gepirone   Click here for help

GtoPdb Ligand ID: 12930

Synonyms: BMY-13805 | BMY13805 | Exxua® | MJ-13805 | MJ13805 | ORG-13011 | Travivo (gepirone extended-release)
Approved drug
gepirone is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Gepirone (BMY-13805) is a 5-HT1A receptor agonist [5].

gepirone is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 68.58
Molecular weight 359.47
XLogP 0.71
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1(C)CC(=O)N(CCCCN2CCN(CC2)C3=NC=CC=N3)C(=O)C1
Isomeric SMILES CC1(CC(=O)N(C(=O)C1)CCCCN2CCN(CC2)C3=NC=CC=N3)C
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
InChI Key QOIGKGMMAGJZNZ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Gepirone was evaluated as a treament for psychiatric conditions including major depressive disorder [4], generalised anxiety disorder and hypoactive sexual desire disorder [3] and drug dependency. The FDA approved gepirone as a treatment for major depressive disorder in September 2023. The trade name Exxua is an extended-release formulation that was previously known as Travivo.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00000189 Gepirone vs Placebo in Treatment of Cocaine Dependence - 3 Phase 2 Interventional University of Pennsylvania