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Details

Stereochemistry ACHIRAL
Molecular Formula C16H23N7O2
Molecular Weight 345.3995
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPTAPIRONE

SMILES

CN1C(=O)C=NN(CCCCN2CCN(CC2)C3=NC=CC=N3)C1=O

InChI

InChIKey=NMYAHEULKSYAPP-UHFFFAOYSA-N
InChI=1S/C16H23N7O2/c1-20-14(24)13-19-23(16(20)25)8-3-2-7-21-9-11-22(12-10-21)15-17-5-4-6-18-15/h4-6,13H,2-3,7-12H2,1H3

HIDE SMILES / InChI

Description

Eptapirone is a potent, selective and efficacious 5-HT1A receptor agonist. In rats, it is readily bioavailable after oral administration. Likely, because of its high efficacy at 5-HT1A receptors, Eptapirone exerted powerful antidepressant- and anxiolytic-like activity in animal models. Eptapirone given in the evening suppresses REM (rapid eye movement) sleep more than buspirone and implies a greater central effect on serotonin receptors, which is consistent with the preclinical data that indicate it has greater efficacy than buspirone. It has little effect on other sleep stages. Eptapirone has been in phase I clinical trials for the treatment of anxiety and major depressive disorder. However, this research has been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.33 null [pKi]
5.75 null [pKi]
6.16 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
1.5 mg single, oral
EPTAPIRONE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
1.5 mg given in the evening
Route of Administration: Oral
In Vitro Use Guide
In cells transfected with human 5-HT1A receptors, Eptapirone inhibited forskolin-induced stimulation of cAMP with a pEC50 value of 6.80.