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Chemistry

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Also known as: 474-86-2, 7-dehydroestrone, Dihydroequilenin, 3-hydroxyestra-1,3,5(10),7-tetraen-17-one, Estra-1,3,5(10),7-tetraen-17-one, 3-hydroxy-, 1,3,5,7-estratetraen-3-ol-17-one

Molecular Formula

C₁₈H₂₀O₂

Molecular Weight

268.3 g/mol

InChI Key

WKRLQDKEXYKHJB-HFTRVMKXSA-N

FDA UNII

08O86EX0J4

An estrogenic steroid produced by HORSES. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the URINE of pregnant mares.

1 2D Structure

Equilin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(9S,13S,14S)-3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

2.1.2 InChI

InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1

2.1.3 InChI Key

WKRLQDKEXYKHJB-HFTRVMKXSA-N

2.1.4 Canonical SMILES

CC12CCC3C(=CCC4=C3C=CC(=C4)O)C1CCC2=O

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3C(=CCC4=C3C=CC(=C4)O)[C@@H]1CCC2=O

2.2 Other Identifiers

2.2.1 UNII

08O86EX0J4

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 474-86-2

2. 7-dehydroestrone

3. Dihydroequilenin

4. 3-hydroxyestra-1,3,5(10),7-tetraen-17-one

5. Estra-1,3,5(10),7-tetraen-17-one, 3-hydroxy-

6. 1,3,5,7-estratetraen-3-ol-17-one

7. Equilin [usp]

8. (9s,13s,14s)-3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-one

9. Nsc-10971

10. Mls000028624

11. Chebi:42309

12. 08o86ex0j4

13. Equilin (usp)

14. Smr000058656

15. 3-hydroxy-estra-1,3,5(10),7tetraen-17-one

16. Unii-08o86ex0j4

17. Ccris 9074

18. 3-hydroxyoestra-1,3,5(10),7-tetraen-17-one

19. Cas-474-86-2

20. Prestwick_219

21. Einecs 207-488-6

22. Nsc 10971

23. Brn 2624302

24. Opera_id_780

25. Equilin [mi]

26. Equilin [mart.]

27. Prestwick0_000850

28. Prestwick1_000850

29. Prestwick2_000850

30. Prestwick3_000850

31. Equilin [usp-rs]

32. Equilin [who-dd]

33. Dsstox_cid_27433

34. Dsstox_rid_82343

35. Dsstox_gsid_47433

36. Bspbio_000839

37. 4-08-00-01366 (beilstein Handbook Reference)

38. Mls001148117

39. Schembl124758

40. Spbio_002760

41. Bpbio1_000923

42. Chembl323533

43. Equilin [usp Monograph]

44. Dtxsid7047433

45. Hms1570j21

46. Hms2097j21

47. Hms2233a16

48. Hms3714j21

49. Hy-b1176

50. Nsc10971

51. Tox21_302641

52. 1,5,7-estratetraen-3-ol-17-one

53. Bdbm50423544

54. Lmst02010026

55. Akos024285096

56. Zinc100031739

57. Ccg-220850

58. Cs-4786

59. Db02187

60. Ncgc00179406-01

61. Ncgc00256728-01

62. Equilin, Vetranal(tm), Analytical Standard

63. 3-hydroxyestra-1,5(10),7-tetraen-17-one

64. Wln: L E5 B666 Fv Juttt&j E1 Oq

65. D04041

66. S00287

67. 3-hydroxy-estra-1,3,5(10), 7-tetraen-17-one

68. 3-hydroxy-estra-1,3,5(10),7-tetraen-17-one

69. Estra-1,5(10),7-tetraen-17-one, 3-hydroxy-

70. Sr-01000721841

71. Q5384492

72. Sr-01000721841-2

73. Brd-k04046242-001-03-6

74. Equilin, European Pharmacopoeia (ep) Reference Standard

75. Equilin, United States Pharmacopeia (usp) Reference Standard

76. Equilin Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

77. (9s,13s,14s)-3-hydroxy-13-methyl-9,11,12,13,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17(14h)-one

78. (9s,13s,14s)-3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro- 6h-cyclopenta[a]phenanthren-17-one

79. Equilin; 7-dehydroestrone; 3-hydroxy-1,3,5(10),7-estratetraen-17-one; 1,3,5(10),7-estratetraen-3-ol-17-one

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₀O₂
Molecular Weight	268.3 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	268.146329876 g/mol
Monoisotopic Mass	268.146329876 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	466
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

For the treatment of moderate to severe vasomotor symptoms associated with the menopause, atrophic vaginitis, osteoporosis, hypoestrogenism due to hypogonadism, castration, primary ovarian failure, breast cancer (for palliation only), and Advanced androgen-dependent carcinoma of the prostate (for palliation only)

5 Pharmacology and Biochemistry

5.1 Pharmacology

Equilin is a component of Premarin (conjugated estrogens), a mixture of the water soluble salts of sulfate esters from estrone, equilin, 17 alpha-dihydroequilin, and other related steroids, may be derived from pregnant equine urine or yam and soy plants. Estrogens are important in the development and maintenance of the female reproductive system and secondary sex characteristics. They promote growth and development of the vagina, uterus, and fallopian tubes, and enlargement of the breasts. Indirectly, they contribute to the shaping of the skeleton, maintenance of tone and elasticity of urogenital structures, changes in the epiphyses of the long bones that allow for the pubertal growth spurt and its termination, growth of axillary and pubic hair, and pigmentation of the nipples and genitals. Decline of estrogenic activity at the end of the menstrual cycle can bring on menstruation, although the cessation of progesterone secretion is the most important factor in the mature ovulatory cycle. However, in the preovulatory or nonovulatory cycle, estrogen is the primary determinant in the onset of menstruation. Estrogens also affect the release of pituitary gonadotropins. The pharmacologic effects of conjugated estrogens are similar to those of endogenous estrogens.

5.2 Absorption, Distribution and Excretion

Absorption

Well absorbed.

5.3 Metabolism/Metabolites

Hepatic

5.4 Mechanism of Action

Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens decrease the secretion of gonadotropin-releasing hormone by the hypothalamus, reducing the secretion of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary.

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