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2D Structure
Also known as: 17-methyltestosterone, Testred, Metandren, Android, Virilon, 58-18-4
Molecular Formula
C20H30O2
Molecular Weight
302.5  g/mol
InChI Key
GCKMFJBGXUYNAG-HLXURNFRSA-N
FDA UNII
V9EFU16ZIF

A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).
Methyltestosterone is an Androgen. The mechanism of action of methyltestosterone is as an Androgen Receptor Agonist.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
2.1.3 InChI Key
GCKMFJBGXUYNAG-HLXURNFRSA-N
2.1.4 Canonical SMILES
CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C)O)C
2.1.5 Isomeric SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C
2.2 Other Identifiers
2.2.1 UNII
V9EFU16ZIF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Alpha Methyltestosterone

2. 17 Beta Hydroxy 17 Methyl 4 Androsten 3 One

3. 17 Beta Methyltestosterone

4. 17 Beta-hydroxy-17-methyl-4-androsten-3-one

5. 17 Beta-methyltestosterone

6. 17 Epimethyltestosterone

7. 17-alpha-methyltestosterone

8. 17-epimethyltestosterone

9. 17alpha Methyl Testosterone

10. 17alpha Methyltestosterone

11. 17alpha-methyl-testosterone

12. 17alpha-methyltestosterone

13. 17beta Hydroxy 17 Methyl 4 Androsten 3 One

14. 17beta Methyltestosterone

15. 17beta-hydroxy-17-methyl-4-androsten-3-one

16. 17beta-methyltestosterone

17. Android (methyltestoterone)

18. Android 10

19. Android 25

20. Android 5

21. Android-10

22. Android-25

23. Android-5

24. Mesteron

25. Mesterone

26. Metandren

27. Methitest

28. Oreton

29. Testoviron

30. Testred

31. Virilon

2.3.2 Depositor-Supplied Synonyms

1. 17-methyltestosterone

2. Testred

3. Metandren

4. Android

5. Virilon

6. 58-18-4

7. Androsan

8. Androsten

9. Mesterone

10. 17alpha-methyltestosterone

11. Malestrone

12. Mastestona

13. Synandrets

14. Synandrotabs

15. Testhormone

16. Andrometh

17. Anertan

18. Dumogran

19. Homandren

20. Hormale

21. Malogen

22. Masenone

23. Metestone

24. Metrone

25. Nabolin

26. Oraviron

27. Steronyl

28. Syndren

29. Testora

30. Oreton Methyl

31. Glosso-sterandryl

32. Oreton-m

33. M.t.mucorettes

34. Neo-hombreol-m

35. Nu-man

36. Android 5

37. Android 10

38. Android 25

39. Methitest

40. Nsc-9701

41. Orchisterone-m

42. Testovis Depot

43. Homandren, Tablets

44. Metiltestosterona

45. Methyltestosteronum

46. 17beta-hydroxy-17-methylandrost-4-en-3-one

47. Ru 24400

48. 17-methyltestosteron

49. Cdb 110

50. Anertan, Tablets

51. 17-hydroxy-17-methyl-3-keto-androstene-4

52. 17alpha-methyl-3-oxo-4-androsten-17beta-ol

53. 17-beta-hydroxy-17-methylandrost-4-en-3-one

54. 17.alpha.-methyltestosterone

55. 4-androstene-17alpha-methyl-17beta-ol-3-one

56. Methyltestosterone Ciii

57. L 589.372

58. 17

59. A-methyltestosterone

60. Methyl Testosterone

61. U 2842

62. V9efu16zif

63. 17alpha-methyl-delta-androsten-17beta-ol-3-one

64. Nsc-139965

65. Chebi:27436

66. Oreton M

67. Androsan, Tablets

68. Cdb-110

69. Component Of Estan

70. (17beta)-17-hydroxy-17-methylandrost-4-en-3-one

71. Neo-hombreol [m]

72. Neo-homobreol (m)

73. Neo-homobreol [m]

74. Component Of Gynetone

75. (8r,9s,10r,13s,14s,17s)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one

76. Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17b)-

77. Ncgc00091009-03

78. Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-

79. Component Of Tylosterone

80. Estratest

81. Ru-24400

82. Glosso Sterandryl

83. Testosterone, 17-methyl-

84. U-2842

85. Dsstox_cid_13664

86. Dsstox_rid_79089

87. Anertan (tablets)

88. Dsstox_gsid_33664

89. Homandren (van)

90. Testovis (tablet)

91. 17.alpha.-methyl-3-oxo-4-androsten-17.beta.-ol

92. Androsan (tablets)

93. Androsan (van)

94. Testoviron (van)

95. Anertan (van)

96. 4-androstene-17.alpha.-methyl-17.beta.-ol-3-one

97. Androst-4-en-3-one, 17.beta.-hydroxy-17-methyl-

98. L-589372

99. Testoviron (tablet)

100. L-589.372

101. Oretron

102. Metiltestosterone

103. Estan (salt/mix)

104. Metiltestosterone [dcit]

105. 17-alpha-methyltestosterone

106. Cas-58-18-4

107. Estratest (salt/mix)

108. Smr000058528

109. Android (tn)

110. Ccris 3723

111. Methyltestosteronum [inn-latin]

112. Metiltestosterona [inn-spanish]

113. Hsdb 3365

114. Wln: L E5 B666 Ov Mutj A E Fq F -b&aef

115. Einecs 200-366-3

116. Unii-v9efu16zif

117. Nsc 139965

118. Brn 2057425

119. Component Of Gynetone (salt/mix)

120. Premarin With Methyltestosterone

121. 4-androstene-17-alpha-methyl-17-beta-ol-3-one

122. Ncgc00091009-04

123. Ncgc00091009-05

124. Androst-4-en-3-one, 17beta-hydroxy-17-methyl-

125. Testred (tn)

126. (17-beta)-17-hydroxy-17-methylandrost-4-en-3-one

127. Premarin With Methyltestosterone (salt/mix)

128. 17(alpha)-methyl-delta4-androsten-17(beta)-ol-3-one

129. 17-hydroxy-17-methylandrost-4-en-3-one #

130. 17a-methyltestosterone

131. Methyltestosterone [usp:inn:ban:jan]

132. 17-.beta.-hydroxy-17-methylandrost-4-en-3-one

133. Androst-4-en-3-on-17.beta.-ol, 17.alpha.-methyl

134. Androst-4-ene-17.alpha.-methyl-17.beta.-ol-3-one

135. 17.beta.-hydroxy-17.alpha.-methylandrost-4-en-3-one

136. 17.alpha.-methyl-.delta.4-androsten-17.beta.-ol-3-one

137. Chembl1395

138. Schembl18657

139. 4-08-00-01010 (beilstein Handbook Reference)

140. Androst-4-en-3-one, 17-beta-hydroxy-17-methyl-

141. Mls000759474

142. Mls001424040

143. Mls002174282

144. Gtpl6945

145. Methyltestosterone [inn]

146. Methyltestosterone [jan]

147. Dtxsid1033664

148. Methyltestosterone [hsdb]

149. .alpha.-methyltestosterone

150. Methyltestosterone [vandf]

151. Nsc9701

152. 17-mt

153. Hms2051a14

154. Hms2272a06

155. Methyltestosterone [mart.]

156. Methyltestosterone [usp-rs]

157. Methyltestosterone [who-dd]

158. Methyltestosterone [who-ip]

159. 17-methyltestosterone [mi]

160. Hy-a0121

161. Zinc3814422

162. Tox21_113161

163. Tox21_113162

164. Tox21_400058

165. Bdbm50410531

166. Lmst02020029

167. Methyltestosterone (jp17/usp/inn)

168. Nsc139965

169. Akos015917317

170. Tox21_113162_1

171. Ccg-100871

172. Cs-5099

173. Db06710

174. Gs-6594

175. Nc00121

176. Methyltestosterone [orange Book]

177. Methyltestosterone [ep Monograph]

178. Ncgc00091009-01

179. Ncgc00091009-06

180. Ncgc00091009-07

181. Oxandrolone Impurity, Methyltestosterone-

182. (8r,9s,10r,13s,14s,17s)-17-hydroxy-10,13,17-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3h-cyclopenta[a]phenanthren-3-one

183. Methyltestosterone [usp Monograph]

184. Methyltestosteronum [who-ip Latin]

185. Smr001261452

186. M0435

187. 17alpha-methyltestosterone, >=97.0% (hplc)

188. C07198

189. D00408

190. Methyltestosterone (17alpha-methyltestosterone)

191. Ab00443683-06

192. Ab00443683-09

193. 17alpha-methyl-delta4-androsten-17beta-ol-3-one

194. 17alpha-methyltestosterone, Solid (photosensitive)

195. Q421768

196. 17alpha-methyl-delta(4)-androsten-17beta-ol-3-one

197. 17-alpha-methyltestosterone 100 Microg/ml In Methanol

198. 17.beta.-hydroxy-17-methylandrost-4-en-3-one

199. 17(alpha)-methyl-delta(4)-androsten-17(beta)-ol-3-one

200. 17-alpha-methyltestosterone 100 Microg/ml In Acetonitrile

201. 17alpha-methyltestosterone, Vetranal(tm), Analytical Standard

202. Oxandrolone Impurity, Methyltestosterone- [usp Impurity]

203. Methyltestosterone, European Pharmacopoeia (ep) Reference Standard

204. Methyltestosterone (17alpha-methyltestosterone) 1.0 Mg/ml In Acetonitrile

205. Methyltestosterone, United States Pharmacopeia (usp) Reference Standard

206. Methyltestosterone For System Suitability, European Pharmacopoeia (ep) Reference Standard

207. (1s,2r,10r,11s,14s,15s)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

208. (8r,10r,13s,17s)-17-hydroxy-10,13,17-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

209. 17alpha-methyltestosterone Solution, 1.0 Mg/ml In 1,2-dimethoxyethane, Ampule Of 1 Ml, Certified Reference Material

210. Methyltestosterone Aka ''(8r,9s,10r,13s,14s,17s)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 302.5 g/mol
Molecular Formula C20H30O2
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass302.224580195 g/mol
Monoisotopic Mass302.224580195 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count22
Formal Charge0
Complexity550
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameAndroid 10
PubMed HealthMethyltestosterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelThe androgens are steroids that develop and maintain primary and secondary male sex characteristics.Androgens are derivatives of cyclopentanoperhydrophenanthrene. Endogenous androgens are C-19 steroids with a side chain at C-17, and with two angular...
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength10mg
Market StatusPrescription
CompanyValeant Pharm Intl

2 of 8  
Drug NameAndroid 25
PubMed HealthMethyltestosterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelThe androgens are steroids that develop and maintain primary and secondary male sex characteristics.Androgens are derivatives of cyclopentanoperhydrophenanthrene. Endogenous androgens are C-19 steroids with a side chain at C-17, and with two angular...
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyValeant Pharm Intl

3 of 8  
Drug NameMethyltestosterone
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength25mg; 10mg
Market StatusPrescription
CompanyImpax Labs

4 of 8  
Drug NameTestred
Active IngredientMethyltestosterone
Dosage FormCapsule
RouteOral
Strength10mg
Market StatusPrescription
CompanyValeant Pharm Intl

5 of 8  
Drug NameAndroid 10
PubMed HealthMethyltestosterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelThe androgens are steroids that develop and maintain primary and secondary male sex characteristics.Androgens are derivatives of cyclopentanoperhydrophenanthrene. Endogenous androgens are C-19 steroids with a side chain at C-17, and with two angular...
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength10mg
Market StatusPrescription
CompanyValeant Pharm Intl

6 of 8  
Drug NameAndroid 25
PubMed HealthMethyltestosterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelThe androgens are steroids that develop and maintain primary and secondary male sex characteristics.Androgens are derivatives of cyclopentanoperhydrophenanthrene. Endogenous androgens are C-19 steroids with a side chain at C-17, and with two angular...
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyValeant Pharm Intl

7 of 8  
Drug NameMethyltestosterone
Active IngredientMethyltestosterone
Dosage FormTablet
RouteOral
Strength25mg; 10mg
Market StatusPrescription
CompanyImpax Labs

8 of 8  
Drug NameTestred
Active IngredientMethyltestosterone
Dosage FormCapsule
RouteOral
Strength10mg
Market StatusPrescription
CompanyValeant Pharm Intl

4.2 Therapeutic Uses

Anabolic Steroids; Androgens, Synthetic; Antineoplastic Agents, Hormonal

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Androgens are primarily indicated in males as replacement therapy when congenital or acquired endogenous androgen absence or deficiency is associated with primary hypogonadal or secondary hypogonadism. Primary hypogonadism includes conditions such as testicular failure due to cryptorchidism, bilateral torsion, orchitis, or vanishing testis syndrome; inborn errors in testosterone biosynthesis; or bilateral orchidectomy. Hypogonadotropic hypogonadism (secondary hypogonadism) conditions include gonadotropin releasing hormone (GnRH) deficiency; or pituitary hypothalamic injury as a result of surgery, tumors, trauma, or radiation and are the most common forms of hypogonadism seen in older adults. Dosage adjustment is needed to accommodate individual clinical requirements for such life changes as induction of puberty, development of secondary sexual characteristics, impotence due to testicular failure, or infertility due to oligospermia.. /Androgens; Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 150


A 6 month or shorter course of an androgen is indicated for induction of puberty in patients with familial delayed puberty, a condition characterized by spontaneous, nonpathologic, late-onset puberty, if the patient does not respond to psychological treatment. /Androgens; Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


Androgens are used in the treatment of constitutional delay in growth. However, they are not longer considered the treatment of choice for most patients. /Androgens; NOT included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


For more Therapeutic Uses (Complete) data for 17-METHYLTESTOSTERONE (6 total), please visit the HSDB record page.


4.3 Drug Warning

Cholestatic hepatitis and jaundice and abnormal liver function test results may occur in patients receiving 17-alpha-alkylandrogens such as methyltestosterone. These adverse hepatic effects may occur at relatively low doses of the drug. Drug-induced jaundice usually is reversible following discontinuance of the drug. Methyltestosterone should be discontinued if cholestatic jaundice or hepatitis occurs, or if liver function test results become abnormal during therapy with the drug, and the etiology of these disorders should be determined. Peliosis of the liver and hepatic neoplasms, including hepatocellular carcinoma, have been reported rarely in patients receiving long-term administration of androgenic anabolic steroids. Peliosis of the liver can be a life-threatening or fatal complication of androgen therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2948


It is not known whether methyltestosterone is distributed into milk. Because of the potential for serious adverse reactions to androgens in nursing infants, a decision should be made whether to discontinue nursing or to not use methyltestosterone, taking into account the importance of the drug to the woman.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2948


Methyltestosterone is contraindicated in males with carcinoma of the breast or known or suspected carcinoma of the prostate. Some manufacturers state that the drug also is contraindicated in patients with cardiac, renal, or hepatic decompensation; hypercalcemia; impaired liver function; and in patients who are easily sexually stimulated. Because of the potential risk of serious adverse health effects, methyltestosterone should not be used for enhancement of athletic performance or physique.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2948


Since the risks clearly outweigh the possible benefits in women who are or may become pregnant, methyltestosterone is contraindicated in such women. Women who become pregnant while receiving the drug should be informed of the potential hazard to the fetus.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2948


For more Drug Warnings (Complete) data for 17-METHYLTESTOSTERONE (20 total), please visit the HSDB record page.


4.4 Drug Indication

Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.


5.2 MeSH Pharmacological Classification

Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
METHYLTESTOSTERONE
5.3.2 FDA UNII
V9EFU16ZIF
5.3.3 Pharmacological Classes
Androgen [EPC]; Androstanes [CS]; Androgen Receptor Agonists [MoA]
5.4 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03B - Androgens

G03BA - 3-oxoandrosten (4) derivatives

G03BA02 - Methyltestosterone


G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03E - Androgens and female sex hormones in combination

G03EK - Androgens and female sex hormones in combination with other drugs

G03EK01 - Methyltestosterone


5.5 Absorption, Distribution and Excretion

Absorption

The methyl group aids to increase oral bioavailability.


Route of Elimination

90% urine / 10% feces


Absorbed from oral mucosa and gastrointestinal tract.

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 151


Sublingual methyltestosterone is absorbed faster and its bioavailability is double that from orally admin drug in humans...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 166


It is not known whether methyltestosterone is distributed into milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 2948


5.6 Metabolism/Metabolites

Hepatic. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).


17alpha-methyl-5beta-androstan-3alpha,16beta,17beta-triol...its 16-epimer 17alpha-methyl-5beta-androstan-3alpha,16alpha,17beta-triol...and 3alpha,17beta-dihydroxy-17alpha-methyl-5beta-androstan-16-one...have been identified as urinary metabolites of /17alpha-methyltestosterone/ of treated rabbits.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 230


5.7 Biological Half-Life

6-8 hours


2.5 to 3.5 hours

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 152


5.8 Mechanism of Action

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.