Metribolone

Synopsis, Chemistry

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Also known as: Metribolone, 965-93-5, R1881, 17alpha-methyltrienolone, Metribolona, Metribolonum

Molecular Formula

C₁₉H₂₄O₂

Molecular Weight

284.4 g/mol

InChI Key

CCCIJQPRIXGQOE-XWSJACJDSA-N

FDA UNII

2C323EGI97

A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.

1 2D Structure

Metribolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1

2.1.3 InChI Key

CCCIJQPRIXGQOE-XWSJACJDSA-N

2.1.4 Canonical SMILES

CC1(CCC2C1(C=CC3=C4CCC(=O)C=C4CCC23)C)O

2.1.5 Isomeric SMILES

C[C@@]1(CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C)O

2.2 Other Identifiers

2.2.1 UNII

2C323EGI97

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 17 Beta-hydroxy-17 Alpha-methylestra-4,9,11-trien-3-one

2. Metribolone

3. R 1881

4. R-1881

5. R1881

6. Ru 1881

7. Ru-1881

8. Ru1881

2.3.2 Depositor-Supplied Synonyms

1. Metribolone

2. 965-93-5

3. R1881

4. 17alpha-methyltrienolone

5. Metribolona

6. Metribolonum

7. R 1881

8. Ru 1881

9. 17-beta-hydroxy-17-methylestra-4,9,11-trien-3-one

10. R-1881

11. (17beta)-17-hydroxy-17-methylestra-4,9,11-trien-3-one

12. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one

13. Nsc-92858

14. R1881 (synthetic Androgen)

15. Chebi:379896

16. 2c323egi97

17. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17b)-

18. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)-

19. 17-methyloestra-4,9,11-trien-3-one,17beta-ol

20. (8s,13s,14s,17s)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,13,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-3-one

21. (8s,13s,14s,17s)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

22. Ru-1881

23. [3h]methyltrienolone

24. Mls002695156

25. Metribolone [inn:dcf]

26. Metribolonum [inn-latin]

27. Metribolona [inn-spanish]

28. Unii-2c323egi97

29. Methyl Trienolone

30. 1xow

31. Nsc 92858

32. 1e3g

33. 2ao6

34. [3h]r1881

35. Metribolone [inn]

36. [3h]-r1881

37. 17.alpha.-methyltrienolone

38. Metribolone [mart.]

39. 17-.alpha.-methyltrienolone

40. Methyltrienolone [mi]

41. Metribolone [who-dd]

42. Schembl114862

43. Chembl166444

44. Gtpl2857

45. Gtpl3457

46. Dtxsid8034162

47. Nsc92858

48. Zinc3814420

49. Bdbm50367916

50. Akos015840270

51. Db02998

52. Ac-32028

53. R1881, >=98% (hplc)

54. 965m935

55. A845615

56. Q3333717

57. 17-.beta.-hydroxy-17-methylestra-4,11-trien-3-one

58. 17alpha-methyl-3-oxo-4,9,11-estratrien-17beta-ol

59. 17alpha-methyl-4,9,11,estratrien-17beta-ol-3-one

60. 3-oxo-17beta-hydroxy-17-methylestra-4,9,11-triene

61. 17alpha-methyl-17beta-hydroxyestr-4,9,11-trien-3-one

62. 17alpha-methyl-17beta-hydroxyestra-4,9,11-trien-3-one

63. Estra-4,11-trien-3-one, 17.beta.-hydroxy-17-methyl-

64. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl-

65. 17alpha-methyl-17beta-hydroxy-estra-4,9,11-trien-3-one

66. 3-oxo-17beta-hydroxy-17alpha-methylestra-4,9,11-triene

67. (17beta)-17-hydroxy-17-methyl-estra-4,9,11-triene-3-one

68. 17-beta-hydroxy-17-methylestra-4,9,11-trien-3-one (9ci)

69. 17.beta.-hydroxy-17-methylestra-4,9,11-trien-3-one

70. 17alpha-methyl-17beta-hydroxyestra-4,9(10),11-trien-3-one

71. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (8ci)

72. 17-beta-hydroxy-17-methyl-19-norandrosta-4,9,11-triene-3-one

73. Estra-4,11-trien-3-one, 17-hydroxy-17-methyl-, (17.beta.)-

74. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (7ci,8ci)

75. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)- (9ci)

76. Methyltrienolone; 17beta-hydroxy-17methyl-19norandrosta-4,9,11-trien-3-one; R1881

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₄O₂
Molecular Weight	284.4 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	284.177630004 g/mol
Monoisotopic Mass	284.177630004 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	609
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1