Mestranol

Summary

Mestranol (CHEMBL1201151) is an approved small-molecule prodrug.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Chemistry: 310.4 Da · C21H26O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1201151
Name	Mestranol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	6291
ChEBI	CHEBI:6784
Molecular formula	C21H26O2
Molecular weight	310.4
InChIKey	IMSSROKUHAOUJS-MJCUULBUSA-N

SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC

IUPAC name: (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

ChEBI definition: A terminal acetylenic compound that is (17α)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.

Pharmacological roles (ChEBI): prodrug, xenoestrogen.

Also known as: EE-3ME, EE3 ME, EE3ME, EEI3ME, Mestranol, Mestranol component of enovid, Mestranol component of norinyl, Mestranol component of ovulen, NSC-84032, SID8139980, MESTRANOL, SID29215140

Patent coverage: 3,043 distinct patent families (10,339 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 10,338 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: Nuclear receptor ROR-gamma, Prelamin-A/C, Glucocorticoid receptor, Estrogen receptor, Progesterone receptor, Cannabinoid receptor 1, Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Sodium-dependent dopamine transporter, Androgen receptor.

Bioactivity

ChEMBL activities: 14 potent at pChembl ≥ 5 of 19 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ESR1	8.28	Ki	5.22	nM	CHEMBL_ACT_7751583
ESR1	7.75	IC50	18	nM	CHEMBL_ACT_7751582
SLC6A4	7.66	Ki	22	nM	CHEMBL_ACT_7753739
SLC6A4	7.39	IC50	41	nM	CHEMBL_ACT_7753738
PGR	7.02	AC50	96	nM	CHEMBL_ACT_25222844
ESR1	6.87	AC50	136	nM	CHEMBL_ACT_25167100
P15207	6.67	AC50	215	nM	CHEMBL_ACT_25187309
NR3C1	6.29	AC50	516	nM	CHEMBL_ACT_25175622
SLC6A4	6	AC50	1000	nM	CHEMBL_ACT_25150085
LMNA	5.9	Potency	1259	nM	CHEMBL_ACT_3666462
SLC6A2	5.86	IC50	1382	nM	CHEMBL_ACT_7751514
SLC6A2	5.86	Ki	1371	nM	CHEMBL_ACT_7751515
P51450	5.15	Potency	7080	nM	CHEMBL_ACT_4979506
P15207	5.15	Ki	7121	nM	CHEMBL_ACT_7755783

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).