Estetrol monohydrateProduct ingredient for Estetrol
- Name
- Estetrol monohydrate
- Drug Entry
- Estetrol
Naturally or synthetically produced steroid estrogens have a wide range of pharmaceutical uses ranging from hormonal contraception to the treatment of menopausal symptoms.15 Estetrol (E4) is a native estrogen occurring naturally during pregnancy, but can be synthesized from a plant source and used for contraception.14 It is more potent and is safer than the synthetic estrogen ethinylestradiol (EE2) found in 97% of oral contraceptive pills, reducing the environmental accumulation of unwanted endocrine disrupting chemicals (EDCs) that often lead to harmful epigenetic effects.15
On April 15 2021, Mayne Pharma Group Limited and Mithra Pharmaceuticals were granted FDA approval for the oral contraceptive Estelle/Nextstellis, a combination of drospirenone and estetrol. Estetrol is the first new estrogen introduced to the USA in over 50 years and is the first approved estetrol product in the world. The combination of drospirenone and estetrol offers a new choice with a favourable safety profile for women seeking contraceptive therapy.14 In Canada, Nextstellis was approved for use in March 2021; it was developed by Mithra and is marketed by Searchlight Pharma.18
- Accession Number
- DBSALT003173
- Structure
Structure for Estetrol monohydrate (DBSALT003173)
- Synonyms
- Estetrol (hydrate) / Estetrol monohydrate
- UNII
- KC3GI9UM9V
- CAS Number
- 2055649-81-3
- Weight
- Average: 322.401
Monoisotopic: 322.178023937 - Chemical Formula
- C18H26O5
- InChI Key
- XRJNAPXFAXBPAM-BVTDNVAGSA-N
- InChI
- InChI=1S/C18H24O4.H2O/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22;/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3;1H2/t12-,13-,14-,15-,16-,17+,18+;/m1./s1
- IUPAC Name
- (1R,2R,3R,3aS,3bR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,2,3,7-tetrol hydrate
- SMILES
- O.[H][C@@]12[C@@H](O)[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C=C3CC[C@@]21[H]
- External Links
- ChemSpider
- 81368162
- Wikipedia
- Estetrol_(medication)
- Predicted Properties
Property Value Source Water Solubility 1.38 mg/mL ALOGPS logP 1.37 ALOGPS logP 1.67 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 10.33 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 80.92 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 82.55 m3·mol-1 Chemaxon Polarizability 33.96 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon