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Prestwick3_000105
Also known as: Danocrine, 17230-88-5, Chronogyn, Winobanin, Danol, Cyclomen
Molecular Formula
C22H27NO2
Molecular Weight
337.5  g/mol
InChI Key
POZRVZJJTULAOH-LHZXLZLDSA-N
FDA UNII
N29QWW3BUO

A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.
Danazol is an Androgen. The mechanism of action of danazol is as an Androgen Receptor Agonist.
1 2D Structure

Prestwick3_000105

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
2.1.2 InChI
InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
2.1.3 InChI Key
POZRVZJJTULAOH-LHZXLZLDSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C#C)O)CCC4=CC5=C(CC34C)C=NO5
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
2.2 Other Identifiers
2.2.1 UNII
N29QWW3BUO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Azol

2. Cyclomen

3. Danatrol

4. Danazant

5. Danazol Ratiopharm

6. Danazol-ratiopharm

7. Danocrine

8. Danol

9. Danoval

10. Ladogal

11. Norciden

12. Panacrine

2.3.2 Depositor-Supplied Synonyms

1. Danocrine

2. 17230-88-5

3. Chronogyn

4. Winobanin

5. Danol

6. Cyclomen

7. Danazolum

8. Ladogal

9. Danzol

10. Danatrol

11. Danazol, Usp

12. Win-17757

13. Win 17,757

14. Danazole

15. N29qww3buo

16. (1r,3as,3br,10ar,10bs,12as)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1h-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol

17. Win 17757

18. Danovaol

19. Chebi:4315

20. Danokrin

21. Nsc-270916

22. Ncgc00164400-01

23. Danogen

24. Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol, (17alpha)-

25. Dsstox_cid_2880

26. Danazolum [inn-latin]

27. Nsc 270916

28. Dsstox_rid_76772

29. Dsstox_gsid_22880

30. Bonzol

31. Danocrine (tn)

32. Smr000058321

33. Ccris 6747

34. Einecs 241-270-1

35. Unii-n29qww3buo

36. Vasaloc

37. 17-alpha-pregn-4-en-20-yno(2,3-d)isoxazol-17-ol

38. Optina

39. Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17alpha)-

40. 17-alpha-2,4-pregnadien-20-yno(2,3-d)isoxazol-17-ol

41. 17alpha-pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol

42. Nsc270916

43. Win 17, 757

44. Prestwick_150

45. Cas-17230-88-5

46. Danazol [usan:usp:inn:ban:jan]

47. Danazol [vandf]

48. Ethynyl(dimethyl)[?]ol

49. 2,3-isoxazolethisterone

50. Danazol [usan]

51. Danazol [inn]

52. Danazol [jan]

53. Danazol [mi]

54. Danazol [mart.]

55. Prestwick0_000105

56. Prestwick1_000105

57. Prestwick2_000105

58. Prestwick3_000105

59. Danazol [usp-rs]

60. Danazol [who-dd]

61. Chembl1479

62. Schembl21107

63. Bspbio_000090

64. (1s,2r,13r,14s,17r,18s)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol

65. Mls001066617

66. Mls001306473

67. Danazol (jp17/usp/inn)

68. Danazol [orange Book]

69. Spbio_002029

70. Bpbio1_000100

71. Gtpl6942

72. Danazol [usp Monograph]

73. Dtxsid2022880

74. 2,4,17alpha-pregnadien-20-yno[2,3-d]-isoxa-zol-17-ol

75. Win-17,757

76. Hms1568e12

77. Hms2090a22

78. Hms2095e12

79. Hms2231m08

80. Hms3259m10

81. Hms3712e12

82. Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol,(17alpha)-

83. [1,2]oxazolo[4',5':2,3]-17alpha-pregn-4-en-20-yn-17-ol

84. 17.alpha.-pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol}

85. Bcp11914

86. Hy-b1029

87. Zinc3881958

88. Tox21_112114

89. Tox21_301940

90. Bdbm50423541

91. Mfcd00056838

92. S9506

93. Akos015961192

94. Tox21_112114_1

95. Ac-6836

96. Ccg-220105

97. Cs-4547

98. Danazol 100 Microg/ml In Acetonitrile

99. Db01406

100. Nc00557

101. Ncgc00179665-01

102. Ncgc00179665-02

103. Ncgc00179665-04

104. Ncgc00255335-01

105. (1r,3as,3br,10ar,10bs,12as)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1h-cyclopenta[7,8]phenanthro[3,2-d][1,2]oxazol-1-ol

106. 1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1h-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol

107. As-13035

108. C06938

109. D00289

110. 230d885

111. Q419652

112. Sr-01000760722

113. Sr-05000000445

114. Sr-01000760722-2

115. Sr-05000000445-2

116. W-107864

117. 17a-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol

118. Brd-k48970916-001-03-0

119. (17a)-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol

120. 17a-pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol

121. 1-(p-tosyl)-3,4,4-trimethyl-2-imidazoliniumiodide

122. 17 Alpha-pregna-2,4-dien-20-yno[2,3-d] Isoxazol-17 Beta-ol

123. 17.alpha.-pregna-2,4-dien-20-yno(2,3)-disoxazol-17-ol

124. Pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol,} (17.alpha.)-

125. Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol,(17.alpha.)-

126. (1s,2r,13r,14s,17r,18s)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol

127. 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1h-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol

128. 1h-cyclopenta[7,8]phenanthro[3,2-d]isoxazole- Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol Deriv.

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 337.5 g/mol
Molecular Formula C22H27NO2
XLogP33.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass337.204179104 g/mol
Monoisotopic Mass337.204179104 g/mol
Topological Polar Surface Area46.3 Ų
Heavy Atom Count25
Formal Charge0
Complexity677
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDanazol
PubMed HealthDanazol (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelDanazol is a synthetic steroid derived from ethisterone. It is a white to pale yellow crystalline powder, practically insoluble or insoluble in water, and sparingly soluble in alcohol. Chemically, danazol is 17-Pregna-2, 4-dien-20-yno [2, 3- ]-isox...
Active IngredientDanazol
Dosage FormCapsule
RouteOral
Strength200mg; 100mg; 50mg
Market StatusPrescription
CompanyLannett; Barr

2 of 2  
Drug NameDanazol
PubMed HealthDanazol (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelDanazol is a synthetic steroid derived from ethisterone. It is a white to pale yellow crystalline powder, practically insoluble or insoluble in water, and sparingly soluble in alcohol. Chemically, danazol is 17-Pregna-2, 4-dien-20-yno [2, 3- ]-isox...
Active IngredientDanazol
Dosage FormCapsule
RouteOral
Strength200mg; 100mg; 50mg
Market StatusPrescription
CompanyLannett; Barr

4.2 Drug Indication

For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.


5.2 MeSH Pharmacological Classification

Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DANAZOL
5.3.2 FDA UNII
N29QWW3BUO
5.3.3 Pharmacological Classes
Androgen [EPC]; Androstanes [CS]; Androgen Receptor Agonists [MoA]
5.4 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03X - Other sex hormones and modulators of the genital system

G03XA - Antigonadotropins and similar agents

G03XA01 - Danazol


5.5 Metabolism/Metabolites

Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.


5.6 Biological Half-Life

Approximately 24 hours.


5.7 Mechanism of Action

As a gonadotropin inhibitor, danazol suppresses the pituitary-ovarian axis possibly by inhibiting the output of pituitary gonadotropins. Danazol also depresses the preovulatory surge in output of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibits ovarian steroidogenesis; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex-hormone-binding globulin and corticosteroid-binding globulin; and increases the metabolic clearance rate of progesterone. Another mechanism of action by which danazol may use to facilitate regression of endometriosis is by decreasing IgG, IgM, and IgA concentrations, as well as phospholipid and IgG isotope autoantibodies. In the treatment of endometriosis, as a consequence of suppression of ovarian function, danazol causes both normal and ectopic endometrial tissues to become inactive and atrophic. This leads to anovulation and associated amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unknown, but may be related to suppressed estrogenic stimulation as a result of decreased ovarian production of estrogen. A direct effect on steroid receptor sites in breast tissue is also possible. This leads to a disappearance of nodularity, relief of pain and tenderness, and possibly changes in the menstrual pattern. In terms of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing serum concentrations of the deficient C1 esterase inhibitor, resulting in increased serum concentrations of the C4 component of the complement system. (Source: PharmGKB)


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