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Oxandrolone
Also known as: Anavar, Lonavar, Oxandrin, Vasorome, Provitar, 53-39-4
Molecular Formula
C19H30O3
Molecular Weight
306.4  g/mol
InChI Key
QSLJIVKCVHQPLV-PEMPUTJUSA-N
FDA UNII
7H6TM3CT4L

A synthetic hormone with anabolic and androgenic properties.
1 2D Structure

Oxandrolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
2.1.2 InChI
InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
2.1.3 InChI Key
QSLJIVKCVHQPLV-PEMPUTJUSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C)O)CCC4C3(COC(=O)C4)C
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(COC(=O)C4)C
2.2 Other Identifiers
2.2.1 UNII
7H6TM3CT4L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anavar

2. Oxandrin

3. Sc 11585

4. Sc-11585

5. Sc11585

2.3.2 Depositor-Supplied Synonyms

1. Anavar

2. Lonavar

3. Oxandrin

4. Vasorome

5. Provitar

6. 53-39-4

7. Ossandrolone [dcit]

8. Oxandrolonum

9. Oxandrolona

10. Oxandrolonum [inn-latin]

11. Oxandrolona [inn-spanish]

12. Protivar

13. Sc 11585

14. Sc-11585

15. Oxandrolone Ciii

16. (1s,3as,3br,5as,9as,9bs,11as)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one

17. (4as,4bs,6as,7s,9as,9br,11as)-7-hydroxy-4a,6a,7-trimethyltetradecahydroindeno[4,5-h]isochromen-2(1h)-one

18. 7h6tm3ct4l

19. Chebi:7820

20. Nsc-67068

21. Ossandrolone

22. Oxandrin (tn)

23. 8075 C. B.

24. Hsdb 3373

25. Einecs 200-172-9

26. Nsc 67068

27. Unii-7h6tm3ct4l

28. 8075 Cb

29. 17beta-hydroxy-17alpha-methyl-2-oxa-5alpha-androstan-3-one

30. Oxandrolone (jan/usp/inn)

31. 17beta-hydroxy-17-methyl-2-oxa-5alpha-androstan-3-one

32. Oxandrin;anavar

33. 2-oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5alpha,17beta)-

34. 17-beta-hydroxy-17-methyl-2-oxa-androstan-3-one

35. Dodecahydro-3-hydroxy-6-(hydroxy-methyl)-3,3a,6-trimethyl-1h-benz(e)indene-7-acetic Acid Delta-lactone

36. Oxandrolone [usan:usp:inn:ban:jan]

37. 2-oxa-5alpha-androstan-3-one, 17beta-hydroxy-17-methyl-

38. 8075 C.b.

39. Oxandrolone [mi]

40. Oxandrolone [inn]

41. Oxandrolone [jan]

42. Oxandrolone [hsdb]

43. Oxandrolone [usan]

44. Oxandrolone [vandf]

45. Oxandrolone [mart.]

46. Oxandrolone [who-dd]

47. 17.beta.-hydroxy-17-methyl-2-oxa-5.alpha.-androstan-3-one

48. Schembl148881

49. Gtpl7092

50. 2-oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5.alpha.,17.beta.)-

51. Chembl1200436

52. Dtxsid8023399

53. Oxandrolone, >=98% (hplc)

54. Oxandrolone [orange Book]

55. Oxandrolone Ciii [usp-rs]

56. 2-oxa-5-alpha-androstan-3-one, 17-beta-hydroxy-17-methyl-

57. Hms3712e22

58. Oxandrolone [usp Monograph]

59. Hy-b0707

60. Zinc3813047

61. 2-oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5-alpha,17-beta)-

62. Akos025401400

63. Ccg-220110

64. Db00621

65. Ac-14975

66. C07346

67. D00462

68. Ab01559948-01

69. 198o944

70. Q420859

71. Sr-01000872645

72. Sr-01000872645-1

73. W-105740

74. 17alpha-methyl-17beta-hydroxy-2-oxa-5alpha-androstan-3-one

75. (1s,2s,7s,10r,11s,14s,15s)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 306.4 g/mol
Molecular Formula C19H30O3
XLogP33.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass306.21949481 g/mol
Monoisotopic Mass306.21949481 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity503
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 4  
Drug NameOxandrin
PubMed HealthOxandrolone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelOxandrin oral tablets contain 2.5 mg or 10 mg of the anabolic steroid oxandrolone. Oxandrolone is 17-hydroxy-17-methyl-2-oxa-5-androstan-3-one with the following structural formula:Inactive ingredients include cornstarch, lactose, magnesium s...
Active IngredientOxandrolone
Dosage FormTablet
RouteOral
Strength2.5mg; 10mg
Market StatusPrescription
CompanyCrealta Pharms

2 of 4  
Drug NameOxandrolone
PubMed HealthOxandrolone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelOxandrolone Tablets, USP, oral tablets, contain 10 mg of the anabolic steroid oxandrolone. Oxandrolone is 17-hydroxy-17-methyl-2-oxa-5-androstan-3-one with the following structural formula:Inactive ingredients include anhydrous lactose, hyprome...
Active IngredientOxandrolone
Dosage FormTablet
RouteOral
Strength2.5mg; 10mg
Market StatusPrescription
CompanyUpsher Smith; Par Pharm

3 of 4  
Drug NameOxandrin
PubMed HealthOxandrolone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelOxandrin oral tablets contain 2.5 mg or 10 mg of the anabolic steroid oxandrolone. Oxandrolone is 17-hydroxy-17-methyl-2-oxa-5-androstan-3-one with the following structural formula:Inactive ingredients include cornstarch, lactose, magnesium s...
Active IngredientOxandrolone
Dosage FormTablet
RouteOral
Strength2.5mg; 10mg
Market StatusPrescription
CompanyCrealta Pharms

4 of 4  
Drug NameOxandrolone
PubMed HealthOxandrolone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelOxandrolone Tablets, USP, oral tablets, contain 10 mg of the anabolic steroid oxandrolone. Oxandrolone is 17-hydroxy-17-methyl-2-oxa-5-androstan-3-one with the following structural formula:Inactive ingredients include anhydrous lactose, hyprome...
Active IngredientOxandrolone
Dosage FormTablet
RouteOral
Strength2.5mg; 10mg
Market StatusPrescription
CompanyUpsher Smith; Par Pharm

4.2 Therapeutic Uses

Anabolic Steroids

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


Oxandrolone ... /is/ indicated in conditions such as chronic infections, extensive surgery, (corticosteroid-induced myopathy, decubitus ulcers, burns, /NOT included in US product labeling/) or severe trauma, which require reversal of catabolic processes or protein-sparing effects. /This agent is/ ... adjunct to, and not replacement for, conventional treatment of these disorders. /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


Oxandrolone is used in the treatment of the short stature that accompanies Turner's syndrome (gonadal dysgenesis in females). Although the therapy is controversial, recent experimental reports seem to indicate that oxandrolone may be as effective as growth hormone and that oxandrolone may increase the efficacy of growth hormone therapy. /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. 140


Anabolic steroids may be used in children as an adjunct in the treatment of growth failure caused by pituitary growth hormone (GH) deficiency (pituitary dwarfism) or if the response to human growth hormone administration is inadequate. /Anabolic steroids; 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. 140


For more Therapeutic Uses (Complete) data for OXANDROLONE (6 total), please visit the HSDB record page.


4.3 Drug Warning

Peliosis hepatis, a condition in which liver and sometimes splenic tissue is replaced with blood-filed cysts, has occurred in patients receiving androgenic anabolic steroids. These cysts are sometimes present with minimal hepatic dysfunction and have been associated with liver failure. They are often not recognized until life-threatening liver failure or intro-abdominal hemorrhage develops. Withdrawal of drug usually results in complete disappearance of lesions. /Anabolic steroids/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334


Liver cell tumors: Most often these tumors are benign and androgen-dependent, but fatal malignant tumors have occurred. Withdrawal of drug often results in regression or cessation of tumor progression. However, hepatic tumors associated with androgens or anabolic steroids are much more vascular than other hepatic tumors and may be silent until life-threatening intra-abdominal hemorhage develops. /Anabolic steroids/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 324


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


Anabolic steroids are not recommended for use during pregnancy, since studies in animals have shown that anabolic steroids cause masculinization of the fetus. Risk-benefit must be carefully considered. /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


For more Drug Warnings (Complete) data for OXANDROLONE (22 total), please visit the HSDB record page.


4.4 Drug Indication

Use to promote weight gain after weight loss following extensive surgery.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Oxandrolone is an anabolic steroids indicated as adjunctive therapy to promote weight gain after weight loss following extensive surgery, chronic infections, or severe trauma, and in some patients who without definite pathophysiologic reasons fail to gain or to maintain normal weight, to offset the protein catabolism associated with prolonged administration of corticosteroids, and for the relief of the bone pain frequently accompanying osteoporosis. Anabolic steroids are synthetic derivatives of testosterone.


5.2 MeSH Pharmacological Classification

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.)


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 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AA - Androstan derivatives

A14AA08 - Oxandrolone


5.4 Absorption, Distribution and Excretion

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


5.5 Metabolism/Metabolites

Renal


The metabolism of 17 alpha-methyl-17 beta-hydroxy-2-oxa-5 alpha-androstan-3-one (oxandrolone) in man has been investigated by gas chromatography/mass spectrometry. After oral administration of a 10 mg dose to man, five metabolites were detected in the free fraction of the urinary samples. Oxandrolone, the major compound excreted in urine, was detected within 72 hr after administration. During this period 35.8 and 8.4% of the administered dose was excreted as unchanged oxandrolone and 17-epioxandrolone, respectively. In addition, minute amounts of 16 alpha- and 16 beta-hydroxyoxandrolone and a delta-hydroxy acid resulting from the hydrolysis of the lactone group of oxandrolone were detected in the urine samples 8-60 hr after administration.

PMID:2765703 Masse R et al; Biomed Environ Mass Spectrom 18 (6): 429-38 (1989)


5.6 Biological Half-Life

0.55 hours (1st phage), 9 hours (2nd phase)


Biphasic: 1st phase - 0.55 hours. 2nd phase - 9 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. 141


5.7 Mechanism of Action

Oxandrolones interact with androgen receptors in target tissues.


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


There was abs decrease in total serum cholesterol and redistribution of cholesterol, such that post-treatment low-density lipoprotein carried less cholesterol and high-density lipoprotein more cholesterol on percentage basis than found in pre-treatment values with oxandrolone.

FREEMAN MW ET AL; J GERONTOL 35(1) 31 (1980)


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