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl)piperidine-2,6-dione, 4,4-Dimethyl-1-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-piperidine-2,6-dione, RefChem:142961, DTXCID20155304, N06AX19, 1-(4-(4-(4-(trifluoromethyl)-2-pyridinyl)-1-piperazinyl)butyl)-2-pyrrolidinone(E)-2-butenedioate, Org 13011, 4,4-Dimethyl-1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)piperidine-2,6-dione, Gepirone [INN], C19H29N5O2, MFCD00868196, CHEMBL284092, Variza, Gepironum [Latin], Gepirona [Spanish], 4,4-dimethyl-1-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}piperidine-2,6-dione, UNII-JW5Y7B8Z18, gepiron ER, 2,6-Piperidinedione, 4,4-dimethyl-1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-; 4,4-Dimethyl-1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,6-piperidinedione; Gepirone, Gepirone (Standard), A1ESA, GEPIRONE [WHO-DD], SCHEMBL79040, orb1306818, GTPL12930, CHEBI:135990, QOIGKGMMAGJZNZ-UHFFFAOYSA-N, BMY13805, Travivo (gepirone extended-release), BDBM50005132, AKOS015924526, DB12184, DS-4359, FO65115, HY-122422R, MJ13805, SB19632, EBC-2613075, NCGC00408912-01, AC-38202, DB-106225, HY-122422, CS-0085425, NS00068813, L001135, Q2650256, F9995-2711, 3,3-DIMETHYL-1-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)GLUTARIMIDE, 4,4-Dimethyl-1-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-piperidine-2,6-dione (Gepirone)
Theoretical properties:
molecular_formula: C19H29N5O2
molecular_weight: 359.5 g/mol
exact_mass: 359.23212518 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 6
heavy_atom_count: 26
topological_polar_surface_area: 69.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Gepirone is a member of the class of piperidones that is piperidine-2,6-dione substituted by a 4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl group at position 1 and two methyl groups at position 4. It has a role as an antidepressant, an anxiolytic drug and a serotonergic agonist. It is a member of pyrimidines, a N-alkylpiperazine and a member of piperidones. It is a conjugate base of a gepirone(1+).
chebi: A member of the class of piperidones that is piperidine-2,6-dione substituted by a 4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl group at position 1 and two methyl groups at position 4.
chembl: GEPIRONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Gepirone, sold under the brand name Exxua, is a medication used for the treatment of major depressive disorder. It is taken orally.
Side effects of gepirone include dizziness, nausea, insomnia, abdominal pain, and dyspepsia (indigestion). Gepirone acts as a partial agonist of the serotonin 5-HT1A receptor. An active metabolite of gepirone, 1-(2-pyrimidinyl)piperazine, is an α2-adrenergic receptor antagonist. Gepirone is a member of the azapirone group of compounds.
Gepirone was synthesized by Bristol-Myers Squibb in 1986 and was developed and marketed by Fabre-Kramer Pharmaceuticals. It was approved for the treatment of major depressive disorder in the United States in September 2023. 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.