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Compound Detail

CHEMBL411

DIETHYLSTILBESTROL
💊 Approved Drug
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💊 Approved Drug
CC/C(=C(/CC)c1ccc(O)cc1)c1ccc(O)cc1

Basic Information

ChEMBL ID CHEMBL411
Name DIETHYLSTILBESTROL
Phase Approved
Structure Type MOL
InChI Key RGLYKWWBQGJZGM-ISLYRVAYSA-N
Therapeutic ✓ Yes

Known Names

Apstil Diethylstilbestrol Dietilestilbestrol Distilbene NSC-3070 Stilbestro Stilbestrol Stilbetin Stilboesterol Tampovagan
52
Targets
117
Activities
3
Assay Types
1
PK Parameters
20
Publications
10
Known Names
2
Indications
1
Mechanisms

Molecular Properties

268.4
MW (Da)
4.83
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.78
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem -estr-

Extended Properties

Molecular Formula C18H20O2
MW 268.36
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.24

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Estrogen receptor alpha agonist AGONIST Estrogen receptor

Indications

Neoplasms Prostatic Neoplasms, Castration-Resistant

ATC Classification

G03CB02
diethylstilbestrol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03CC05
diethylstilbestrol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
L02AA01
diethylstilbestrol
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 64 meas. best 9.48
Ki 42 meas. best 9.9
EC50 11 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor beta
CHEMBL242
EC50 10.7 9.375 0.0 2
Estrogen receptor
CHEMBL206
EC50 10.22 9.28 0.1 5
Estrogen receptor
CHEMBL2093866
Ki 9.9 9.895 0.1 2
Estrogen receptor
CHEMBL206
Ki 9.7 9.5625 0.2 4
Estrogen receptor
CHEMBL206
IC50 9.48 8.46 0.3 5
MCF7
CHEMBL387
IC50 9.4 7.35 0.4 2
Estrogen receptor beta
CHEMBL242
Ki 9.2 9.2 0.6 1
Estrogen receptor beta
CHEMBL242
IC50 8.4 7.305 4.0 2
Aldehyde oxidase
CHEMBL3257
IC50 6.34 6.34 460.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 6.3 6.3 500.0 1
Progesterone receptor
CHEMBL1909044
Ki 6.21 6.21 611.0 1
Estrogen-related receptor gamma
CHEMBL4245
EC50 6.2 6.2 630.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.07 6.07 851.0 1
Delta-type opioid receptor
CHEMBL236
Ki 6.02 6.02 958.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.97 5.97 1071.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.9 5.9 1248.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.86 5.86 1369.0 1
Adenosine receptor A1
CHEMBL226
Ki 5.78 5.78 1666.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.74 5.74 1825.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.7 5.7 1998.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.66 5.66 2201.0 1
Adenosine receptor A3
CHEMBL256
IC50 5.66 5.66 2208.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.63 5.63 2345.0 1
NIH3T3
CHEMBL614822
IC50 5.6 5.6 2500.0 1
Delta-type opioid receptor
CHEMBL236
IC50 5.57 5.57 2718.0 1
Trypanosoma brucei
CHEMBL612849
EC50 5.55 5.55 2800.0 1
Adenosine receptor A1
CHEMBL226
IC50 5.54 5.54 2856.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.53 5.53 2987.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
IC50 5.53 5.53 2963.0 1
ANN-1
CHEMBL614520
IC50 5.52 5.52 3000.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.5 5.5 3140.0 1
Substance-K receptor
CHEMBL2327
Ki 5.5 5.5 3184.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.44 5.44 3640.0 1
Unchecked
CHEMBL612545
Ki 5.44 5.0533 3650.0 6
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.44 5.44 3654.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.43 5.43 3670.0 1
Unchecked
CHEMBL612545
IC50 5.42 4.917 3761.0 10
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.41 5.41 3907.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 5.41 5.41 3882.0 1
Thromboxane-A synthase
CHEMBL1835
IC50 5.36 5.36 4359.0 1
D(2) dopamine receptor
CHEMBL217
Ki 5.35 5.35 4440.0 1
Kappa-type opioid receptor
CHEMBL237
IC50 5.34 5.34 4563.0 1
Progesterone receptor
CHEMBL1909044
IC50 5.33 5.33 4682.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.32 5.32 4790.0 1
Glucocorticoid receptor
CHEMBL2034
Ki 5.32 5.32 4818.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.3 5.3 5060.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.28 5.28 5297.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.27 5.27 5321.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.27 5.27 5340.0 1
Prostaglandin G/H synthase 1
CHEMBL221
IC50 5.25 5.25 5600.0 1

Pharmacokinetic Data

Parameter Value Units Species
KA 4e-10 M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor beta EC50 = 0.02 nM 10.7 Activation of estrogen response element in HeLa cells stably transfected with hu... 11906280
Estrogen receptor EC50 = 0.06 nM 10.22 Activation of estrogen response element in HeLa cells stably transfected with hu... 11906280
Estrogen receptor EC50 = 0.11 nM 9.96 Selective estrogen receptor down-regulator activity at FLAG-tagged ERalpha (unkn... 30940565
Estrogen receptor Ki = 0.126 nM 9.9 Inhibition of estradiol binding to estrogen receptor in Human Breast cancer cyto... 9216828
Estrogen receptor Ki = 0.128 nM 9.89 Apparent inhibition constant for estrogen receptor in Human uterine cytosol in 3... 9216828
Estrogen receptor EC50 = 0.2 nM 9.7 Agonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 cel... 30940565
Estrogen receptor Ki = 0.2 nM 9.7 Displacement of [3H]estradiol from human ER-alpha expressed in Sf21 cells incuba... 38401456
Estrogen receptor Ki = 0.22 nM 9.66 Displacement of [3H]Estradiol from human recombinant estrogen receptor alpha exp... 23403082
Estrogen receptor Ki = 0.261 nM 9.58 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor IC50 = 0.33 nM 9.48 Displacement of radioligand from Estrogen receptor alpha 11965371
MCF7 IC50 = 0.4 nM 9.4 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 33257172
Estrogen receptor Ki = 0.49 nM 9.31 In vitro displacement of 0.5 nM [3H]17-beta-estradiol from human Estrogen recept... 12672240
Estrogen receptor beta Ki = 0.63 nM 9.2 In vitro displacement of 0.5 nM [3H]17-beta-estradiol from human Estrogen recept... 12672240
Estrogen receptor IC50 = 0.7 nM 9.15 Displacement of [3H]estradiol from human ER-alpha expressed in Sf21 cells incuba... 38401456
Estrogen receptor IC50 = 0.915 nM 9.04 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor EC50 = 2.5 nM 8.6 Agonist activity at ER-alpha (unknown origin) by ER-alpha coactivator assay 38401456
Estrogen receptor IC50 = 3.0 nM 8.52 In vitro inhibition of [3H]17-beta-estradiol binding to human estrogen receptor ... 11356100
Estrogen receptor beta IC50 = 4.0 nM 8.4 In vitro inhibitory concentration against [3H]17-beta-estradiol binding to human... 11356100
Estrogen receptor beta EC50 = 9.0 nM 8.05 Inhibition of [3H]17-beta-estradiol binding to human recombinant Estrogen recept... 11906280
Estrogen receptor EC50 = 12.0 nM 7.92 Inhibition of [3H]17-beta-estradiol binding to human recombinant Estrogen recept... 11906280

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 593
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
26408814 10.1016/j.ejmech.2015.09.005 Nuclear receptor subfamily 1 group I member 2 6
30940565 10.1016/j.bmc.2019.03.042 Estrogen receptor 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 5
30613324 10.1021/acsmedchemlett.8b00324 ATP-dependent translocase ABCB1 4
9216828 10.1021/jm970095o Estrogen receptor 4
23403082 10.1016/j.bmcl.2013.01.025 Estrogen receptor 3
1255671 10.1021/jm00225a024 Mus musculus 3
19286283 10.1016/j.ejmech.2009.02.006 Estrogen receptor 3
19286283 10.1016/j.ejmech.2009.02.006 Estrogen receptor beta 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
12533678 - Broad substrate specificity ATP-binding cassette transporter ABCG2 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
1249803 10.1021/jm00224a006 Mus musculus 3
19286283 10.1016/j.ejmech.2009.02.006 Unchecked 3

Data from ChEMBL 36 via Core Engine