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Compound Detail

CHEMBL1201151

MESTRANOL
💊 Approved Drug
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💊 Approved Drug
C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@@]21C

Basic Information

ChEMBL ID CHEMBL1201151
Name MESTRANOL
Phase Approved
Structure Type MOL
InChI Key IMSSROKUHAOUJS-MJCUULBUSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL691

Known Names

33355 EE-3ME EE3 ME EE3-ME EE3ME EEI3ME Mestranol Mestranol component of enovid Mestranol component of norinyl Mestranol component of ovulen NSC-84032
8
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
11
Known Names
1
Mechanisms

Molecular Properties

310.4
MW (Da)
3.92
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.80
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Stem -estr-
USAN Year 1962

Extended Properties

Molecular Formula C21H26O2
MW 310.44
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.19

Mechanism of Action

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

Activity Summary

IC50 9 meas. best 7.75
Ki 7 meas. best 8.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
Ki 8.28 8.28 5.2 1
Estrogen receptor
CHEMBL206
IC50 7.75 7.75 18.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 7.66 7.66 22.0 1
MCF7
CHEMBL387
IC50 7.4 7.4 40.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 7.39 7.39 41.0 1
Unchecked
CHEMBL612545
IC50 6.7 5.975 200.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.86 5.86 1382.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.86 5.86 1371.0 1
Unchecked
CHEMBL612545
Ki 5.3 5.3 5021.0 1
Androgen receptor
CHEMBL3072
Ki 5.15 5.15 7121.0 1
Androgen receptor
CHEMBL3072
IC50 4.97 4.97 10682.0 1
Progesterone receptor
CHEMBL1909044
Ki 4.96 4.96 11010.0 1
Cannabinoid receptor 1
CHEMBL218
Ki 4.65 4.65 22532.0 1
Cannabinoid receptor 1
CHEMBL218
IC50 4.54 4.54 28540.0 1
Progesterone receptor
CHEMBL1909044
IC50 4.07 4.07 84414.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor Ki = 5.223 nM 8.28 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor IC50 = 18.0 nM 7.75 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Sodium-dependent serotonin transporter Ki = 22.0 nM 7.66 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
MCF7 IC50 = 40.0 nM 7.4 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 33257172
Sodium-dependent serotonin transporter IC50 = 41.0 nM 7.39 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Unchecked IC50 = 200.0 nM 6.7 Displacement of 17beta-[3H]estradiol from rabbit uterine estrogen receptor after... 536998
Sodium-dependent noradrenaline transporter IC50 = 1382.0 nM 5.86 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 1371.0 nM 5.86 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Unchecked Ki = 5021.0 nM 5.3 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Unchecked IC50 = 5601.0 nM 5.25 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Androgen receptor Ki = 7121.0 nM 5.15 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 10682.0 nM 4.97 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Progesterone receptor Ki = 11010.0 nM 4.96 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Cannabinoid receptor 1 Ki = 22532.0 nM 4.65 DRUGMATRIX: Cannabinoid CB1 radioligand binding (ligand: [3H] SR141716A) -
Cannabinoid receptor 1 IC50 = 28540.0 nM 4.54 DRUGMATRIX: Cannabinoid CB1 radioligand binding (ligand: [3H] SR141716A) -
Progesterone receptor IC50 = 84414.0 nM 4.07 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
16472241 10.2174/1570163043334794 Hepatotoxicity 18
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
536998 10.1021/jm00198a021 Unchecked 2
536998 10.1021/jm00198a021 Rattus norvegicus 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
3346872 10.1021/jm00398a014 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
22931300 10.1021/tx300075j Cytochrome P450 2D6 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine