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08J2K08A3Y

08J2K08A3Y

Synopsis, Chemistry

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Also known as: Stanolone, Dihydrotestosterone, 521-18-6, Andractim, Anabolex, Androlone

Molecular Formula

C₁₉H₃₀O₂

Molecular Weight

290.4 g/mol

InChI Key

NVKAWKQGWWIWPM-ABEVXSGRSA-N

FDA UNII

08J2K08A3Y

A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.

1 2D Structure

08J2K08A3Y

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1

2.1.3 InChI Key

NVKAWKQGWWIWPM-ABEVXSGRSA-N

2.1.4 Canonical SMILES

CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C

2.1.5 Isomeric SMILES

C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C

2.2 Other Identifiers

2.2.1 UNII

08J2K08A3Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 17 Beta Hydroxy 5 Beta Androstan 3 One

2. 17 Beta-hydroxy-5 Beta-androstan-3-one

3. 17beta Hydroxy 5alpha Androstan 3 One

4. 17beta-hydroxy-5alpha-androstan-3-one

5. 5 Alpha Dht

6. 5 Alpha Dihydrotestosterone

7. 5 Alpha-dihydrotestosterone

8. 5 Beta Dihydrotestosterone

9. 5 Beta-dihydrotestosterone

10. 5-alpha Dihydrotestosterone

11. 5-alpha-dht

12. Anaprotin

13. Andractim

14. Beta-hydroxy-5 Beta-androstan-3-one, 17

15. Dihydroepitestosterone

16. Dihydrotestosterone

17. Dihydrotestosterone, 5-alpha

18. Gelovit

19. Stanolone

2.3.2 Depositor-Supplied Synonyms

1. Stanolone

2. Dihydrotestosterone

3. 521-18-6

4. Andractim

5. Anabolex

6. Androlone

7. Neodrol

8. 4-dihydrotestosterone

9. 5alpha-dihydrotestosterone

10. Anaboleen

11. Proteina

12. Stanaprol

13. Protona

14. Cristerona Mb

15. 17beta-hydroxy-5alpha-androstan-3-one

16. Dht

17. Androstanolona

18. Androstanolonum

19. 5alpha-androstan-17beta-ol-3-one

20. 5-alpha-dihydrotestosterone

21. Testosterone, Dihydro-

22. 4,5alpha-dihydrotestosterone

23. Stanorone

24. Dihydrotestosteron

25. 17beta-hydroxyandrostan-3-one

26. 5alpha-dht

27. 17beta-hydroxy-3-androstanone

28. Dihydrotestosterone (dht)

29. Nsc 10972

30. 5alpha,17beta-hydroxyandrostan-3-one

31. Androstanolone [inn]

32. Chebi:16330

33. 17-beta-hydroxy-5-alpha-androstan-3-one

34. 5alpha-dihydrotesosterone

35. 5alpha Dihydrotestosterone

36. Nsc-10972

37. Androstan-3-one, 17-hydroxy-, (5alpha,17beta)-

38. 5.alpha.-dihydrotestosterone

39. 5alpha-androstan-3-one, 17beta-hydroxy-

40. Chembl27769

41. (5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

42. 4,5.alpha.-dihydrotestosterone

43. (5alpha,17beta)-17-hydroxyandrostan-3-one

44. 17beta-hydroxy-androstan-3-one

45. 5-alpha-androstan-3-one, 17-beta-hydroxy-

46. 521-18-6 (free)

47. Androstan-3-one, 17-hydroxy-, (5a,17b)-

48. 17.beta.-hydroxy-3-androstanone

49. 08j2k08a3y

50. Androstanolone (inn)

51. 17beta-hydroxy-5alpha-androstane-3-one

52. 5.alpha.-androstan-17.beta.-ol-3-one

53. Ncgc00091013-01

54. Stanolon

55. 5.alpha.,17.beta.-hydroxyandrostan-3-one

56. Dsstox_cid_2364

57. Dsstox_rid_76558

58. Dsstox_gsid_22364

59. [3h]dht

60. 5alpha-dihydroxytestosterone

61. Androstan-17beta-ol-3-one

62. Androstanolonum [inn-latin]

63. (5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-10,13-dimethylhexadecahydro-3h-cyclopenta[a]phenanthren-3-one

64. Cas-521-18-6

65. Androstanolona [inn-spanish]

66. 4,5-alpha-dihydrotestosterone

67. 5-.alpha.-androstanolone

68. 5.alpha.-androstan-3-one, 17.beta.-hydroxy-

69. 17-hydroxyandrostan-3-one

70. [3h]dihydrotestosterone

71. [3h]-dihydrotestosterone

72. Einecs 208-307-3

73. 5alpha,17eta-hydroxyandrostan-3-one

74. Androstan-17.beta.-ol-3-one

75. 5-alpha-androstan-17-beta-ol-3-one

76. 17-beta-hydroxyandrostan-3-one

77. Androstan-3-one, 17-hydroxy-, (5.alpha.,17.beta.)-

78. Andrin

79. Unii-08j2k08a3y

80. (+)-androstan-17.beta.-ol-3-one

81. 1kdk

82. 2ama

83. (5-alpha,17-beta)-17-hydroxyandrostan-3-one

84. Andractim (tn)

85. (5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-10,13-dimethyltetradecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

86. 5-a-androstanolone

87. 5alpha-androstanolone

88. 5a-dihydrotestosterone

89. 17-.beta.-hydroxy-5-.alpha.-androstan-3-one

90. 5-alpha-androstanolone

91. 1d2s

92. 1t5z

93. 1t7r

94. Stanolone [mi]

95. (5.alpha.,17.beta.)-17-hydroxy-androstan-3-one

96. 4,5a-dihydrotestosterone

97. Androstan-17b-ol-3-one

98. Epitope Id:135868

99. 17-hydroxyandrostan-3-one, (5.alpha.,17.beta.)- #

100. Ec 208-307-3

101. 17b-hydroxy-3-androstanone

102. Bidd:pxr0075

103. Schembl15163

104. 17-hydroxy-androstan-3-one

105. Mls001304063

106. 5a-androstan-17b-ol-3-one

107. Bidd:er0136

108. 5.alpha.-dihydroxytestosterone

109. 5a-androstan-3-on-17b-ol

110. 5b-androstan-3-on-17b-ol

111. Androstanolone [mart.]

112. Gtpl2856

113. Gtpl3455

114. Androstanolone [who-dd]

115. Dtxsid9022364

116. Bdbm18161

117. 1t63

118. (+)-androstan-17beta-ol-3-one

119. Hms2272h05

120. Amy22298

121. Hy-a0120

122. Nsc10972

123. Zinc3814360

124. Tox21_111056

125. Tox21_200987

126. Tox21_303655

127. Bdbm50366473

128. Lmst02020042

129. S4757

130. Akos015894892

131. Ccg-267385

132. Cs-5096

133. Db02901

134. Gs-6587

135. Ncgc00091013-02

136. Ncgc00091013-03

137. Ncgc00257456-01

138. Ncgc00258540-01

139. 17beta-hydroxy-3-oxo-5alpha-androstanone

140. Ac-16144

141. Ac-33095

142. Smr000058342

143. Testosterone Impurity F [ep Impurity]

144. 5alpha-androstan-17beta-ol-3-one, >=97.5%

145. C03917

146. D07456

147. 521s186

148. Q411054

149. 17.beta.-hydroxy-5.alpha.-androstan-3-one

150. 17.beta.-hydroxy-5.alpha.-androstane-3-one

151. Androstanolone (5alpha-dihydrotestosterone; Stanolone)

152. 5alpha-androstan-17beta-ol-3-one, Purum, >=99.0% (tlc)

153. 5alpha-androstan-17beta-ol-3-one 100 Microg/ml In Acetonitrile

154. 5alpha-androstan-17beta-ol-3-one, Vetranal(tm), Analytical Standard

155. Androstanolone (5alpha-dihydrotestosterone; Stanolone) 1.0 Mg/ml In Acetonitrile

156. (1s,2s,7s,10r,11s,14s,15s)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadecan-5-one

157. (1s,2s,7s,10r,11s,14s,15s)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

158. (5s,8r,10s,13s,17s)-17-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

159. 17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16, 17-hexadecahydrocyclopenta[a]phenanthren-3-one

160. 5alpha-dihydrotestosterone (dht) Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₀O₂
Molecular Weight	290.4 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	290.224580195 g/mol
Monoisotopic Mass	290.224580195 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	459
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

4.2 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AA - Androstan derivatives

A14AA01 - Androstanolone

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03B - Androgens

G03BB - 5-androstanon (3) derivatives

G03BB02 - Androstanolone

4.3 Absorption, Distribution and Excretion