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].
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 CDK toolkit. 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
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.

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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
References
1. Barbhaiya RH, Shukla UA, Pfeffer M, Pittman KA, Shrotriya R, Laroudie C, Gammans RE. (1994)
Disposition kinetics of buspirone in patients with renal or hepatic impairment after administration of single and multiple doses.
Eur J Clin Pharmacol, 46 (1): 41-7. [PMID:7911763]
2. Becker OM, Dhanoa DS, Marantz Y, Chen D, Shacham S, Cheruku S, Heifetz A, Mohanty P, Fichman M, Sharadendu A et al.. (2006)
An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression.
J Med Chem, 49 (11): 3116-35. [PMID:16722631]
3. Celada P, Bortolozzi A, Artigas F. (2013)
Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research.
CNS Drugs, 27 (9): 703-16. [PMID:23757185]
4. Feiger AD, Heiser JF, Shrivastava RK, Weiss KJ, Smith WT, Sitsen JM, Gibertini M. (2003)
Gepirone extended-release: new evidence for efficacy in the treatment of major depressive disorder.
J Clin Psychiatry, 64 (3): 243-9. [PMID:12716264]
5. Kaur Gill A, Bansal Y, Bhandari R, Kaur S, Kaur J, Singh R, Kuhad A, Kuhad A. (2019)
Gepirone hydrochloride: a novel antidepressant with 5-HT1A agonistic properties.
Drugs Today (Barc), 55 (7): 423-437. [PMID:31347611]
6. Timmer CJ, Sitsen JM. (2003)
Pharmacokinetic evaluation of gepirone immediate-release capsules and gepirone extended-release tablets in healthy volunteers.
J Pharm Sci, 92 (9): 1773-8. [PMID:12949996]