Please Wait
Applying Filters...
Menu
Xls
2D Structure
Also known as: 152-43-2, Estrovis, Estradiol-17-beta 3-cyclopentyl ether, Quinestrolo [dcit], Quinestrolum, Quinestrolum [inn-latin]
Molecular Formula
C25H32O2
Molecular Weight
364.5  g/mol
InChI Key
PWZUUYSISTUNDW-VAFBSOEGSA-N
FDA UNII
JR0N7XD5GZ

The 3-cyclopentyl ether of ETHINYL ESTRADIOL. After gastrointestinal absorption, it is stored in ADIPOSE TISSUE, slowly released, and metabolized principally to the parent compound. It has been used in ESTROGEN REPLACEMENT THERAPY. (From AMA Drug Evaluations Annual, 1992, p1011)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
2.1.2 InChI
InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
2.1.3 InChI Key
PWZUUYSISTUNDW-VAFBSOEGSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
2.2 Other Identifiers
2.2.1 UNII
JR0N7XD5GZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Estrovis

2. Ethinyl Estradiol 3 Cyclopentyl Ether

3. Ethinyl Estradiol 3-cyclopentyl Ether

2.3.2 Depositor-Supplied Synonyms

1. 152-43-2

2. Estrovis

3. Estradiol-17-beta 3-cyclopentyl Ether

4. Quinestrolo [dcit]

5. Quinestrolum

6. Quinestrolum [inn-latin]

7. Estrovister

8. Plestrovis

9. Eston

10. 17-alpha-ethinylestradiol 3-cyclopentyl Ether

11. 17alpha-ethynylestradiol 3-cyclopentyl Ether

12. Qui-lea

13. Eecpe

14. Estrovis 4000

15. W 3566

16. W-3566

17. (8r,9s,13s,14s,17r)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-ol

18. Jr0n7xd5gz

19. Mls000069756

20. Chebi:8716

21. Nsc-759637

22. Ncgc00166146-01

23. Quinestrolo

24. Smr000058815

25. Dsstox_cid_26553

26. Dsstox_rid_81714

27. Dsstox_gsid_46553

28. Quilea

29. 3-o-cyclopentyl-17alpha-ethinyl-estra-1,3,5(10)-triene-3,17beta-diol

30. 17alpha-ethylnyl-1,3,5[10]estratriene-3,17beta-diol 3-cyclopentyl Ether

31. Estrovis (tn)

32. Cas-152-43-2

33. Quinestrol (usan/inn)

34. Einecs 205-803-1

35. Unii-jr0n7xd5gz

36. Quinestriol

37. 3-cyclopentyloxy-17alpha-ethynylestra-1,3,5(10)-trien-17beta-ol

38. Quinestrol [usan:usp:inn:ban]

39. 3-(cyclopentyloxy)-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol

40. Ee2cpe

41. Opera_id_502

42. Quinestrol [mi]

43. Quinestrol [inn]

44. Quinestrol [usan]

45. Quinestrol [vandf]

46. Quinestrol [mart.]

47. Quinestrol [who-dd]

48. Mls001077287

49. Schembl221134

50. Gtpl7097

51. Chembl1201165

52. Dtxsid6046553

53. Quinestrol [orange Book]

54. Hms2235a05

55. 3-(cyclopentyloxy)-17beta-ethynylestra-1,3,5(10)-trien-17-ol

56. Hy-b1012

57. Zinc3875993

58. Ethinylestradiol 3-cyclopentyl Ether

59. Tox21_112340

60. Lmst02010037

61. Mfcd00079189

62. S3671

63. Ethynyl Estradiol-3-cyclopentyl Ether

64. 19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-

65. Akos025310158

66. Tox21_112340_1

67. Ccg-268221

68. Cs-4525

69. Db04575

70. Nsc 759637

71. 19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, (17alpha)-

72. Ncgc00166146-02

73. 17?-ethynylestradiol 3-cyclopentyl Ether

74. As-13038

75. Q0091

76. C07619

77. C72888

78. D00576

79. 152q432

80. A809306

81. Sr-01000759180

82. Q3927871

83. Sr-01000759180-3

84. W-108053

85. 17a-ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-cyclopentyl Ether

86. 3-(cyclopentyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-17.alpha.-ol

87. Estra-1(10),2,4-trien-17-ol, 3-(cyclopentyloxy)-17-ethynyl-, (17)-

88. 19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, 17.alpha.

89. 3-(cyclopentyloxy)-19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yn-17-ol

90. (1s,10r,11s,14r,15s)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-2,4,6-trien-14-ol

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 364.5 g/mol
Molecular Formula C25H32O2
XLogP35.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass364.240230259 g/mol
Monoisotopic Mass364.240230259 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count27
Formal Charge0
Complexity613
Isotope Atom Count0
Defined Atom Stereocenter Count5
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

Used in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Quinestrol is the 3-cyclopentyl ether of ethinyl estradiol (the active metabolite). After gastrointestinal absorption, it is stored in adipose tissue where it is slowly released and metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol.


5.2 MeSH Pharmacological Classification

Estrogens

Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds. (See all compounds classified as Estrogens.)


5.3 Absorption, Distribution and Excretion

Absorption

Absorbed following oral administration.


5.4 Metabolism/Metabolites

Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.


5.5 Mechanism of Action

Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).