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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.


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Diosynth Bv

United Kingdom

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Diosynth Bv

United Kingdom
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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 8954

Submission : 1991-01-30

Status : Inactive

Type : II

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Nv Organon

U.S.A

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Nv Organon

U.S.A
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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 16907

Submission : 2003-10-15

Status : Inactive

Type : II

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Sigma F And D Div Ltd

U.S.A

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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 2596

Submission : 1976-01-16

Status : Inactive

Type : II

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Aspen API

Netherlands
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Dihydrotestosterone

About the Company : Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen...

Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen API works tirelessly to deliver top-quality APIs to clients worldwide. Aspen API has a portfolio of over 58 high-quality APIs, including high potency, oncology, peptides, narcotics, analgesics, botanical extractions, and biochemicals. Aspen API places a strong emphasis on sustainability. It employs eco-friendly technologies and solvents in its chemical processes, ensuring responsible and environmentally conscious manufacturing.
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Dihydrotestosterone

About the Company : Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable...

Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable operations, and innovation has driven their commitment to improving global healthcare access. With a state-of-the-art manufacturing facility inaugurated in 2004, Symbiotec has become a trusted provider in the industry. Their certifications including WHO-GMP, ISO, US FDA, and EU GMP showcase their dedication to quality and excellence. Over two decades, they've maintained their position through adaptability, efficiency, and competitive pricing.
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About the Company : Aasraw Biochemical Technology Co.,ltd was reorganized by a Shanghai based Biochemical Engineering Laboratory in 2008, which was built by 5 Chinese Ph. Doctors, who are majored at C...

Aasraw Biochemical Technology Co.,ltd was reorganized by a Shanghai based Biochemical Engineering Laboratory in 2008, which was built by 5 Chinese Ph. Doctors, who are majored at Chemical Engineering in University of Tulsa, Oklahoma, USA. The new born AASraw gained more investment and attracted more top genius guys in the biochemical industry. There are more advantaged equipment and instruments to be being adopted for analyzing, testing, Synthesis, etc., for example, DSC, GV, HPLC, UV, RV, etc. Till now, there are more than 20 key technology engineers. The fixed assets is more than USD30 million.
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[{"dataSource":"API Export","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1658255400,"product":"DIHYDROTESTOSTERONE (STANOLONE)","address":"385\/2, GRAM PIGDEMBER,","city":"INDORE, M.P.","supplier":"SYMBIOTEC PHARMALAB","supplierCountry":"INDIA","foreign_port":"BRUSSEL (BRUXELLES)","customer":"IPS INTERNATINAL PROJECT ","customerCountry":"BELGIUM","quantity":"60.00","actualQuantity":"60","unit":"KGS","unitRateFc":"717.7","totalValueFC":"42347.1","currency":"USD","unitRateINR":56121.533333333333,"date":"20-Jul-2022","totalValueINR":"3367292","totalValueInUsd":"42347.1","indian_port":"Indore-EPZ\/SEZ","hs_no":"29372900","bill_no":"4010360","productDescription":"API","marketType":"REGULATED MARKET","country":"BELGIUM","selfForZScoreResived":"Pharma Grade","supplierPort":"Indore-EPZ\/SEZ","supplierAddress":"385\/2, GRAM PIGDEMBER,, INDORE, M.P.","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1688668200,"product":"DIHYDROTESTOSTERONE (STANOLONE)","address":"385\/2, GRAM PIGDEMBER,","city":"INDORE, M.P.","supplier":"SYMBIOTEC PHARMALAB","supplierCountry":"INDIA","foreign_port":"BRUSSEL (BRUXELLES)","customer":"IPS INTERNATINAL PROJECT SUPPORT LTD.,","customerCountry":"BELGIUM","quantity":"90.00","actualQuantity":"90","unit":"KGS","unitRateFc":"988.9","totalValueFC":"88307.5","currency":"USD","unitRateINR":80643.888888888891,"date":"07-Jul-2023","totalValueINR":"7257950","totalValueInUsd":"88307.5","indian_port":"Indore-EPZ\/SEZ","hs_no":"29372900","bill_no":"4010129","productDescription":"API","marketType":"REGULATED MARKET","country":"BELGIUM","selfForZScoreResived":"Pharma Grade","supplierPort":"Indore-EPZ\/SEZ","supplierAddress":"385\/2, GRAM PIGDEMBER,, INDORE, M.P.","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1671733800,"product":"MESTEROLNE CHEMICAL NAME -METHYL-4,5-DIHYDROTESTOSTERONE 1-METHYL-DHT OR AS 1-METHYL 5-ANDROSTAN-17-OL-3-ONE","address":"12-Dec Shakti Nagar","city":"Delhi","supplier":"HUASUN PHARMACEUTICAL CO. LIMITED","supplierCountry":"CHINA","foreign_port":"NA","customer":"COOPER LAB","customerCountry":"INDIA","quantity":"6.37","actualQuantity":"6.37","unit":"KGS","unitRateFc":"2502","totalValueFC":"16158.7","currency":"USD","unitRateINR":"209039","date":"23-Dec-2022","totalValueINR":"1331578.13","totalValueInUsd":"16158.7","indian_port":"DELHI AIR","hs_no":"29371900","bill_no":"3868978","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"12-Dec Shakti Nagar"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1691001000,"product":"MESTEROLONE CHEMICAL NAME ?-METHYL-4,5?-DIHYDROTESTOSTERONE 1?-METHYL-DHT OR AS 1?-METHYL-5?-ANDROSTAN-17?-OL-3-ONE","address":"12\/12, , ,SHAKTI NAGAR,","city":"NEW DELHI","supplier":"HUBEI GOTO BIOPHARM CO LIMITED","supplierCountry":"CHINA","foreign_port":"NA","customer":"COOPER LAB","customerCountry":"INDIA","quantity":"6.37","actualQuantity":"6.37","unit":"KGS","unitRateFc":"1801.4","totalValueFC":"11557.6","currency":"USD","unitRateINR":"148794","date":"03-Aug-2023","totalValueINR":"957391.38","totalValueInUsd":"11557.6","indian_port":"DELHI AIR","hs_no":"29371900","bill_no":"0","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"12\/12, , ,SHAKTI NAGAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1714501800,"product":"OXYMETHOLONE CHEMICAL NAME (CI-406; NSC-26198;-HYDROXYMETHYLENE-17?-METHYL-4,5?-DIHYDROTESTOSTERONE; 2-HYDROXYMETHYLEN","address":"12\/12, SHAKTI NAGAR,","city":"DELHI","supplier":"WAHSUN PHARMACEUTICAL CO., LTD","supplierCountry":"CHINA","foreign_port":"HONG KONG","customer":"COOPER LAB","customerCountry":"INDIA","quantity":"7.65","actualQuantity":"7.65","unit":"KGS","unitRateFc":"550","totalValueFC":"4260.3","currency":"USD","unitRateINR":"46420","date":"01-May-2024","totalValueINR":"355113","totalValueInUsd":"4260.3","indian_port":"Delhi Air","hs_no":"29371900","bill_no":"3283058","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"2 ND FLOOR, NO. 1830, HUQING ROAD,QINGPU DISTRICT, SHANGHAISDNF CN","customerAddress":"12\/12, SHAKTI NAGAR,"}]
20-Jul-2022
01-May-2024
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