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    Estetrol

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    2D Structure
    Also known as: 15183-37-6, Estetrol anhydrous, 15.alpha.-hydroxyestriol, Enb39r14vf, (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, Estetrol (usan)
    Molecular Formula
    C18H24O4
    Molecular Weight
    304.4  g/mol
    InChI Key
    AJIPIJNNOJSSQC-NYLIRDPKSA-N
    FDA UNII
    ENB39R14VF
    A metabolite of ESTRIOL with a 15-alpha-hydroxyl group. Estetrol can be converted from estriol sulfate or DEHYDROEPIANDROSTERONE SULFATE by the fetal-placental unit.
    Estetrol anhydrous is an Estrogen. The mechanism of action of estetrol anhydrous is as an Estrogen Receptor Agonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 InChI
    InChI=1S/C18H24O4/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/t12-,13-,14-,15-,16-,17+,18+/m1/s1
    2.1.3 InChI Key
    AJIPIJNNOJSSQC-NYLIRDPKSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1C(C(C2O)O)O)CCC4=C3C=CC(=C4)O
    2.1.5 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
    2.2 Other Identifiers
    2.2.1 UNII
    ENB39R14VF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 15 Alpha Hydroxy Estriol

    2. 15 Alpha Hydroxyestriol

    3. 15 Alpha-hydroxyestriol

    4. 15-alpha-hydroxy-estriol

    2.3.2 Depositor-Supplied Synonyms

    1. 15183-37-6

    2. Estetrol Anhydrous

    3. 15.alpha.-hydroxyestriol

    4. Enb39r14vf

    5. (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

    6. Estetrol (usan)

    7. Estetrol [usan]

    8. (8r,9s,13s,14s,15r,16r,17r)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,15,16,17-tetraol

    9. E4

    10. (14beta,15alpha,16alpha,17alpha)-estra-1,3,5(10)-triene-3,15,16,17-tetrol

    11. E-4

    12. Unii-enb39r14vf

    13. Estell

    14. Estetrolum

    15. Oestetrol

    16. Donesta

    17. Estetrol (anhydrous)

    18. 15alpha-hydroxyestriol

    19. 15 Alpha-hydroxyestriol

    20. Estetrol [inn]

    21. Estetrol [who-dd]

    22. Mls006010253

    23. Schembl145580

    24. Estetrol, >=98% (hplc)

    25. Chembl1230314

    26. Gtpl11591

    27. Dtxsid50164888

    28. Chebi:142773

    29. Bdbm158505

    30. Zinc5764481

    31. Estetrol (anhydrous) [usan]

    32. Who 10439

    33. Akos030254521

    34. At27982

    35. Db12235

    36. Ncgc00345819-03

    37. Hy-15731

    38. Smr004701329

    39. Us9034854, E4

    40. Cs-0008552

    41. D11513

    42. J-008852

    43. Q5401078

    44. Drovelis (ema); ; Estetrol Monohydrate + Drospirenone

    45. Lydisilka (ema); ; Estetrol Monohydrate + Drospirenone

    46. Nextstellis (us); Estetrol Monohydrate + Drospirenone

    47. 1,3,5(10)-estratrien-3,15alpha,16alpha,17beta-tetrol

    48. Estra-1(10),2,4-triene-3,15alpha,16alpha,17beta-tetrol

    49. Estra-1,3,5(10)-triene-3,15alpha,16alpha,17beta-tetrol

    50. 3,15alpha,16alpha,17beta-tetrahydroxyestra-1,3,5(10)-triene

    51. Estra-1,3,5(10)-triene-3,15 Alpha,16alpha,17beta-tetrol

    52. (15alpha,16alpha,17beta)-estra-1(10),2,4-triene-3,15,16,17-tetrol

    53. Estra-1,3,5(10)-triene-3,15,16,17-tetrol, (15alpha,16alpha,17beta)-

    54. Estra-1,3,5(10)-triene-3,15.alpha.,16.alpha.,17.beta.-tetrol

    55. Estra-1,3,5(10)-triene-3,15,16,17-tetrol, (15.alpha.,16.alpha.,17.beta.)-

    56. 4oh

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 304.4 g/mol
    Molecular Formula C18H24O4
    XLogP31.5
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count0
    Exact Mass304.16745924 g/mol
    Monoisotopic Mass304.16745924 g/mol
    Topological Polar Surface Area80.9 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity441
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Estetrol is indicated in combination with drospirenone for the prevention of pregnancy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Estetrol prevents pregnancy by suppressing ovulation.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ESTETROL ANHYDROUS
    5.2.2 FDA UNII
    ENB39R14VF
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Estrogen Receptor Agonists
    5.3 Absorption, Distribution and Excretion

    Absorption

    Estetrol is rapidly absorbed from the gastrointestinal tract. The Cmax of estetrol is 18 ng/mL according to the results of a pharmacokinetic study, with an AUC of 36.4 ngh/mL. When estetrol and drospirenone are taken in a single product, maximum serum concentrations of approximately 48.7 ng/mL are achieved within 1-3 h. Bioavailability of the combination ranges between 76 and 85%. The Tmax can range from 0.5 to 2 hours and time to steady state is approximately 4 days, according to the results of one clinical study.

    Route of Elimination

    Estrogens are generally excreted as sulfated and glucuronidated derivatives. Approximately 69% of a dose of estetrol is excreted in the urine, and about 22% is excreted in the feces as unchanged drug.

    Volume of Distribution

    Limited distribution of estetrol into red blood cells has been demonstrated.

    5.4 Metabolism/Metabolites

    Estretol is heavily metabolized after oral administration. Phase 2 metabolism of estrogen forms glucuronide and sulfate conjugates with negligible in-vitro estrogenic activity. In vitro metabolism studies demonstrate that UGT2B7 catalyzes the formation of E4-16-glucuronide. Estetrol is combined with [drospirenone] in a product. The hepatic cytochrome enzyme CYP3A4 metabolizes drospirenone to two primary metabolites: the acid form of drospirenone through the opening of the lactone ring and the 4,5 dihydrodrospirenone formed by reduction, followed by sulfation. Both metabolites are pharmacologically inactive.

    5.5 Biological Half-Life

    The elimination half-life of estetrol is approximately 27 hours. Half-life may range between 19-40 hours.

    5.6 Mechanism of Action

    Estetrol is a synthetic analogue of a naturally occurring estrogen present during pregnancy, demonstrating selectivity for both estrogen receptor- (ER-) and ER- and suppressing ovulation. Estetrol binds with a low to moderate affinity human estrogen receptor alpha (ER alpha) and ER beta with a preference for ER alpha. Estetrol demonstrates a unique mechanism of action via tissue selective activity, showing estrogen receptor agonist activity on the vagina, the uterus and the endometrium, and negative estrogenic activity on breast tissue.