Gepirone HydrochlorideProduct ingredient for Gepirone

Name
Gepirone Hydrochloride
Drug Entry
Gepirone

Gepirone, an azapirone, is a pharmacologic analog of buspirone that acts selectively on the pre- and post-synaptic 5HT1A receptors. Although earlier clinical trials showed promising results for gepirone, its formulation as an immediate-release tablet necessitates frequent administration due to the short half-lives. It was not until an extended-release formulation of gepirone was made available that gepirone became a potential candidate for a new antidepressant.1,2,3

Gepirone was approved by the FDA on September 28, 2023, under the brand name EXXUA for the treatment of adults with major depressive disorder. It represents a novel class of antidepressants that selectively targets the 5HT1A receptors, thus possessing a more favorable side effects profile with comparable incidence of sexual dysfunction side effects as that of the placebo.6

Accession Number
DBSALT002148
Structure
Synonyms
Not Available
UNII
80C9L8EP6V
CAS Number
83928-66-9
Weight
Average: 395.93
Monoisotopic: 395.2088029
Chemical Formula
C19H30ClN5O2
InChI Key
DGOCVISYYYQFEP-UHFFFAOYSA-N
InChI
InChI=1S/C19H29N5O2.ClH/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;1H
IUPAC Name
4,4-dimethyl-1-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}piperidine-2,6-dione hydrochloride
SMILES
Cl.CC1(C)CC(=O)N(CCCCN2CCN(CC2)C2=NC=CC=N2)C(=O)C1
ChemSpider
49835
ChEMBL
CHEMBL1204187
PharmGKB
PA166123367
Predicted Properties
PropertyValueSource
Water Solubility1.09 mg/mLALOGPS
logP2.09ALOGPS
logP1.35Chemaxon
logS-2.5ALOGPS
pKa (Strongest Basic)7.62Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area69.64 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity101.49 m3·mol-1Chemaxon
Polarizability40.92 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon