Structure via PubChem · Public domain (PubChem)
estetrol
Sign in to saveAlso known as oestetrol, E4
Estetrol (E4), or oestetrol, is one of the four natural estrogenic steroid hormones found in humans, along with estrone (E1), estradiol (E2), and estriol (E3). Estetrol is a major estrogen in the body. In contrast to estrone and estradiol, estetrol is a native estrogen of fetal life. Estetrol is produced exclusively by the fetal liver and is found in detectable levels only during pregnancy, with relatively high levels in the fetus and lower levels in the maternal circulation.
Chemical data
- Formula
- C18H24O4
- Molecular weight
- 304.4 g/mol
- IUPAC name
- (8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O
- InChIKey
- AJIPIJNNOJSSQC-NYLIRDPKSA-N
- XLogP
- 1.5
- Polar surface area
- 80.9 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2021
- Admin. routes
- oral
- Indications
- contraception, vulvovaginitis, Hot flashes
via ChEMBL · EBI
Research
305 papersvia PubMed
Wikidata facts
- Mass
- 304.167
Show 4 more facts
- chemical formula
- C₁₈H₂₄O₄
- canonical SMILES
- CC12CCC3C(C1C(C(C2O)O)O)CCC4=C3C=CC(=C4)O
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O
- Commons category
- Estetrol
via Wikidata · CC0
~7 min read
Encyclopedic overview
15 sectionsContents
- Biological function
- Biological activity
- Mode of action
- Tissue-selective effect
- Differences vs SERMs
- ERα activation
- Biochemistry
- Biosynthesis
- Distribution
- Metabolism
- Excretion
- Chemistry
- Synthesis
- History
- References
Estetrol (E4), or oestetrol, is one of the four natural estrogenic steroid hormones found in humans, along with estrone (E1), estradiol (E2), and estriol (E3). Estetrol is a major estrogen in the body. In contrast to estrone and estradiol, estetrol is a native estrogen of fetal life. Estetrol is produced exclusively by the fetal liver and is found in detectable levels only during pregnancy, with relatively high levels in the fetus and lower levels in the maternal circulation.
In addition to its physiological role as a native hormone, estetrol can be used as a medication, see estetrol (medication). Estetrol, in combination with drospirenone, has recently been approved as a new estrogenic component of a combined oral contraceptive (COC) and estetrol alone is in clinical development for the treatment of menopausal symptoms as well as breast and prostate cancer.
Excerpted from Wikipedia’s “estetrol” article, available under the CC BY-SA 4.0 licence.