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Chemistry

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Also known as: 76-43-7, Fluoxymestrone, Halotestin, Fluoximesterone, Androfluorene, Androfluorone
Molecular Formula
C20H29FO3
Molecular Weight
336.4  g/mol
InChI Key
YLRFCQOZQXIBAB-RBZZARIASA-N
FDA UNII
9JU12S4YFY

Fluoxymesterone
An anabolic steroid that has been used in the treatment of male HYPOGONADISM, delayed puberty in males, and in the treatment of breast neoplasms in women.
Fluoxymesterone is an Androgen. The mechanism of action of fluoxymesterone is as an Androgen Receptor Agonist.
1 2D Structure

Fluoxymesterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
2.1.3 InChI Key
YLRFCQOZQXIBAB-RBZZARIASA-N
2.1.4 Canonical SMILES
CC12CCC(=O)C=C1CCC3C2(C(CC4(C3CCC4(C)O)C)O)F
2.1.5 Isomeric SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3CC[C@]4(C)O)C)O)F
2.2 Other Identifiers
2.2.1 UNII
9JU12S4YFY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Android F

2. Android-f

3. Fluoximesteron

4. Halotestin

5. Stenox

2.3.2 Depositor-Supplied Synonyms

1. 76-43-7

2. Fluoxymestrone

3. Halotestin

4. Fluoximesterone

5. Androfluorene

6. Androfluorone

7. Fluotestin

8. Android-f

9. Ora-testryl

10. Androsterolo

11. Fluosterone

12. Flusteron

13. Flutestos

14. Oralsterone

15. Oratestin

16. Testoral

17. Ultandren

18. Ultandrene

19. Fluoximesteronum

20. Neo-ormonal

21. Ora Testryl

22. Fluoximesterona

23. Fluossimesterone [dcit]

24. Fluoxymesteronum

25. Fluoxymesteronum [inn-latin]

26. Fluoximesterona [inn-spanish]

27. Nsc-12165

28. Fluoxymesteron

29. (8s,9r,10s,11s,13s,14s,17s)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

30. 9alpha-fluoro-11beta-hydroxy-17-methyltestosterone

31. Fluoxymesterone Ciii

32. U 6040

33. 9-fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one

34. Nsc 10704

35. Nsc-10704

36. Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-

37. 9ju12s4yfy

38. Chebi:5120

39. Fxm

40. Anadroid-f

41. (11beta,17beta)-9-fluoro-11,17-dihydroxy-17-methylandrost-4-en-3-one

42. 17alpha-methyl-9alpha-fluoro-11beta-hydroxytesterone

43. Component Of Halodrin

44. Fluossimesterone

45. 11beta,17beta-dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one

46. Dsstox_cid_13512

47. Dsstox_rid_79080

48. Dsstox_gsid_33512

49. 9.alpha.-fluoro-11.beta.-hydroxy-17-methyltestosterone

50. Androxy

51. 9alpha-fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one

52. 9.alpha.-fluoro-11.beta.,17.beta.-dihydroxy-17.alpha.-methyl-4-androstene-3-one

53. Cas-76-43-7

54. Halotestin (tn)

55. (8s,9r,10s,11s,13s,14s,17s)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

56. Ccris 9036

57. Hsdb 3333

58. Einecs 200-961-8

59. Testosterone, 9-fluoro-11.beta.-hydroxy-17-methyl-

60. Unii-9ju12s4yfy

61. Brn 2008796

62. 9-alpha-fluoro-11-beta-hydroxy-17-methyltestosterone

63. 17-alpha-methyl-9-alpha-fluoro-11-beta-hydroxytesterone

64. Ai3-52940

65. 9-fluoro-11-beta,17-beta-dihydroxy-17-methylandrost-4-en-3-one

66. Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11.beta.,17.beta.)-

67. 9alpha-fluoro-17alpha-methyl-11beta,17-dihydroxy-4-androsten-3-one

68. Ncgc00182970-01

69. 11beta,17beta-dihydroxy-9alpha-fluoro-17alpha-methyl-4-androsten-3-one

70. 9-alpha-fluoro-17-alpha-methyl-11-beta,17-dihydroxy-4-androsten-3-one

71. 9alpha-fluoro-11beta,17beta-dihydroxy-17alpha-methyl-4-androstene-3-one

72. Androxy (tn)

73. 11-beta,17-beta-dihydroxy-9-alpha-fluoro-17-alpha-methyl-4-androster-3-one

74. 9-alpha-fluoro-11-beta,17-beta-dihydroxy-17-alpha-methyl-4-androstene-3-one

75. Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11beta,17beta)-

76. Fluoxymesterone [usp:inn:ban:jan]

77. Fluoro-9-alpha Dihydroxy-11-beta,17-beta Methyl-17-alpha Androstene-4 One-3 [french]

78. Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-

79. Fluoro-9-alpha Dihydroxy-11-beta,17-beta Methyl-17-alpha Androstene-4 One-3

80. Schembl5096

81. Chembl1445

82. Fluoxymesterone [mi]

83. Fluoxymesterone [inn]

84. Fluoxymesterone [jan]

85. 4-08-00-02057 (beilstein Handbook Reference)

86. Mls001055414

87. Fluoxymesterone [hsdb]

88. Fluoxymesterone [vandf]

89. Gtpl2861

90. Fluoxymesterone [mart.]

91. Dtxsid8033512

92. Fluoxymesterone [who-dd]

93. Bdbm18189

94. Fluoxymesterone (jan/usp/inn)

95. Hms2272b06

96. Bcp10776

97. Nsc10704

98. Nsc12165

99. Zinc3875484

100. Tox21_113158

101. Tox21_200854

102. 9-fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one

103. Fluoxymesterone [orange Book]

104. Lmst02020025

105. Fluoxymesterone Ciii [usp-rs]

106. Akos015895109

107. Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl- (van)

108. Db01185

109. Fluoxymesterone [usp Monograph]

110. Fluoxymesterone, Solid (photosensitive)

111. Ncgc00091037-01

112. Ncgc00091037-02

113. Ncgc00258408-01

114. Ac-29744

115. Smr000686158

116. Fluoxymesterone 1.0 Mg/ml In Acetonitrile

117. D00327

118. 010f480

119. A838701

120. Q410663

121. W-104363

122. 9-fluoro-11.beta.,17.beta.-dihydroxy-17-methylandrost-4-en-3-one

123. (1r,2s,10s,11s,14s,15s,17s)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one

124. (8s,9r,10s,11s,13s,14s,17s)-9-fluoranyl-10,13,17-trimethyl-11,17-bis(oxidanyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 336.4 g/mol
Molecular Formula C20H29FO3
XLogP32.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass336.21007294 g/mol
Monoisotopic Mass336.21007294 g/mol
Topological Polar Surface Area57.5 Ų
Heavy Atom Count24
Formal Charge0
Complexity630
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 Information
1 of 2  
Drug NameFluoxymesterone
PubMed HealthFluoxymesterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Hematopoietic
Drug LabelHALOTESTIN Tablets contain fluoxymesterone, an androgenic hormone.Fluoxymesterone is a white or nearly white, odorless, crystalline powder, melting at or about 240 C, with some decomposition. It is practically insoluble in water, sparingly soluble...
Active IngredientFluoxymesterone
Dosage FormTablet
RouteOral
Strength10mg
Market StatusPrescription
CompanyUsl Pharma

2 of 2  
Drug NameFluoxymesterone
PubMed HealthFluoxymesterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Hematopoietic
Drug LabelHALOTESTIN Tablets contain fluoxymesterone, an androgenic hormone.Fluoxymesterone is a white or nearly white, odorless, crystalline powder, melting at or about 240 C, with some decomposition. It is practically insoluble in water, sparingly soluble...
Active IngredientFluoxymesterone
Dosage FormTablet
RouteOral
Strength10mg
Market StatusPrescription
CompanyUsl Pharma

4.2 Therapeutic Uses

Anabolic Steroids; Antineoplastic Agents, Hormonal

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Androgens are primarily indicated in males as replacement therapy when congenital or acquired endogenous androgen absence or deficiency is associated with primary hypogonadal or secondary hypogonadism. Primary hypogonadism includes conditions such as testicular failure due to cryptorchidism, bilateral torsion, orchitis, or vanishing testis syndrome; inborn errors in testosterone biosynthesis; or bilateral orchidectomy. Hypogonadotropic hypogonadism (secondary hypogonadism) conditions include gonadotropin releasing hormone (GnRH) deficiency; or pituitary hypothalamic injury as a result of surgery, tumors, trauma, or radiation and are the most common forms of hypogonadism seen in older adults. Dosage adjustment is needed to accommodate individual clinical requirements for such life changes as induction of puberty, development of secondary sexual characteristics, impotence due to testicular failure, or infertility due to oligospermia.. /Androgens; Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 150


A 6 month or shorter course of an androgen is indicated for induction of puberty in patients with familial delayed puberty, a condition characterized by spontaneous, nonpathologic, late-onset puberty, if the patient does not respond to psychological treatment. /Androgens; Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


Androgens are used in the treatment of constitutional delay in growth. However, they are not longer considered the treatment of choice for most patients. /Androgens; NOT included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


For more Therapeutic Uses (Complete) data for FLUOXYMESTERONE (9 total), please visit the HSDB record page.


4.3 Drug Warning

FDA Pregnancy Risk Category: X /CONTRAINDICATED IN PREGNANCY. Studies in animals or humans, or investigational or post-marketing reports, have demonstrated positive evidence of fetal abnormalities or risk which clearly outweights any possible benefit to the patient./

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 153


Cholestatic hepatitis and jaundice and abnormal liver function test results may occur in patients receiving 17-alpha-alkylandrogens such as fluoxymesterone. These adverse hepatic effects may occur at relatively low doses of the drug. Drug-induced jaundice usually is reversible following discontinuance of the drug. Fluoxymesterone should be discontinued if cholestatic jaundice or hepatitis occurs, or if liver function test results become abnormal during therapy with the drug; the etiology of these disorders should be determined. Peliosis of the liver and hepatocellular neoplasms, including hepatocellular adenoma and carcinoma, have been reported rarely in patients receiving long-term administration of androgenic anabolic steroids. Peliosis of the liver can be a life-threatening or fatal complication of androgen therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2946


Fluoxymesterone is contraindicated in males with carcinoma of the breast or known or suspected carcinoma of the prostate. The manufacturers state that the drug also is contraindicated in patients with serious cardiac, renal, or hepatic disease and in patients with known hypersensitivity to the drug. Because of the potential risk of serious adverse health effects, fluoxymesterone should not be used for enhancement of athletic performance or physique.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2946


Use of androgens to enhance athletic performance is illegal. Increases in muscle mass and muscle strength can be sufficient to enhance athletic performance. However, the risk of unwanted effects, such as suppression of spermatogenesis, testicular atrophy, menstrual disturbances, virilization in females, peliosis hepatis (hepatic parenchymal injury), hepatotoxicity, potential adverse effects on cardiovascular health, and development of hepatic cancer, counter athletic benefits received from androgens and make their use in athletes inappropriate. Furthermore, behavioral disturbances, including aggressive or violent behavior, have been reported with supraphysiological self-administered doses in athletics. /Androgens/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


For more Drug Warnings (Complete) data for FLUOXYMESTERONE (20 total), please visit the HSDB record page.


4.4 Drug Indication

In males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fluoxymesterone is a synthetic androgen, or male hormone, similar to testosterone. Fluoxymesterone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.


5.2 MeSH Pharmacological Classification

Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FLUOXYMESTERONE
5.3.2 FDA UNII
9JU12S4YFY
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Androstanes
5.4 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03B - Androgens

G03BA - 3-oxoandrosten (4) derivatives

G03BA01 - Fluoxymesterone


5.5 Absorption, Distribution and Excretion

Absorption

Oral absorption is less than 44%.


It is not known whether fluoxymesterone is distributed into milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2946


Less than 5% is excreted in urine as free steroid and glucuronide conjugate over a 24 hour period after doses of 20 to 200 mg.

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 153


5.6 Metabolism/Metabolites

Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver


Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration.

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 152


5.7 Biological Half-Life

9.2 hours


Approximately 9.2 hours

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 152


5.8 Mechanism of Action

Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.


Androgens are highly lipid-soluble and enter cells of target tissues by passive diffusion. Testosterone or 5-alpha-dihydrotestosterone (DHT), a metabolite produced from testosterone by the enzyme 5-alpha-reductase, binds to an intracellular androgen receptor. The hormone receptor complex translocates into the nucleus and attaches to specific hormone receptor elements on the chromosome to initiate or suppress transcription and protein synthesis. Testosterone can produce estrogenic effects as a result of its conversion to estrogen. /Androgens/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


Exogenous administration of androgens inhibits the release of endogenous testosterone via feedback inhibition of pituitary luteinizing hormone (LH). Following administration of large doses of exogenous androgens, spermatogenesis also may be suppressed as a result of feedback inhibition of pituitary follicle-stimulating hormone (FSH). Androgens reportedly stimulate the production of erythrocytes, apparently by enhancing the production of erythropoietic stimulating factor. /Androgens/

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2946


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