1. Anadrol
2. Anapolon 50
3. Hydroxymetholone
4. Oxymethalone
5. Oxymetholone, (17 Beta)-isomer
6. Oxymetholone, (5 Alpha,17 Alpha)-isomer
1. 434-07-1
2. Anapolon
3. Anasteron
4. Nastenon
5. Protanabol
6. Anadrol
7. Anadrol-50
8. Oximetolona
9. Adroyd
10. Oxymethenolone
11. Adroidin
12. Plenastril
13. Synasteron
14. Roboral
15. Oximetholonum
16. Oxymetholonum
17. Anadroyd
18. Becorel
19. Dynasten
20. Methabol
21. Pardroyd
22. Pavisoid
23. Zenalosyn
24. Ci-406
25. Oxitosona-50
26. Oxymethalone
27. Oximetholone
28. Nsc-26,198
29. Oxymetholone Ciii
30. Anasterone
31. Hmd
32. 2-hydroxymethylene-17alpha-methyldihydrotestosterone
33. L76t0zca8k
34. 4,5alpha-dihydro-2-hydroxymethylene-17alpha-methyltestosterone
35. 17alpha-methyl-2-hydroxymethylene-17-hydroxy-5alpha-androstan-3-one
36. 2-hydroxymethylene-17alpha-methyl-5alpha-androstan-17beta-ol-3-one
37. 17-hydroxy-2-(hydroxymethylene)-17-methyl-5-alpha-17-beta-androst-3-one
38. 17beta-hydroxy-2-(hydroxymethylene)-17-methyl-5alpha-androstan-3-one
39. 2-hydroxymethylene-17alpha-methyl-17beta-hydroxy-5alpha-androstan-3-one
40. Nsc-26198
41. Ncgc00091430-01
42. Oximetalonu
43. 17-beta-hydroxy-2-hydroxymethylene-17-alpha-methyl-3-androstanone
44. Dsstox_gsid_23794
45. Anapolon 50
46. (2z,5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
47. Ossimetolone [dcit]
48. Ossimetolone
49. 17-hydroxy-2-(hydroxymethylene)-17-methyl-5-androstan-3-one
50. Oximetolona [inn-spanish]
51. Oxymetholonum [inn-latin]
52. (5s,8r,9s,10s,13s,14s,17s,z)-17-hydroxy-2-(hydroxymethylene)-10,13,17-trimethyltetradecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one
53. Cas-434-07-1
54. Ccris 492
55. Dsstox_cid_3794
56. Hsdb 3374
57. Dsstox_rid_77193
58. Einecs 207-098-6
59. Ci 406
60. 17-hydroxy-5-alpha-androstan-3-one
61. Unii-l76t0zca8k
62. Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5.alpha.,17.beta.)-
63. 2-hydroxymethylene-17-alpha-methyl-dihydrotestosterone
64. Anadrol-50 (tn)
65. Oxymetholone [usan:usp:inn:ban:jan]
66. 2-hydroxymethylene-17alpha-methylandrostan-17beta-ol-3-one
67. 4,5-dihydro-2-hydroxymethylene-17-alpha-methyltestosterone
68. 2-hydroxymethylene-17alpha-methyl-17beta-hydroxy-3-adrostanone
69. 2-hydroxymethylene-17-alpha-methyl-17-beta-hydroxy-3-androstanone
70. Oxymetholone [mi]
71. Oxymetholone [androgenic Steroids, Anabolic]
72. 17-alpha-methyl-2-hydroxymethylene-17-hydroxy-5-alpha-androstan-3-one
73. 2-hydroxymethylene-17-alpha-methyl-5-alpha-androstan-17-beta-ol-3-one
74. 5alpha-androstan-3-one, 17beta-hydroxy-2-(hydroxymethylene)-17-methyl-
75. Oxymetholone [inn]
76. Oxymetholone [jan]
77. 17-beta-hydroxy-2-(hydroxymethylene)-17-alpha-methyl-5-alpha-androstan-3-one
78. Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (alpha,17beta)-
79. Oxymetholone [hsdb]
80. Oxymetholone [usan]
81. Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5alpha,17beta)-
82. Oxymetholone [vandf]
83. Oxymetholone [mart.]
84. Oxymetholone [who-dd]
85. Schembl145158
86. Schembl145160
87. Chebi:7864
88. Chembl1200585
89. Chembl1578149
90. Dtxsid5023794
91. Niosh/bv8059400
92. Oxymetholone (jp17/usp/inn)
93. Oxymetholone [orange Book]
94. Oxymetholone Ciii [usp-rs]
95. (1s,2s,4z,7s,10r,11s,14s,15s)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
96. Oxymetholone [usp Monograph]
97. Tox21_111131
98. Tox21_200071
99. Bdbm50248303
100. 5-alpha,17-beta-androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-
101. 5-alpha-androstan-3-one, 17-beta-hydroxy-2-(hydroxymethylene)-17-methyl-
102. Akos027473312
103. Androstano(2,3-c)(1,2,5)oxadiazol-17-ol, 17-methyl-, (5-alpha,17-beta)-
104. Tox21_111131_1
105. Zinc118912450
106. Db06412
107. Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5-alpha,17-beta)-
108. Ncgc00091430-02
109. Ncgc00257625-01
110. Ncgc00263581-01
111. Ns-05498
112. Stanozolol Impurity B [ep Impurity]
113. Bv80594000
114. C07393
115. D00490
116. Ab01566927_01
117. Q420864
118. W-106231
119. 2-hydroxymethyleneandrostan-17-beta-ol-17-alpha-methyl-3-one
120. 17beta-hydroxy-2-hydroxymethylidene-17alpha-methyl-3-androstanone
121. 17alpha-methyl-2-hydroxymethylene-17beta-hydroxy-5alpha-androstan-3-one
122. 17beta-hydroxy-2-(hydroxymethylidene)-17-methyl-5alpha-androstan-3-one
123. Androstan-3-one, 17-beta-hydroxy-2-(hydroxymethylene)-17-alpha-methyl-
124. (2z,5alpha,17beta)-17-hydroxy-2-(hydroxymethylene)-17-methylandrostan-3-one
125. (5alpha,17beta)-17-hydroxy-2-(hydroxymethylidene)-17-methylandrostan-3-one
126. 17.beta.-hydroxy-2-(hydroxymethylene)-17-methyl-5.alpha.-androstan-3-one
127. (1s,3as,3br,5as,8z,9as,9bs,11as)-1-hydroxy-8-(hydroxymethylidene)-1,9a,11a-trimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-7-one
128. (5s,8r,9s,10s,13s,14s,17s,z)-17-hydroxy-2-(hydroxymethylene)-10,13,17-trimethylhexadecahydro-3h-cyclopenta[a]phenanthren-3-one
129. 78964-17-7
130. Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (2z,5.alpha.,17.beta.)-
| Molecular Weight | 332.5 g/mol |
|---|---|
| Molecular Formula | C21H32O3 |
| XLogP3 | 4.4 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 332.23514488 g/mol |
| Monoisotopic Mass | 332.23514488 g/mol |
| Topological Polar Surface Area | 57.5 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 596 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Anadrol-50 |
| PubMed Health | Oxymetholone (By mouth) |
| Drug Classes | Endocrine-Metabolic Agent, Hematopoietic |
| Drug Label | Anadrol-50 (oxymetholone) Tablets for oral administration each contain 50 mg of the steroid oxymetholone, a potent anabolic and androgenic drug.The chemical name for oxymetholone is 17-hydroxy-2-(hydroxymethylene)-17-methyl-5-androstan-3-one. T... |
| Active Ingredient | Oxymetholone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 50mg |
| Market Status | Prescription |
| Company | Meda Pharms |
| 2 of 2 | |
|---|---|
| Drug Name | Anadrol-50 |
| PubMed Health | Oxymetholone (By mouth) |
| Drug Classes | Endocrine-Metabolic Agent, Hematopoietic |
| Drug Label | Anadrol-50 (oxymetholone) Tablets for oral administration each contain 50 mg of the steroid oxymetholone, a potent anabolic and androgenic drug.The chemical name for oxymetholone is 17-hydroxy-2-(hydroxymethylene)-17-methyl-5-androstan-3-one. T... |
| Active Ingredient | Oxymetholone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 50mg |
| Market Status | Prescription |
| Company | Meda Pharms |
Anabolic Steroids; Carcinogens
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
Oxymetholone is a synthetic anabolic-androgenic steroid hormone having actions similar to those of the male hormone testosterone. It is used primarily in clinical therapy to maintain a positive nitrogen balance. It can be used to reverse excess excretion of calcium and nitrogen resulting from corticosteroid therapy, prolonged immobilization, and other diseases characterized by catabolism and tissue depletion. It is used to promote weight gain, to counteract weakness and emaciation resulting from debilitating diseases, and after serious infections, burns, trauma, or surgery. It is marketed as a human prescription drug for the treatment of anemias caused by deficient red cell production.
DHHS/NIEHS; Seventh Annual Rpt on Carcinogens Summary p. 313 (1994)
Anabolic steroids have been used for the treatment of symptoms associated with osteoporosis. However, this use has largely been discontinued because the questionable efficacy of these agents for this indication does not justify the risk of serious adverse effects. /Anabolic steroids/
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. 140
Oxymetholone is indicated in the treatment of bone marrow failure anemias and deficient red cell production anemias. Acquired and congenital aplastic anemias, myelofibrosis, and hypoplastic anemias due to myelotoxic medication often respond to oxymetholone. Oxymetholone should not replace other supportive measures such as transfusions; correction of iron, folic acid, vitamin B12, or pyridoxine deficiency; antibacterial therapy; or the use of corticosteroids. /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. 140
For more Therapeutic Uses (Complete) data for OXYMETHOLONE (9 total), please visit the HSDB record page.
It has been proposed that prolonged use of such drugs /as oxymetholone/ may cause liver-cell damage or hyperplasia, thus predisposing to subsequent malignant transformation... On the other hand, underlying disease itself may have hepatic neoplasia as complication, which becomes apparent when survival is extended by drugs...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 137 (1977)
Use of anabolic steroids by athletes is not recommended. Objective evidence is conflicting and inconclusive as to whether these medications significantly increase athletic performance by increasing muscle strength. Weight gains reported by athletes are due in part to fluid retention, which is a potentially hazardous side effect of anabolic steroid therapy. The risk of other unwanted effects, such as testicular atrophy and suppression of spermatogenesis in males; menstrual disturbances and virilization, such as deepening of voice, development of acne, and unnatural growth of body hair in females; peliosis hepatis or other hepatotoxicity; and hepatic cancer outweigh and possible benefit received from anabolic steroids and make their use in athletes inappropriate. /Anabolic steroids/
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. 140
Leukemia has been observed in patients with aplastic anemia treated with oxymetholone, but the role of oxymetholone is unclear.
Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334
Contraindications: Hypersensitivity to anabolic steroids; male patients with prostate or breast carcinoma; carcinoma of the breast in females with hypercalcemia; nephrosis; the nephrotic phase of nephritis; pregnancy; to enhance physical appearance or athletic performance. /Anabolic steroids/
Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334
For more Drug Warnings (Complete) data for OXYMETHOLONE (18 total), please visit the HSDB record page.
Indicated in the treatment of anemias caused by deficient red cell production. Acquired aplastic anemia, congenital aplastic anemia, myelofibrosis and the hypoplastic anemias due to the administration of myelotoxic drugs often respond. Oxymetholone should not replace other supportive measures such as transfusion, correction of iron, folic acid, vitamin B12 or pyridoxine deficiency, antibacterial therapy and the appropriate use of corticosteroids.
FDA Label
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.)
Androgens
Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)
A - Alimentary tract and metabolism
A14 - Anabolic agents for systemic use
A14A - Anabolic steroids
A14AA - Androstan derivatives
A14AA05 - Oxymetholone
It is not known whether anabolic steroids are distributed into breast milk. /Anabolic steroids/
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. 141
One of the biotransformation routes of oxymetholone (17 beta-hydroxy-2-hydroxymethylene-17 alpha-methyl-5 alpha-androstan-3-one) in man leads to the formation of 17 beta-hydroxy-17 alpha-methyl-5 alpha-androstan-3-one (mestanolone). To demonstrate that this latter steroid may be formed by decarboxylation of an intermediate metabolite of oxymetholone bearing a 2-carboxylic group, we studied the urinary excretion of oxymetholone acidic metabolites. Five new acidic metabolites are reported here for the first time, among which four are unusual seco steroids resulting from the oxidative cleavage of the A-ring. The most abundant compound is 17 beta-hydroxy-17 alpha-methyl-2,3-seco-5 alpha-androstane-2,3-dioic acid 1, the cumulative excretion of which accounted for 1.52% of the dose. Three other seco diacids were produced in smaller amounts, namely 17 beta-hydroxy-17 alpha-methyl-2,3-seco-5 alpha-androstane-2,4- dicarboxylic acid 3, 17 beta-hydroxy-17 alpha-methyl-1,3-seco-5 alpha-androstane-1,3-dioic acid 4 and 17 beta-hydroxy-17 alpha-methyl-2,4-seco-5 alpha-androstane-2,4-dioic acid 5. The fifth acidic metabolite was identified as 3 alpha, 17 beta-dihydroxy-17 alpha-methyl-5 alpha-androstane-2 beta-carboxylic acid 2. The excretion in urine of these acidic metabolites suggests that the 2-hydroxymethylene group in oxymetholone is readily oxidized to yield the corresponding beta-keto acid which can be (1) decarboxylated to form mestanolone; (2) reduced at C-3 to give compound 2; and (3) further oxidized to afford the unexpected seco diacids 1, 3, 4 and 5.
PMID:1567786 Bi H et al; J Steroid Biochem Mol Biol 42 (2): 229-42 (1992)
About 5% of an oral dose 10 mg oxymetholone was recovered from urine as 2 unidentified metabolites...present in roughly equal proportions...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 134 (1977)
Oxymethalone is a 17 alpha-alkylated anabolic-androgenic steroid and a synthetic derivative of testosterone, whose anabolic effects are used to treat muscle wasting in HIV patients. The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Reverses catabolic processes and negative nitrogen balance by promoting protein anabolism and stimulating appetite if there is concurrently a proper intake of calories and proteins. /Anabolic steroids/
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. 141
Antianemic: Anemias due to bone marrow failure: Increases production and urinary excretion of erythropoietin. Anemias due to deficient red cell production : Stimulates erythropoietin production and may have a direct action on bone marrow. Anemias associated with renal disease: increases hemoglobin and red blood cell volume. /Anabolic steroids/
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. 141
Angioedema (hereditary) prophylactic: Increases serum concentration of Cl esterase inhibitor and, as a result, C2 and C4 concentrations . /Anabolic steroids/
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. 141
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