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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2023)
IUPAC Name Click here for help
4,4-dimethyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]piperidine-2,6-dione
International Nonproprietary Names Click here for help
INN number INN
5676 gepirone
Synonyms Click here for help
BMY-13805 | BMY13805 | Exxua® | MJ-13805 | MJ13805 | ORG-13011 | Travivo (gepirone extended-release)
Database Links Click here for help
BindingDB Ligand 50005132
ChEBI CHEBI:135990
ChEMBL Ligand CHEMBL284092
DrugBank Ligand DB12184
GtoPdb PubChem SID 485206051
PubChem CID 55191
Search Google for chemical match using the InChIKey QOIGKGMMAGJZNZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QOIGKGMMAGJZNZ
Search PubMed clinical trials gepirone
Search PubMed titles gepirone
Search PubMed titles/abstracts gepirone
UniChem Compound Search for chemical match using the InChIKey QOIGKGMMAGJZNZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QOIGKGMMAGJZNZ-UHFFFAOYSA-N

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MedChemExpress
Gepirone (links to external site)
Cat. No. HY-122422