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    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
    Dihydrotestosterone
    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

    Dihydrotestosterone

    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 Weight 290.4 g/mol
    Molecular Formula C19H30O2
    XLogP33.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass290.224580195 g/mol
    Monoisotopic Mass290.224580195 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity459
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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

    Absorption

    Bioavailability is very low (0-2%) following oral administration.

    API Reference Price

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    07-Jul-2021
    01-May-2024
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