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Estetrol

Estetrol

Synopsis, Chemistry

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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

Estetrol

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 Formula	C₁₈H₂₄O₄
Molecular Weight	304.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Exact Mass	304.16745924 g/mol
Monoisotopic Mass	304.16745924 g/mol
Topological Polar Surface Area	80.9 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	441
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.