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Allylestrenol

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Chemistry

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Also known as: 432-60-0, Gestanin, Gestanon, Allyloestrenol, Gestanol, Orageston

Molecular Formula

C₂₁H₃₂O

Molecular Weight

300.5 g/mol

InChI Key

ATXHVCQZZJYMCF-XUDSTZEESA-N

FDA UNII

I47VB5DZ8O

A synthetic steroid with progestational activity.

1 2D Structure

Allylestrenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

2.1.2 InChI

InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1

2.1.3 InChI Key

ATXHVCQZZJYMCF-XUDSTZEESA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2(CC=C)O)CCC4=CCCCC34

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CCCC[C@H]34

2.2 Other Identifiers

2.2.1 UNII

I47VB5DZ8O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Allyloestrenol

2. Gestanin

3. Gestanon

4. Turinal

2.3.2 Depositor-Supplied Synonyms

1. 432-60-0

2. Gestanin

3. Gestanon

4. Allyloestrenol

5. Gestanol

6. Orageston

7. Turinal

8. Organon

9. Gestanyn

10. Estrenol, Allyl-

11. 17-allylestr-4-en-17-beta-ol

12. 17alpha-allyl-4-estren-17beta-ol

13. 17alpha-allylestr-4-en-17beta-ol

14. Perselin

15. I47vb5dz8o

16. 17.alpha.-allylestr-4-en-17.beta.-ol

17. (8r,9s,10r,13s,14s,17r)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ol

18. Chebi:31189

19. Estr-4-en-17-ol, 17-(2-propenyl)-, (17b)-

20. Nsc-37723

21. 19-norpregn-4-ene-20-yn-17beta-ol

22. Allyloestrenolum

23. 17-alpha-allylestr-4-en-17-beta-ol

24. 17alpha-allylestrenol

25. Allilestrenolo [dcit]

26. Gestanon-r

27. Alilestrenol [inn-spanish]

28. Allylestrenolum [inn-latin]

29. Perselin (tn)

30. 17.alpha.-allylestrenol

31. 17alpha-allyl-4-destrene-17beta-ol

32. 17alpha-allyl-4-oestrene-17beta-ol

33. Allylestrenol (jan/inn)

34. 17-hydroxy-17-alpha-allyl-4-estrene

35. 17-alpha-allyl-4-oestrene-17-beta-ol

36. 17alpha-allyl-17beta-hydroxy-4-estrene

37. Alilestrenol

38. Allilestrenolo

39. Allylestrenolum

40. 17alpha-allyl-3-deoxy-19-nortestosterone

41. Allyl Estrenol

42. 17-alpha-allyl-17-beta-hydroxy-4-estrene

43. Ccris 9068

44. 17-alpha-allyl-3-deoxy-19-nortestosterone

45. 17-alpha-allylhydroxy-19-nor-4-androstene

46. 3-deoxy-17-alpha-allyl-19-nortestosterone

47. Ncgc00159497-02

48. 21-methylene-19-nor-17-alpha-preg-4-en-17-ol

49. Einecs 207-082-9

50. Estr-4-en-17beta-ol, 17-allyl-

51. 17-alpha-allyl-17-beta-hydroxy-delta(sup 4)-estren

52. 17alpha-allyl-19-nor-delta-4-androstene-17beta-ol

53. Nsc 37723

54. Estr-4-en-17-ol, 17-(2-propenyl)-, (17beta)-

55. Brn 3148038

56. 17.alpha.-allyl-4-estren-17.beta.-ol

57. 17.alpha.-allyl-4-destrene-17.beta.-ol

58. 17.alpha.-allyl-4-oestrene-17.beta.-ol

59. Estr-4-en-17-beta-ol, 17-allyl-

60. 17.alpha.-allyl-3-deoxy-19-nortestosterone

61. Dsstox_cid_2574

62. 17.alpha.-allyl-17.beta.-hydroxy-4-estrene

63. Allylestrenol [mi]

64. Unii-i47vb5dz8o

65. Allylestrenol [inn]

66. Allylestrenol [jan]

67. Dsstox_rid_76637

68. (17beta)-17-prop-2-en-1-ylestr-4-en-17-ol

69. Dsstox_gsid_22574

70. Allylestrenol [mart.]

71. Schembl329623

72. 19-nor-17-alpha-preg-4-en-17-ol, 21-methylene-

73. Allylestrenol [who-dd]

74. Allylestrenol [inn:ban:jan]

75. Chembl3185133

76. Dtxsid9022574

77. 17.alpha.-allyl-17-.beta.-hydroxy-.delta.(sup 4)-estren

78. Bcp10809

79. Nsc37723

80. Zinc4214767

81. Tox21_111718

82. Lmst02030125

83. Mfcd00198957

84. S5219

85. Akos015964938

86. Db01431

87. Ds-8255

88. Estr-4-en-17-ol, (17.beta.)-

89. Estr-4-en-17.beta.-ol, 17-allyl-

90. Cas-432-60-0

91. Hy-17375

92. 3-deketo-17alpha-allyl-19-nortestosterone

93. Cs-0006769

94. Wln: L E5 B666 Mutj E1 Fq F2u1

95. D01374

96. 4-06-00-04143 (beilstein Handbook Reference)

97. 432a600

98. Q531965

99. Sr-01000883956

100. Sr-01000883956-1

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₂O
Molecular Weight	300.5 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	300.245315640 g/mol
Monoisotopic Mass	300.245315640 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	492
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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

Allylestrenol was designed to be used for miscarriage prevention, prevention of premature labour and has been investigated for possible use in men for treatment for benign prostatic hyperplasia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Allylestrenol is a progestogen structurally related to progesterone that has been given in threatened and recurrent miscarriage, and to prevent premature labour. However, with the exception of proven progesterone deficiency, such use is no longer recommended. In threatened miscarriage in progesterone-deficient women a suggested dose is 5 mg three times daily by mouth for 5 to 7 days.

5.2 MeSH Pharmacological Classification

Progestins

Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)

5.3 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03D - Progestogens

G03DC - Estren derivatives

G03DC01 - Allylestrenol

5.4 Absorption, Distribution and Excretion

Route of Elimination

The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.

5.5 Mechanism of Action

Allylestrenol is similar in structure and function to progesterone. Progesterone shares the pharmacological actions of the progestins. Progesterone 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 Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity.

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API Reference Price

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