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Ethylestrenol

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2 FDF Dossiers, 2 FDA Orange Book

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2 FDA Orange Book

Synopsis

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Chemistry

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Also known as: Maxibolin, Orabolin, Ethylnandrol, Duraboral, Durabolin-o, Ethylestrenolum

Molecular Formula

C₂₀H₃₂O

Molecular Weight

288.5 g/mol

InChI Key

AOXRBFRFYPMWLR-XGXHKTLJSA-N

FDA UNII

ADC79EK5Q8

An anabolic steroid with some progestational activity and little androgenic effect.

1 2D Structure

Ethylestrenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-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/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1

2.1.3 InChI Key

AOXRBFRFYPMWLR-XGXHKTLJSA-N

2.1.4 Canonical SMILES

CCC1(CCC2C1(CCC3C2CCC4=CCCCC34)C)O

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

ADC79EK5Q8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ethyloestrenol

2. Maxibolin

2.3.2 Depositor-Supplied Synonyms

1. Maxibolin

2. Orabolin

3. Ethylnandrol

4. Duraboral

5. Durabolin-o

6. Ethylestrenolum

7. Etilestrenol

8. Ethyloestrenol

9. 965-90-2

10. Neodurabolin

11. Maxibalin

12. Orgabolin

13. Orgaboral

14. 17alpha-ethylestr-4-en-17beta-ol

15. 17alpha-ethyl-17beta-hydroxy-4-estrene

16. 19-nor-17alpha-pregn-4-en-17beta-ol

17. 17beta-hydroxy-17alpha-ethyl-19-nor-4-androstene

18. (17alpha)-19-norpregn-4-en-17-ol

19. Adc79ek5q8

20. Chebi:31578

21. Ethylnandrol (jan)

22. Nsc-37726

23. Ncgc00167514-01

24. Org-483

25. Ethyloestrenolum

26. Nsc 37726

27. Dsstox_cid_3024

28. Ethylnandrol [jan]

29. Dsstox_rid_76835

30. Dsstox_gsid_23024

31. (8r,9s,10r,13s,14s,17s)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ol

32. Etilestrenolo [dcit]

33. Etilestrenolo

34. (17beta)-17-ethylestr-4-en-17-ol

35. Etilestrenol [inn-spanish]

36. Ethylestrenolum [inn-latin]

37. Cas-965-90-2

38. Smr000238204

39. Hsdb 3327

40. 19-norpregn-4-en-17-ol, (17alpha)-

41. Einecs 213-523-6

42. Estr-4-en-17beta-ol, 17-ethyl-

43. Unii-adc79ek5q8

44. (17-alpha)-19-norpregn-4-en-17-ol

45. Ethylestrenol [usan:inn:ban]

46. Orabolin (tn)

47. 19-nor-17alpha-pregn-4-en-17-ol

48. 19-nor-17.alpha.-pregn-4-en-17.beta.-ol

49. 19-nor-17-alpha-pregn-4-en-17-ol

50. 19-norpregn-4-en-17-ol, (17-alpha)-

51. Ethylestrenol [mi]

52. Ethylestrenol [inn]

53. Ethylestrenol (usan/inn)

54. Ethylestrenol [hsdb]

55. Ethylestrenol [usan]

56. Ethylestrenol [vandf]

57. Mls000759411

58. Mls001424123

59. Ethylestrenol [mart.]

60. Schembl147908

61. Ethylestrenol [who-dd]

62. Gtpl6948

63. Chembl1200623

64. Dtxsid6023024

65. Hms2051p08

66. Ethylestrenol [orange Book]

67. Zinc4215863

68. Tox21_112512

69. Tox21_112512_1

70. Ccg-101014

71. Db01493

72. Nc00264

73. Ncgc00167514-02

74. D01414

75. Q764283

76. 19-norpregn-4-en-17-ol, (17.alpha.)

77. W-100138

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₂O
Molecular Weight	288.5 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	288.245315640 g/mol
Monoisotopic Mass	288.245315640 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	453
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 Therapeutic Uses

Anabolic Steroids

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

/Ethylestrenol/ has been used in for the promotion of growth in boys with short stature or delayed bone growth.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1554

4.2 Drug Warning

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 any 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

Hepatocellular carcinoma has been associated rarely with long-term, high-dose anabolic steroid therapy. /Anabolic Steroids/

Hepatic neoplasms have been associated rarely with long-term, high-dose anabolic steroid therapy. /Anabolic Steroids/

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

For more Drug Warnings (Complete) data for ETHYLESTRENOL (17 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 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.)

5.2 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AB - Estren derivatives

A14AB02 - Ethylestrenol

5.3 Absorption, Distribution and Excretion

The absorption, distribution, metabolism and excretion of [3H]ethylestrenol were studied in the rat. 2. Approximately one third of an intragastric dose was absorbed; 17% of the dose was excreted in urine and 83% in faeces within 10 days. 3. The dose is distributed throughout the rat, and kidney and liver were found to contain respectively 2.5-3 and 5-7 times the average specific activity of all other tissues. 4. Unchanged ethylestrenol was the only component detected in urine. Ethylestrenol was also found in faeces, along with two different dihydroxylated dihydro derivatives and one trihydroxylated dihydro derivative.

PMID:7233967 Stelle JW et al; Xenobiotica 11(2):103-15 (1981)

It is not known whether anabolic steroids are distributed into breast milk. /Anabolic Steroids/

5.4 Metabolism/Metabolites

Ethylestrenol incubated with a post-mitochondrial supernatant fraction of rat liver plus co-factors gives norethandrolone as the major metabolite. A second (minor) metabolite was tentatively identified as 17 alpha-ethyl-5 epsilon-estrane-3 epsilon,17 beta-diol. A pathway is suggested for the metabolism of ethylestrenol in the rat.

PMID:7233968 Steele JW et al; Xenobiotica. 1981 Feb;11(2):117-21.

Orabolin was oxidized at C-3 to form nilevar which in turn was metabolized in man by a ring reduction and side chain hydroxylation to form a 19-norpregnatriol. Identification of this metabolite, detection in urine is test for athletes suspected of drug misuse.

PMID:410996 Ward et al; J Steroid Biochem 8 (10): 1057-63 (1977)

5.5 Mechanism of Action

Anabolic steroids 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/

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