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Chemistry

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Also known as: Dromostanolone propionate, 521-12-0, Permastril, Emdisterone, Masterid, Masteron
Molecular Formula
C23H36O3
Molecular Weight
360.5  g/mol
InChI Key
NOTIQUSPUUHHEH-UXOVVSIBSA-N
FDA UNII
X20UZ57G4O

Dromostanolone Propionate
Dromostanolone Propionate is the propionate salt form of dromostanolone, a synthetic anabolic steroid related to dihydrotestosterone that has antiestrogenic effects. Dromostanolone inhibits the growth of estrogen receptor-presenting breast cancers; its virilizing effects limit its clinical usefulness. (NCI)
1 2D Structure

Dromostanolone Propionate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2R,5S,8R,9S,10S,13S,14S,17S)-2,10,13-trimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] propanoate
2.1.2 InChI
InChI=1S/C23H36O3/c1-5-21(25)26-20-9-8-17-16-7-6-15-12-19(24)14(2)13-23(15,4)18(16)10-11-22(17,20)3/h14-18,20H,5-13H2,1-4H3/t14-,15+,16+,17+,18+,20+,22+,23+/m1/s1
2.1.3 InChI Key
NOTIQUSPUUHHEH-UXOVVSIBSA-N
2.1.4 Canonical SMILES
CCC(=O)OC1CCC2C1(CCC3C2CCC4C3(CC(C(=O)C4)C)C)C
2.1.5 Isomeric SMILES
CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H](C(=O)C4)C)C)C
2.2 Other Identifiers
2.2.1 UNII
X20UZ57G4O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Alpha-methyldihydrotestosterone Propionate

2. Drolban

3. Dromostanolone Propionate

4. Masteril

5. Masterone

6. Nsc 12198

7. Nsc-12198

2.3.2 Depositor-Supplied Synonyms

1. Dromostanolone Propionate

2. 521-12-0

3. Permastril

4. Emdisterone

5. Masterid

6. Masteron

7. Blackburn Compound

8. Drolban

9. 2mdtp

10. 2m-dhtp

11. Masteril

12. Masterone

13. Medrotestron Propionate

14. Medrotestrone Propanoate

15. Medrotestrone Propionate

16. Mdht

17. Dromostanolone Proprionate

18. Lilly 32379

19. Re 346

20. Nsc-1298

21. Dromostanolone 17-propionate

22. Rs 1567

23. 2alpha-methyl-4,5-dihydrotestosterone Propionate

24. Testosterone, 4,5alpha-dihydro-2alpha-methyl-, Propionate

25. Nsc-12198

26. 17beta-hydroxy-2alpha-methyl-5alpha-androstan-3-one Propionate

27. X20uz57g4o

28. Chebi:31523

29. Dromostanolone Propionate [usan]

30. [(2r,5s,8r,9s,10s,13s,14s,17s)-2,10,13-trimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] Propanoate

31. Androstan-3-one, 2-methyl-17-(1-oxopropoxy)-, (2a,5a,17b)-

32. 2.alpha.-methyldihydrotestosterone Propionate

33. 17.beta.-hydroxy-2.alpha.-methyl-5.alpha.-androstan-3-one Propionate

34. 2.alpha.-methyl-4,5-dihydrotestosterone Propionate

35. Drostanolone Propionate (jan)

36. 2alpha-methyl-3-oxo-5alpha-androstan-17beta-yl Propanoate

37. Dromostanolone Propionate (usan)

38. Nomasteron

39. Drostanolone Propionate [jan]

40. (2r,5s,8r,9s,10s,13s,14s,17s)-2,10,13-trimethyl-3-oxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl Propionate

41. Drolban (tn)

42. Unii-x20uz57g4o

43. Masteron (tn)

44. Einecs 208-303-1

45. Dromostanolone Propionate [usan:usp]

46. Brn 3161958

47. Ai3-52810

48. Schembl3173

49. Androstan-3-one, 2-methyl-17-(1-oxopropoxy)-

50. 4-08-00-00654 (beilstein Handbook Reference)

51. 17b-hydroxy-2a-methyl-5a-androstan-3-one Propionate

52. Gtpl6947

53. Chembl1201048

54. Dtxsid1022972

55. Androstan-3-one, 2-methyl-17-(1-oxopropoxy)-, (2.alpha.,5.alpha.,17.beta.)-

56. (2alpha,5alpha,17beta)-2-methyl-3-oxoandrostan-17-yl Propanoate

57. Nsc12198

58. Zinc4213057

59. Mfcd01669961

60. S4794

61. Dromostanolone Propionate [mi]

62. Akos015895157

63. Ccg-268166

64. Db14655

65. Drostanolone Propionate [mart.]

66. Ds-3972

67. Drostanolone Propionate [who-dd]

68. Ncgc00507798-01

69. Hy-107344

70. Cs-0028187

71. C15917

72. D01534

73. Dromostanolone Propionate [orange Book]

74. 521d120

75. A828929

76. Q5308606

77. W-105852

78. Drostanolone Propionate 100 Microg/ml In Acetonitrile

79. Testosterone,5.alpha.-dihydro-2.alpha.-methyl-, Propionate

80. Testosterone, 4,5.alpha.-dihydro-2.alpha.-methyl-, Propionate

81. Androstan-3-one,2-methyl-17-(1-oxopropoxy)-,(2

82. A,5

83. A,17

84. A)-

85. 5-alpha-androstan-3-one, 17-beta-hydroxy-2-alpha-methyl-, Propionate

86. 5.alpha.-androstan-3-one, 17.beta.-hydroxy-2.alpha.-methyl-, Propionate

87. Androstan-3-one, 2-methyl-17-(1-oxopropoxy)-, (2alpha,5alpha,17beta)-

88. 2-methyl-3-oxoandrostan-17-yl Propionate, (2.alpha.,5.alpha.,17.beta.)- #

89. Androstan-3-one, 2-methyl-17-(1-oxopropoxy)-, (2.alpha.,5.alpha.,17.beta

90. [(2r,5s,8r,9s,10s,13s,14s,17s)-2,10,13-trimethyl-3-oxidanylidene-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] Propanoate

91. Propanoic Acid [(2r,5s,8r,9s,10s,13s,14s,17s)-2,10,13-trimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] Ester

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 360.5 g/mol
Molecular Formula C23H36O3
XLogP35.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass360.26644501 g/mol
Monoisotopic Mass360.26644501 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count26
Formal Charge0
Complexity598
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For use 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

Dromostanolone is a synthetic androgen, or male hormone, similar to testosterone. Dromostanolone 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 Absorption, Distribution and Excretion

Absorption

Well absorbed following parenteral administration.


5.3 Mechanism of Action

Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.


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