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Compound Detail

CHEMBL284092

GEPIRONE
💊 Approved Drug
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💊 Approved Drug
CC1(C)CC(=O)N(CCCCN2CCN(c3ncccn3)CC2)C(=O)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL284092
Name GEPIRONE
Phase Approved
Structure Type MOL
InChI Key QOIGKGMMAGJZNZ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ariza BMY-13805 Gepirona Gepirone Mj-13805 ORG-13011 ORG-33062 FREE BASE Variza
5
Targets
11
Activities
4
Assay Types
2
PK Parameters
20
Publications
8
Known Names
2
Indications
1
Mechanisms

Molecular Properties

359.5
MW (Da)
1.55
ALogP
6
HBA
0
HBD
69.6
PSA (Ų)
0.57
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2023
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1985

Extended Properties

Molecular Formula C19H29N5O2
MW 359.47
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness -1.31

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 1a (5-HT1a) receptor agonist AGONIST 5-hydroxytryptamine receptor 1A ✓ ✓

Indications

Cocaine-Related Disorders Depressive Disorder

ATC Classification

N06AX19
gepirone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 8 meas. best 7.89
EC50 1 meas. best 6.54
IC50 1 meas. best 6.94
Kd 1 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.89 7.695 13.0 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 7.5 7.33 31.8 2
D(2) dopamine receptor
CHEMBL217
 Ki 7.24 6.305 58.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Kd 7.1 7.1 79.4 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 IC50 6.94 6.94 114.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 6.54 6.54 288.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 5.62 5.62 2400.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.44 5.44 3630.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.505 hr Homo sapiens
T1/2 6.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 13.0 nM 7.89 Displacement of [3H]8-OH-DPAT from human 5HT1A receptor in HEK293 cells 16722631
5-hydroxytryptamine receptor 1A Ki = 31.8 nM 7.5 In vitro ability to displace [3H]8-hydroxy-2-(di-n-propylamino) tetralin binding... 1535661
5-hydroxytryptamine receptor 1A Ki = 31.8 nM 7.5 Binding affinity to 5-HT1A (unknown origin) 28850227
D(2) dopamine receptor Ki = 58.0 nM 7.24 Binding affinity to D2 receptor by radioligand binding assay 16722631
5-hydroxytryptamine receptor 1A Ki = 70.0 nM 7.16 Evaluated for binding affinity towards 5-hydroxytryptamine 1A receptor in rat br... 3172131
5-hydroxytryptamine receptor 1A Kd = 79.43 nM 7.1 Binding affinity to 5HT1A receptor 19754201
5-hydroxytryptamine receptor 1A IC50 = 114.0 nM 6.94 In vitro binding affinity against 5-hydroxytryptamine 1A receptor using [3H]8-OH... 15026055
5-hydroxytryptamine receptor 1A EC50 = 288.0 nM 6.54 Activity against 5HT1A receptor by Gi-[35S]GTP-gamma-S binding assay 16722631
Adrenergic receptor alpha-1 Ki = 2400.0 nM 5.62 Displacement of [3H]prazosin from adrenergic alpha-1 receptor in rat cerebral co... 16722631
5-hydroxytryptamine receptor 2A Ki = 3630.0 nM 5.44 Binding affinity to 5-HT2A (unknown origin) 28850227
D(2) dopamine receptor Ki = 4320.0 nM 5.37 Displacement of [3H]methylspiperone from human D2 receptor expressed in HEK cell... 28850227

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20014752 10.1021/tx900326k Hepatotoxicity 3
16722631 10.1021/jm0508641 5-hydroxytryptamine receptor 1A 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
1535661 10.1021/jm00091a004 5-hydroxytryptamine receptor 1A 2
6131130 10.1021/jm00356a014 Dopamine receptor 2
6131130 10.1021/jm00356a014 Rattus norvegicus 2
3172131 10.1021/jm00118a018 5-hydroxytryptamine receptor 1A 2
16722631 10.1021/jm0508641 Adrenergic receptor alpha-1 1
28850227 10.1021/acs.jmedchem.7b00315 5-hydroxytryptamine receptor 2A 1
19754201 10.1021/jm901096y 5-hydroxytryptamine receptor 1A 1
16722631 10.1021/jm0508641 Homo sapiens 1
16722631 10.1021/jm0508641 Dopamine D2 receptor and serotonin 1a receptor 1
16722631 10.1021/jm0508641 D(2) dopamine receptor 1
16722631 10.1021/jm0508641 Unchecked 1
6131130 10.1021/jm00356a014 Adrenergic receptor alpha-1 1
1535661 10.1021/jm00091a004 ADMET 1
1535661 10.1021/jm00091a004 No relevant target 1
15026055 10.1016/j.bmcl.2004.01.045 ADMET 1

Data from ChEMBL 36 via Core Engine