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2D Structure
Also known as: 297-76-7, Femulen, Continuin, Ethinodiol diacetate, Etynodiol acetate, Etynodiol diacetate
Molecular Formula
C24H32O4
Molecular Weight
384.5  g/mol
InChI Key
ONKUMRGIYFNPJW-KIEAKMPYSA-N
FDA UNII
62H10A1236

A synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive (CONTRACEPTIVES, ORAL).
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
2.1.2 InChI
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
2.1.3 InChI Key
ONKUMRGIYFNPJW-KIEAKMPYSA-N
2.1.4 Canonical SMILES
CC(=O)OC1CCC2C3CCC4(C(C3CCC2=C1)CCC4(C#C)OC(=O)C)C
2.1.5 Isomeric SMILES
CC(=O)O[C@H]1CC[C@@H]2[C@H]3CC[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(C#C)OC(=O)C)C
2.2 Other Identifiers
2.2.1 UNII
62H10A1236
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (3 Beta, 17 Alpha)-19-norpregn-4-en-20-yne-3,17 Diol Diacetate

2. 19-norpregn-4-en-20-yne-3,17-diol, Diacetate, (3beta,17alpha)-

3. Continuin

4. Ethyndiol Diacetate

5. Ethynodiol Diacetate, (17 Alpha)-isomer

6. Femulen

2.3.2 Depositor-Supplied Synonyms

1. 297-76-7

2. Femulen

3. Continuin

4. Ethinodiol Diacetate

5. Etynodiol Acetate

6. Etynodiol Diacetate

7. Cervicundin

8. Metrodiol

9. Luto-metrodiol

10. Metrodiol Diacetate

11. Sc 11800

12. Ovulen 50

13. Sc-11800

14. 19-nor-17alpha-pregn-4-en-20-yne-3beta,17-diol Diacetate

15. 17a-ethynyl-4-estren-3b,17-diol Diacetate

16. Chebi:31580

17. Ethynodiol Acetate

18. (3beta,17beta)-17-ethynylestr-4-ene-3,17-diyl Diacetate

19. [(3s,8r,9s,10r,13s,14s,17r)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] Acetate

20. 17alpha-ethynyl-3,17-dihydroxy-4-estrene Diacetate

21. 17alpha-ethynylestr-4-ene-3beta,17beta-diol Acetate

22. 3beta, 17beta-diacetoxy-17alpha-ethynyl-4-oestrene

23. 17alpha-ethynyl-4-estrene-3beta,17beta-diol Diacetate

24. Nsc-759288

25. (3s,8r,9s,10r,13s,14s,17r)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,17-diyl Diacetate

26. Ethynodiol (diacetate)

27. Ncgc00166138-01

28. 3beta,17beta-diacetoxy-19-nor-17alpha-pregn-4-en-20-yne

29. Etynodiol Di(acetate)

30. 17alpha-ethynyl-19-norandrost-4-ene-3beta,17-beta-diol Diacetate

31. Dsstox_cid_614

32. 62h10a1236

33. Dsstox_rid_75690

34. Dsstox_gsid_20614

35. Ethynodiol Diacetate [usan]

36. 19-norpregn-4-en-20-yn-3beta,17alpha-diol, Diacetate

37. Ccris 305

38. 8080 C. B.

39. Ethynodiol Diacetate [progestins]

40. Einecs 206-044-9

41. 17-alpha-ethynyl-3,17-dihydroxy-4-estrene Diacetate

42. 3-beta, 17-beta-diacetoxy-17-alpha-ethynyl-4-oestrene

43. 17-alpha-ethynylestr-4-ene-3-beta,17-beta-diol Acetate

44. 17-alpha-ethynyl-4-estrene-3-beta,17-beta-diol Diacetate

45. 19-norpregn-4-en-20-yne-3,17-diol, Diacetate, (3.beta.,17.alpha.)-

46. Ethynodiol Diacetate (jan/usp)

47. 3-beta,17-beta-diacetoxy-19-nor-17-alpha-pregn-4-en-20-yne

48. Ethynodiol Diacetate [usan:usp]

49. (3-beta,17-alpha)-19-norpregn-4-en-20-yne-3,17-diol Diacetate

50. 17-alpha-ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol Diacetate

51. Unii-62h10a1236

52. Ncgc00186466-01

53. Ethynodiol-diacetate

54. Cas-297-76-7

55. 19-nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol Diacetate

56. Prestwick0_000908

57. Prestwick1_000908

58. Prestwick2_000908

59. Prestwick3_000908

60. Schembl40888

61. Bspbio_000756

62. Mls000028661

63. Spbio_002955

64. 17alpha-ethynylestr-4-ene-3beta,17beta-diyl Diacetate

65. Bpbio1_000832

66. Gtpl7072

67. Chembl1200624

68. Dtxsid4020614

69. Ethynodiol Diacetate [mi]

70. Ethynodiol Diacetate [jan]

71. Hms1570f18

72. Hms2097f18

73. Hms3714f18

74. Bcp10923

75. Etynodiol Diacetate [mart.]

76. Hy-b1089

77. Zinc3876023

78. Tox21_112333

79. Tox21_112924

80. Bdbm50237627

81. Etynodiol Diacetate [who-dd]

82. Lmst02030124

83. Mfcd00083326

84. S3160

85. Ethynodiol Diacetate [usp-rs]

86. Akos015895252

87. Tox21_112333_1

88. 8080 Cb

89. Ccg-220908

90. Cs-4640

91. Db00823

92. Nsc 759288

93. Ncgc00166138-02

94. Ncgc00166138-03

95. Ncgc00166138-04

96. Ncgc00166138-05

97. As-13382

98. Ethynodiol Diacetate [orange Book]

99. Smr000058858

100. Ethynodiol Diacetate [usp Impurity]

101. Zovia Component Ethynodiol Diacetate

102. Ethynodiol Diacetate [usp Monograph]

103. Kelnor Component Ethynodiol Diacetate

104. Ovulen Component Ethynodiol Diacetate

105. Ab00513958

106. B1508

107. E1315

108. D01294

109. Ethynodiol Diacetate Component Of Kelnor

110. Ethynodiol Diacetate Component Of Ovulen

111. T72249

112. Ab00513958_02

113. 297e767

114. A820050

115. Sr-01000872687

116. J-017631

117. Q5405160

118. Sr-01000872687-1

119. 19-norpregn-4-en-20-yne-3,17-diol, Diacetate, (3b,17a)-

120. (3beta, 17alpha)-19-norpregn-4-en-20-yne-3,17-diol Diacetate

121. Ethynodiol Diacetate, United States Pharmacopeia (usp) Reference Standard

122. [(3s,8r,9s,10r,13s,14s,17r)-17-acetoxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] Acetate;ethynodiol Diacetate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 384.5 g/mol
Molecular Formula C24H32O4
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass384.23005950 g/mol
Monoisotopic Mass384.23005950 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count28
Formal Charge0
Complexity758
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

For the prevention of pregnancy in women who elect to use this product as a method of contraception.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ethynodiol Diacetate is used as a female contraceptive. Ethynodiol Diacetate is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Ethynodiol Diacetate tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.


5.2 MeSH Pharmacological Classification

Contraceptives, Oral, Hormonal

Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)


Contraceptives, Oral, Synthetic

Oral contraceptives which owe their effectiveness to synthetic preparations. (See all compounds classified as Contraceptives, Oral, Synthetic.)


5.3 Mechanism of Action

Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.