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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

Molecular Formula C16H23N7O2
Molecular Weight 345.3995
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPTAPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.5 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
Other AEs: Dizziness...
Other AEs:
Dizziness
Sources:
AEs

AEs

AESignificanceDosePopulation
Dizziness
1.5 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential.
1998 Oct
5-HT1A receptor activation and anti-cataleptic effects: high-efficacy agonists maximally inhibit haloperidol-induced catalepsy.
2002 Oct 25
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:36:10 UTC 2023
Edited
by admin
on Fri Dec 15 15:36:10 UTC 2023
Record UNII
3M824XRO8N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPTAPIRONE
INN   WHO-DD  
INN  
Official Name English
eptapirone [INN]
Common Name English
Eptapirone [WHO-DD]
Common Name English
4-METHYL-2-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-AS-TRIAZINE-3,5(2H,4H)-DIONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C65524
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
WIKIPEDIA
Eptapirone
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
INN
7801
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
CAS
179756-85-5
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID40170857
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
FDA UNII
3M824XRO8N
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
MESH
C115127
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
PUBCHEM
208928
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104230
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
EVMPD
SUB01923MIG
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
SMS_ID
100000087267
Created by admin on Fri Dec 15 15:36:10 UTC 2023 , Edited by admin on Fri Dec 15 15:36:10 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY