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Compound Detail

CHEMBL90593

PRASTERONE
💊 Approved Drug
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💊 Approved Drug
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL90593
Name PRASTERONE
Phase Approved
Structure Type MOL
InChI Key FMGSKLZLMKYGDP-USOAJAOKSA-N
Therapeutic ✓ Yes

Known Names

Androst-5-en-3.alpha.-ol-17-one Biolaif Dehydroandrosterone Dehydroepiandrosterone Dehydroisoandrosterone Dhea EM-760 Enzymatic therapy Intrarosa Isoandrostenolone Natrol dhea NSC-9896 +4 more
13
Targets
22
Activities
4
Assay Types
0
PK Parameters
20
Publications
16
Known Names
20
Indications
1
Mechanisms

Molecular Properties

288.4
MW (Da)
3.88
ALogP
2
HBA
1
HBD
37.3
PSA (Ų)
0.69
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Withdrawn Natural Product
USAN Stem -ster-; -terone
USAN Year 2015

Extended Properties

Molecular Formula C19H28O2
MW 288.43
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 2.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Arthritis, Rheumatoid Atrophic Vaginitis Atrophic Vaginitis Dysmenorrhea Osteoarthritis Pain Addison Disease Adrenal Insufficiency Aging Anorexia Nervosa Breast Neoplasms Genital Neoplasms, Female Infertility Lupus Erythematosus, Systemic Malaria Menopause Sexual Dysfunction, Physiological Skin Aging Crohn Disease Depressive Disorder

ATC Classification

A14AA07
prasterone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANABOLIC AGENTS FOR SYSTEMIC USE
G03XX01
prasterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Withdrawn
General Warning
lack of information on efficacy and safety of long-term use
Country: United States   Year: 1985

Activity Summary

IC50 15 meas. best 9.54
Ki 5 meas. best 5.96
EC50 1 meas. best 5.48
Kd 1 meas. best 7.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PC-12
CHEMBL612556
 IC50 9.54 9.54 0.3 1
Unchecked
CHEMBL612545
 IC50 8.78 6.69 1.6 2
Sex hormone-binding globulin
CHEMBL3305
 Kd 7.84 7.84 14.4 1
J774.A1
CHEMBL614040
 IC50 6.85 6.85 141.0 1
Glucose-6-phosphate 1-dehydrogenase
CHEMBL5672
 Ki 5.96 5.865 1100.0 2
T47D
CHEMBL614361
 IC50 5.59 5.59 2550.0 1
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 5.48 5.48 3330.0 1
Glucose-6-phosphate 1-dehydrogenase
CHEMBL5347
 Ki 5.21 5.13 6200.0 2
Corticosteroid-binding globulin
CHEMBL2421
 Ki 5.0 5.0 10000.0 1
Glucose-6-phosphate 1-dehydrogenase
CHEMBL5347
 IC50 4.95 4.85 11300.0 4
Trypanosoma cruzi
CHEMBL368
 IC50 4.86 4.535 13840.0 2
Jurkat
CHEMBL397
 IC50 4.33 4.33 46500.0 1
A549
CHEMBL392
 IC50 4.32 4.32 47800.0 2
Beta-glucuronidase
CHEMBL2728
 IC50 4.11 4.11 77900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PC-12 IC50 = 0.29 nM 9.54 Neuroprotective activity in rat PC12 cells assessed as inhibition of serum depri... 19845386
Unchecked IC50 = 1.65 nM 8.78 Displacement of [3H]DHEA from DHEA-binding site in rat PC12 cell membranes by ga... 19845386
Sex hormone-binding globulin Kd = 14.45 nM 7.84 Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding gl... 18330978
J774.A1 IC50 = 141.0 nM 6.85 Inhibition of LPS-induced TNFalpha production in mouse J774A.1 cells 17892941
Glucose-6-phosphate 1-dehydrogenase Ki = 1100.0 nM 5.96 Inhibition of Trypanosoma brucei G6PDH using NADP as substrate by Lineweaver-Bur... 19231202
Glucose-6-phosphate 1-dehydrogenase Ki = 1700.0 nM 5.77 Inhibition of Trypanosoma brucei G6PDH using glucose-6-phosphate as substrate by... 19231202
T47D IC50 = 2550.0 nM 5.59 Antiproliferative activity against human T47D cells assessed as reduction in cel... 26866967
G-protein coupled bile acid receptor 1 EC50 = 3330.0 nM 5.48 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
Glucose-6-phosphate 1-dehydrogenase Ki = 6200.0 nM 5.21 Inhibition of human G6PDH using NADP as substrate by Lineweaver-Burke plot 19231202
Glucose-6-phosphate 1-dehydrogenase Ki = 8900.0 nM 5.05 Inhibition of human G6PDH using glucose-6-phosphate as substrate by Lineweaver-B... 19231202
Corticosteroid-binding globulin Ki = 10000.0 nM 5.0 Binding affinity to human CBG receptor (corticosteroid-binding globulins) 15139751
Glucose-6-phosphate 1-dehydrogenase IC50 = 11300.0 nM 4.95 Inhibition of G6PD (unknown origin) 35239352
Glucose-6-phosphate 1-dehydrogenase IC50 = 11300.0 nM 4.95 Inhibition of human recombinant N-terminal His tagged G6PD expressed in Escheric... 22506561
Glucose-6-phosphate 1-dehydrogenase IC50 = 12460.0 nM 4.9 Inhibition of G6PD (unknown origin) assessed as reduction in 6-phospho-D-glucono... 33689874
Trypanosoma cruzi IC50 = 13840.0 nM 4.86 Trypanocidal activity against Trypanosoma cruzi ITRI/MX/2018/TH assessed as inhi... 34571489
Glucose-6-phosphate 1-dehydrogenase IC50 = 24900.0 nM 4.6 Inhibition of G6PD in HEK293T cells assessed as accumulation of 6-phosphoglucona... 22506561
Unchecked IC50 = 25000.0 nM 4.6 Inhibition of His-tagged Trypanosoma cruzi G6PDH expressed in Escherichia coli B... 20570159
Jurkat IC50 = 46500.0 nM 4.33 Antiproliferative activity against human Jurkat cells assessed as reduction in c... 26866967
A549 IC50 = 47800.0 nM 4.32 Cytotoxic activity against human A549 cells after 24 hrs by MTT assay 25456391
A549 IC50 = 47800.0 nM 4.32 Cytotoxic activity against human A549 cells after 48 hrs by MTT assay 25456391

Literature References

PubMed DOI Target Context # Activities
17350845 10.1016/j.bmc.2007.02.036 Unchecked 8
19231202 10.1016/j.bmc.2009.01.068 Glucose-6-phosphate 1-dehydrogenase 4
26866967 10.1016/j.ejmech.2016.01.058 T47D 4
22506561 10.1021/jm300317k Glucose-6-phosphate 1-dehydrogenase 3
20014752 10.1021/tx900326k Hepatotoxicity 3
26866967 10.1016/j.ejmech.2016.01.058 NON-PROTEIN TARGET 3
34571489 10.1016/j.bmc.2021.116417 Trypanosoma cruzi 3
19121874 10.1016/j.ejmech.2008.11.014 MDA-MB-468 2
19772289 10.1021/jm900921c 3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7 2
25456391 10.1016/j.bmc.2014.10.012 HeLa 2
25456391 10.1016/j.bmc.2014.10.012 A-431 2
18307294 10.1021/jm7015864 G-protein coupled bile acid receptor 1 2
25456391 10.1016/j.bmc.2014.10.012 A549 2
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B17 2
25456391 10.1016/j.bmc.2014.10.012 HT-29 2
25456391 10.1016/j.bmc.2014.10.012 LNCaP 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
25456391 10.1016/j.bmc.2014.10.012 MCF7 2
25456391 10.1016/j.bmc.2014.10.012 HepG2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine