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Compound Detail

CHEMBL1200623

ETHYLESTRENOL
💊 Approved Drug
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💊 Approved Drug
CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21C

Basic Information

ChEMBL ID CHEMBL1200623
Name ETHYLESTRENOL
Phase Approved
Structure Type MOL
InChI Key AOXRBFRFYPMWLR-XGXHKTLJSA-N
Therapeutic ✓ Yes

Known Names

Durabolin-o Duraboral Ethylestrenol Ethylnandrol Ethyloestrenol Etilestrenol Maxibolin NSC-37726 Orabolin
9
Targets
15
Activities
2
Assay Types
0
PK Parameters
10
Publications
9
Known Names
1
Mechanisms

Molecular Properties

288.5
MW (Da)
5.09
ALogP
1
HBA
1
HBD
20.2
PSA (Ų)
0.67
QED
1
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -estr-
USAN Year 1962

Extended Properties

Molecular Formula C20H32O
MW 288.48
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 2.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Androgen Receptor agonist AGONIST Androgen receptor

ATC Classification

A14AB02
ethylestrenol
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANABOLIC AGENTS FOR SYSTEMIC USE

Activity Summary

IC50 9 meas. best 7.57
Ki 6 meas. best 7.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Androgen receptor
CHEMBL3072
Ki 7.75 7.75 18.0 1
Progesterone receptor
CHEMBL1909044
Ki 7.58 7.58 26.0 1
Androgen receptor
CHEMBL3072
IC50 7.57 7.57 27.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 7.37 7.37 43.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 7.09 7.09 81.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.98 6.98 104.0 1
Progesterone receptor
CHEMBL1909044
IC50 6.7 6.7 201.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 6.54 6.54 292.0 1
Estrogen receptor
CHEMBL206
Ki 6.5 6.5 320.0 1
Estrogen receptor
CHEMBL206
IC50 5.95 5.95 1121.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.89 5.89 1290.7 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.68 5.68 2098.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.68 5.68 2080.0 1
Unchecked
CHEMBL612545
IC50 5.2 5.2 6245.1 1
Acetylcholinesterase
CHEMBL220
IC50 5.19 5.19 6504.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Androgen receptor Ki = 18.0 nM 7.75 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Progesterone receptor Ki = 26.0 nM 7.58 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Androgen receptor IC50 = 27.0 nM 7.57 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Sodium-dependent serotonin transporter Ki = 43.0 nM 7.37 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 81.0 nM 7.09 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Muscarinic acetylcholine receptor M2 Ki = 104.0 nM 6.98 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Progesterone receptor IC50 = 201.0 nM 6.7 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Muscarinic acetylcholine receptor M2 IC50 = 292.0 nM 6.54 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Estrogen receptor Ki = 320.0 nM 6.5 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor IC50 = 1121.0 nM 5.95 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Cytochrome P450 2C19 IC50 = 1290.7 nM 5.89 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Sodium-dependent noradrenaline transporter IC50 = 2098.0 nM 5.68 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 2080.0 nM 5.68 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Unchecked IC50 = 6245.1 nM 5.2 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Acetylcholinesterase IC50 = 6504.0 nM 5.19 DRUGMATRIX: Acetylcholinesterase enzyme inhibition (substrate: acetylthiocholine... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 174
20020916 10.1080/15376510701857262 Phospholipidosis 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine