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Chemistry

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Also known as: 58-22-0, Androderm, Testim, Testosteron, Virosterone, Mertestate
Molecular Formula
C19H28O2
Molecular Weight
288.4  g/mol
InChI Key
MUMGGOZAMZWBJJ-DYKIIFRCSA-N
FDA UNII
3XMK78S47O

Testosterone
A potent androgenic steroid and major product secreted by the LEYDIG CELLS of the TESTIS. Its production is stimulated by LUTEINIZING HORMONE from the PITUITARY GLAND. In turn, testosterone exerts feedback control of the pituitary LH and FSH secretion. Depending on the tissues, testosterone can be further converted to DIHYDROTESTOSTERONE or ESTRADIOL.
Testosterone is an Androgen. The mechanism of action of testosterone is as an Androgen Receptor Agonist.
1 2D Structure

Testosterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
2.1.3 InChI Key
MUMGGOZAMZWBJJ-DYKIIFRCSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C
2.2 Other Identifiers
2.2.1 UNII
3XMK78S47O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Beta Hydroxy 4 Androsten 3 One

2. 17 Beta Hydroxy 8 Alpha 4 Androsten 3 One

3. 17-beta-hydroxy-4-androsten-3-one

4. 17-beta-hydroxy-8 Alpha-4-androsten-3-one

5. 8 Isotestosterone

6. 8-isotestosterone

7. Androderm

8. Androgel

9. Andropatch

10. Androtop

11. Histerone

12. Sterotate

13. Sustanon

14. Testim

15. Testoderm

16. Testolin

17. Testopel

18. Testosterone Sulfate

2.3.2 Depositor-Supplied Synonyms

1. 58-22-0

2. Androderm

3. Testim

4. Testosteron

5. Virosterone

6. Mertestate

7. Sustanon

8. Testoderm

9. Androgel

10. Androlin

11. Homosterone

12. Oreton

13. Testiculosterone

14. Synandrol F

15. Andropatch

16. Homosteron

17. Orquisteron

18. Perandren

19. Primotest

20. Primoteston

21. Sustanone

22. Testandrone

23. Testobase

24. Testopropon

25. Testosteroid

26. Andronaq

27. Andrusol

28. Relibra

29. Testogel

30. Testrone

31. Testryl

32. Teslen

33. Cristerona T

34. Testoviron T

35. Malerone

36. Neotestis

37. Testoviron

38. Trans-testosterone

39. Testoviron Schering

40. Cristerone T

41. Geno-cristaux Gremy

42. Testostosterone

43. Testolin

44. Libigel

45. Sustason 250

46. Percutacrine Androgenique

47. 17beta-hydroxyandrost-4-en-3-one

48. Oreton-f

49. Testoject-50

50. Testosterona

51. Testosteronum

52. Intrinsa

53. Striant

54. Andro 100

55. Testex

56. Testosterone Hydrate

57. Virormone

58. Beta Testosterone

59. Testro Aq

60. Malestrone (amps)

61. Malogen, Aquaspension Injection

62. Testosteronum [inn-latin]

63. Testosterona [inn-spanish]

64. Natesto

65. Vogelxo

66. Neo-hombreol F

67. Androst-4-en-17beta-ol-3-one

68. 17beta-hydroxy-4-androsten-3-one

69. 7-beta-hydroxyandrost-4-en-3-one

70. Col 1621

71. Delta4-androsten-17beta-ol-3-one

72. 17beta-hydroxyandrost-4-ene-3-one

73. 17-beta-hydroxyandrost-4-en-3-one

74. 4-androsten-17beta-ol-3-one

75. Testosterone Ciii

76. 17-hydroxy-(17beta)-androst-4-en-3-one

77. 17beta-hydroxy-delta(sup4)-androsten-3-one

78. Delta(sup 4)-androsten-17(beta)-ol-3-one

79. (+)-testosterone

80. 17-hydroxy-(17-beta)-androst-4-en-3-one

81. 17-beta-hydroxy-delta(sup 4)-androsten-3-one

82. Androst-4-en-3-one, 17beta-hydroxy-

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

84. Androst-4-en-3-one, 17-beta-hydroxy-

85. Chebi:17347

86. (17beta)-17-hydroxyandrost-4-en-3-one

87. (8r,9s,10r,13s,14s,17s)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

88. Neo-testis

89. Testoderm Tts

90. 3xmk78s47o

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

92. Nsc-9700

93. Testopel Pellets

94. Cdb 111c

95. Testosterone And Its Esters

96. Halotensin

97. Fortesta

98. Livensa

99. Nasobol

100. Axiron

101. Tefina

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

103. Compleotrt

104. Cp 601b

105. 17.beta.-hydroxyandrost-4-en-3-one

106. (8alpha,10alpha,13alpha,14beta,17alpha)-17-hydroxyandrost-4-en-3-one

107. Androderm (tn)

108. Androgel 1%

109. 17.beta.-testosterone

110. Androgel (tn)

111. Smr000058344

112. Ccris 574

113. Striant (tn)

114. Bio-t-gel

115. Aa 2500

116. Testim (tn)

117. Androgel 1.62%

118. Hsdb 3398

119. Nsc 9700

120. Einecs 200-370-5

121. Testosterone (jan/usp)

122. Androst-4-en-3-on-17b-ol

123. Chembl386630

124. Component Of Duogen (salt/mix)

125. Component Of Tostrex (salt/mix)

126. Component Of Di-met (salt/mix)

127. Unii-3xmk78s47o

128. Component Of Intrinsa (salt/mix)

129. Epitestosteron

130. Lumitestosteron

131. 4-androsten-17.beta.-ol-3-one

132. 4-androsten-3-one-17.beta.-ol

133. Tostrelle

134. Tostrex

135. Viatrel

136. Component Of Di-genik (salt/mix)

137. 4-androsten-3-one, 17b-hydroxy-

138. Testosterone [usp:inn:ban]

139. 9b-testosterone

140. Component Of Mal-o-fem (salt/mix)

141. Testosterone [androgenic Steroids, Anabolic]

142. 4-androstene-17beta-ol-3-one

143. 17b-hydroxy-4-androsten-3-one

144. Delta4-androsten-17b-ol-3-one

145. Lpcn 1021

146. Testosterone, 1

147. 3kdm

148. 17b-testosterone

149. 17-.beta.-hydroxyandrost-4-en-3-one

150. Ncgc00091018-01

151. 8-iso-testosterone

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

153. (+-)-testosterone

154. Axiron (tn)

155. Cmc_13449

156. 13-iso-testosterone

157. Androlan

158. Mpp10

159. 9b,10a-testosterone

160. 17.beta.-hydroxy-.delta.4-androsten-3-one

161. Android-t

162. 17-hydroxyandrost-4-en-3-one, (17.beta.)-

163. (+-)-retrotestosterone

164. Testosterone, >=98%

165. Testosterone [mi]

166. Dsstox_cid_2371

167. Testosterone [inn]

168. Testosterone [jan]

169. Epitope Id:135865

170. Ec 200-370-5

171. Testosterone [hsdb]

172. Testosterone [inci]

173. Testosterone Ep Impurity C

174. (+-)-8-iso-testosterone

175. Schembl8452

176. Dsstox_rid_76563

177. Testosterone [vandf]

178. Dsstox_gsid_22371

179. Testosterone [mart.]

180. 4-androsten-3-one-17b-ol

181. Mls000563091

182. Mls001032098

183. Mls001306401

184. Mls001424262

185. Mls002174283

186. Bidd:er0555

187. Testosterone [who-dd]

188. D4-androsten-17b-ol-3-one

189. Androst-4-en-17b-ol-3-one

190. Bdbm8885

191. Gtpl2858

192. Androst-4-ene-17b-ol-3-one

193. Testosterone [ema Epar]

194. Dtxsid8022371

195. 17-hydroxy-d4-androsten-3-one

196. 17-hydroxy-androst-4-en-3-one

197. 17beta-hydroxy-4-androsten-3one

198. Testosterone [green Book]

199. Testosterone, Cell Culture Tested

200. 17b-hydroxy-androst-4-en-3-on

201. 17b-hydroxy-d4-androsten-3-one

202. 17b-hydroxyandrost-4-ene-3-one

203. 1i37

204. 17a-hydroxy-androst-4-en-3-one

205. 17b-hydroxy-androst-4-en-3-one

206. Hms2052n11

207. Hms2272b03

208. Hms2272p03

209. Testosterone [ep Impurity]

210. Testosterone [orange Book]

211. Testosterone [ep Monograph]

212. (8r,9s,10r,13s,14s,17s)-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

213. 17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

214. Testosterone [usp Monograph]

215. Tox21_200689

216. Hy-15554a

217. Lmst02020002

218. Rb3046

219. 17b-hydroxy-8a-androst-4-en-3-one

220. Rac-17b-hydroxy-androst-4-en-3-one

221. Akos015894897

222. Zinc118912393

223. 17a-hydroxy-13a-androst-4-en-3-one

224. 17a-hydroxy-14b-androst-4-en-3-one

225. 17b-hydroxy-13a-androst-4-en-3-one

226. Ccg-101189

227. Cs-1415

228. Db00624

229. Nc00439

230. Cas-58-22-0

231. Testosterone 1.0 Mg/ml In Acetonitrile

232. Testosterone 100 Microg/ml In Methanol

233. (17?)-17-hydroxyandrost-4-en-3-one

234. 17b-hydroxy-(8a)-androst-4-en-3-one

235. 17b-hydroxy-(9b)-androst-4-en-3-one

236. Ncgc00258243-01

237. (17b)-17-hydroxy-androst-4-en-3-one

238. 17a-hydroxy-(13a)-androst-4-en-3-one

239. 17b-hydroxy-(10a)-androst-4-en-3-one

240. 17b-hydroxy-(13a)-androst-4-en-3-one

241. Ac-14899

242. Cpd000058344

243. Smr001261453

244. Testosterone 1000 Microg/ml In Methanol

245. Testosterone, Purum, >=99.0% (hplc)

246. Testosterone 100 Microg/ml In Acetonitrile

247. Rac-17b-hydroxy-(13a)androst-4-en-3-one

248. Rac-17b-hydroxy-(8a)-androst-4-en-3-one

249. T0027

250. 17b-hydroxy-(8a,10a)-androst-4-en-3-one

251. 17b-hydroxy-(9b,10a)-androst-4-en-3-one

252. Bim-0061761.0001

253. C00535

254. D00075

255. Rac-17b-hydroxy-(9b,10a)androst-4-en-3-one

256. S00309

257. Ab00973630-03

258. Testosterone, Vetranal(tm), Analytical Standard

259. 003t654

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

261. Q-101251

262. Q1318776

263. B5dee83f-632b-48a1-a0ed-a51e7f13df2e

264. Testosterone Enantate Impurity D [ep Impurity]

265. Testosterone Propionate Impurity C [ep Impurity]

266. Testosterone, European Pharmacopoeia (ep) Reference Standard

267. Testosterone Solution, 1.0 Mg/ml In 1,2-dimethoxyethane, Drug Standard

268. Testosterone; 4-androsten-17?-ol-3-one; 17?-hydroxy-4-androsten-3-one

269. Testosterone For Impurity D Identification, European Pharmacopoeia (ep) Reference Standard

270. Testosterone For System Suitability, European Pharmacopoeia (ep) Reference Standard

271. (1s,2r,10r,11s,14s,15s)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one

272. 1050678-68-6

273. 17?-hydroxyandrost-4-en-3-one; Epitestosterone; 17-epi-testosterone; 17?-cis-testosterone; 4-androstene-17?-ol-3-one; Isotestosterone

274. Testosterone Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 288.4 g/mol
Molecular Formula C19H28O2
XLogP33.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass288.208930132 g/mol
Monoisotopic Mass288.208930132 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity508
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 14  
Drug NameAndroderm
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelANDRODERM (testosterone transdermal system) is designed to delivertestosteronecontinuously for 24 hours following application to intact, non-scrotal skin (e.g., back, abdomen, thighs, upper arms). Two strengths of ANDRODERM are available that del...
Active IngredientTestosterone
Dosage FormFilm, extended release
RouteTransdermal
Strength2mg/24hr; 4mg/24hr
Market StatusPrescription
CompanyWatson Labs

2 of 14  
Drug NameAndrogel
PubMed HealthTestosterone (On the skin)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelAndroGel (testosterone gel) 1% is a clear, colorle hydroalcoholic gel containing testosterone. The active pharmacologic ingredient in AndroGel 1% is testosterone, an androgen. Testosterone USP is a white to practically white crystalline powder chem...
Active IngredientTestosterone
Dosage FormGel; Gel, metered
RouteTransdermal
Strength1.62% (20.25mg/1.25gm actuation); 1.62% (20.25mg/1.25gm packet); 12.5mg/1.25gm actuation; 50mg/5gm packet; 1.62% (40.5mg/2.5gm packet); 25mg/2.5gm packet
Market StatusPrescription
CompanyAbbvie

3 of 14  
Drug NameAxiron
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelAXIRON (testosterone) topical solution is a clear, colorle, single phase solution containing 30 mg of testosterone in 1.5 mL of AXIRON solution for topical administration through the axilla. The active pharmacologic ingredient in AXIRON is testoste...
Active IngredientTestosterone
Dosage FormSolution, metered
RouteTransdermal
Strength30mg/1.5ml actuation
Market StatusPrescription
CompanyEli Lilly And

4 of 14  
Drug NameFortesta
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelFORTESTA is a clear, colorle, odorle, gel containing testosterone. FORTESTA is available in a metered-dose pump. Each pump actuation provides 10 mg of testosterone and each container is capable of dispensing 120 pump actuations. One pump actuatio...
Active IngredientTestosterone
Dosage FormGel, metered
RouteTransdermal
Strength10mg/0.5gm actuation
Market StatusPrescription
CompanyEndo Pharms

5 of 14  
Drug NameStriant
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelStriant (testosterone buccal system) is designed to adhere to the gum or inner cheek. It provides a controlled and sustained release of testosterone through the buccal mucosa as the buccal system gradually hydrates. Insertion of Striant twice a d...
Active IngredientTestosterone
Dosage FormTablet, extended release
RouteBuccal
Strength30mg
Market StatusPrescription
CompanyAuxilium Pharms

6 of 14  
Drug NameTestim
Drug LabelStructure Image...
Active IngredientTestosterone
Dosage FormGel
RouteTransdermal
Strength1% (50mg/5gm packet)
Market StatusPrescription
CompanyAuxilium Pharms

7 of 14  
Drug NameTestosterone
Drug LabelStructure Image...
Active IngredientTestosterone
Dosage FormGel; Gel, metered
RouteTransdermal
Strength12.5mg/1.25gm actuation; 50mg/5gm packet; 25mg/2.5gm packet
Market StatusPrescription
CompanyTeva Pharms; Perrigo Israel

8 of 14  
Drug NameAndroderm
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelANDRODERM (testosterone transdermal system) is designed to delivertestosteronecontinuously for 24 hours following application to intact, non-scrotal skin (e.g., back, abdomen, thighs, upper arms). Two strengths of ANDRODERM are available that del...
Active IngredientTestosterone
Dosage FormFilm, extended release
RouteTransdermal
Strength2mg/24hr; 4mg/24hr
Market StatusPrescription
CompanyWatson Labs

9 of 14  
Drug NameAndrogel
PubMed HealthTestosterone (On the skin)
Drug ClassesEndocrine-Metabolic Agent
Drug LabelAndroGel (testosterone gel) 1% is a clear, colorle hydroalcoholic gel containing testosterone. The active pharmacologic ingredient in AndroGel 1% is testosterone, an androgen. Testosterone USP is a white to practically white crystalline powder chem...
Active IngredientTestosterone
Dosage FormGel; Gel, metered
RouteTransdermal
Strength1.62% (20.25mg/1.25gm actuation); 1.62% (20.25mg/1.25gm packet); 12.5mg/1.25gm actuation; 50mg/5gm packet; 1.62% (40.5mg/2.5gm packet); 25mg/2.5gm packet
Market StatusPrescription
CompanyAbbvie

10 of 14  
Drug NameAxiron
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelAXIRON (testosterone) topical solution is a clear, colorle, single phase solution containing 30 mg of testosterone in 1.5 mL of AXIRON solution for topical administration through the axilla. The active pharmacologic ingredient in AXIRON is testoste...
Active IngredientTestosterone
Dosage FormSolution, metered
RouteTransdermal
Strength30mg/1.5ml actuation
Market StatusPrescription
CompanyEli Lilly And

11 of 14  
Drug NameFortesta
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelFORTESTA is a clear, colorle, odorle, gel containing testosterone. FORTESTA is available in a metered-dose pump. Each pump actuation provides 10 mg of testosterone and each container is capable of dispensing 120 pump actuations. One pump actuatio...
Active IngredientTestosterone
Dosage FormGel, metered
RouteTransdermal
Strength10mg/0.5gm actuation
Market StatusPrescription
CompanyEndo Pharms

12 of 14  
Drug NameStriant
PubMed HealthTestosterone
Drug ClassesAndrogen, Endocrine-Metabolic Agent
Drug LabelStriant (testosterone buccal system) is designed to adhere to the gum or inner cheek. It provides a controlled and sustained release of testosterone through the buccal mucosa as the buccal system gradually hydrates. Insertion of Striant twice a d...
Active IngredientTestosterone
Dosage FormTablet, extended release
RouteBuccal
Strength30mg
Market StatusPrescription
CompanyAuxilium Pharms

13 of 14  
Drug NameTestim
Drug LabelStructure Image...
Active IngredientTestosterone
Dosage FormGel
RouteTransdermal
Strength1% (50mg/5gm packet)
Market StatusPrescription
CompanyAuxilium Pharms

14 of 14  
Drug NameTestosterone
Drug LabelStructure Image...
Active IngredientTestosterone
Dosage FormGel; Gel, metered
RouteTransdermal
Strength12.5mg/1.25gm actuation; 50mg/5gm packet; 25mg/2.5gm packet
Market StatusPrescription
CompanyTeva Pharms; Perrigo Israel

4.2 Therapeutic Uses

Androgens

National Library of Medicine's Medical Subject Headings. Testosterone. Online file (MeSH, 2016). Available from, as of November 28, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Testosterone is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=testosterone&Search=Search


In males, testosterone is used for the management of congenital or acquired primary hypogonadism such as that resulting from orchiectomy or from testicular failure caused by cryptorchidism, bilateral torsion, orchitis, or vanishing testis syndrome. Testosterone also is used in males for the management of congenital or acquired hypogonadotropic hypogonadism such as that resulting from idiopathic gonadotropin or gonadotropin-releasing hormone (luteinizing hormone releasing hormone) deficiency or from pituitary-hypothalamic injury caused by tumors, trauma, or radiation. If any of these conditions occur before puberty, androgen replacement therapy will be necessary during adolescence for the development of secondary sexual characteristics and prolonged therapy will be required to maintain these characteristics. Prolonged androgen therapy also is required to maintain sexual characteristics in other males who develop testosterone deficiency after puberty. /Included in US product labeling/

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3131


When the diagnosis is well established, testosterone may be used to stimulate puberty in carefully selected males with delayed puberty. These males usually have a family history of delayed puberty that is not caused by a pathologic disorder. Brief treatment with conservative doses of an androgen may occasionally be justified in these males if they do not respond to psychologic support. Because androgens may adversely affect bone maturation in these prepubertal males, this potential risk should be fully discussed with the patient and his parents prior to initiation of androgen therapy. If androgen therapy is initiated in these prepubertal males, radiographs of the hand and wrist should be obtained at 6-month intervals to determine the effect of therapy on the epiphyseal centers. Testosterone is designated an orphan drug by the FDA for use in this condition. /Included in US product labeling/

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3132


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


4.3 Drug Warning

/BOXED WARNING/ WARNING: SECONDARY EXPOSURE TO TESTOSTERONE. Virilization has been reported in children who were secondarily exposed to testosterone gel. Children should avoid contact with unwashed or unclothed application sites in men using testosterone gel. Healthcare providers should advise patients to strictly adhere to recommended instructions for use.

NIH; DailyMed. Current Medication Information for Androgel (Testosterone Gel) (Updated: January 2015). Available from, as of April 5, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a8253ce7-77df-49d4-8077-816cf4dc234f


Cardiovascular events, including MI or stroke, have been reported during postmarketing experience with testosterone transdermal system (Androderm). Testosterone should be used with caution in patients at high risk for cardiovascular disease (e.g., older men, those with diabetes mellitus or obesity). Patients should be advised to immediately report symptoms suggestive of MI or stroke (e.g., chest pain, shortness of breath, unilateral weakness, difficulty talking) to their clinician.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3135-6


Venous thromboembolic events, including deep-vein thrombosis (DVT) and pulmonary embolism (PE), have been reported during postmarketing experience with testosterone preparations, including testosterone transdermal system (Androderm). Patients reporting symptoms of pain, edema, warmth, and erythema in a lower extremity or presenting with acute shortness of breath should be evaluated for possible DVT or PE, respectively. If venous thromboembolism is suspected, testosterone therapy should be discontinued and appropriate evaluation and management should be initiated.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3136


Testosterone should be used with caution in patients with cardiac, renal, and/or hepatic dysfunction since edema may occur as a result of sodium and water retention. Edema, with or without congestive heart failure, may be a serious complication in patients with preexisting cardiac, renal, and/or hepatic disease. If edema occurs during testosterone therapy and it is considered a serious complication, the drug should be discontinued; diuretic therapy may also be necessary.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3136


For more Drug Warnings (Complete) data for Testosterone (34 total), please visit the HSDB record page.


4.4 Drug Indication

Testosterone is indicated to treat primary hypogonadism and hypogonadotropic hypogonadism.


FDA Label


Intrinsa is indicated for the treatment of hypoactive sexual desire disorder (HSDD) in bilaterally oophorectomised and hysterectomised (surgically induced menopause) women receiving concomitant estrogen therapy.


Livensa is indicated for the treatment of hypoactive sexual desire disorder (HSDD) in bilaterally oophorectomised and hysterectomised (surgically induced menopause) women receiving concomitant estrogen therapy.


Treatment of dry eye disease


Treatment of male hypogonadism


Hypoactive sexual desire disorder


Hypoactive sexual desire disorder


Treatment of male hypogonadism


5 Pharmacology and Biochemistry
5.1 Pharmacology

Testosterone antagonizes the androgen receptor to induce gene expression that causes the growth and development of masculine sex organs and secondary sexual characteristics. The duration of action of testosterone is variable from patient to patient with a half life of 10-100 minutes. The therapeutic index is wide considering the normal testosterone levels in an adult man range from 300-1000ng/dL. Counsel patients regarding the risk of secondary exposure of testosterone topical products to children.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TESTOSTERONE
5.3.2 FDA UNII
3XMK78S47O
5.3.3 Pharmacological Classes
Androgen [EPC]; Androstanes [CS]; Androgen Receptor Agonists [MoA]
5.4 ATC Code

G03BA03


G03BA03


G03BA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03B - Androgens

G03BA - 3-oxoandrosten (4) derivatives

G03BA03 - Testosterone


5.5 Absorption, Distribution and Excretion

Absorption

A single 100mg topical dose of testosterone has an AUC of 104255521ng\*h/dL and a Cmax of 573284ng/dL. Testosterone is approximately 10% bioavailable topically.


Route of Elimination

90% of an intramuscular dose is eliminated in urine, mainly as glucuronide and sulfate conjugates. 6% is eliminated in feces, mostly as unconjugated metabolites.


Volume of Distribution

The volume of distribution of testosterone in elderly men is 80.3624.51L.


Clearance

The mean metabolic clearance in middle aged men is 81264L/day.


Testosterone is absorbed systemically through the skin following topical application as a gel or transdermal system. Following topical application of a hydroalcoholic gel formulation of testosterone (AndroGel, Testim) to the skin, the gel quickly dries on the skin surface, which serves as a reservoir for sustained release of the hormone into systemic circulation. Approximately 10% of a testosterone dose applied topically to the skin as a 1% gel is absorbed percutaneously into systemic circulation. The manufacturer of AndroGel states that increases in serum testosterone concentrations were apparent within 30 minutes of topical application of a 100-mg testosterone dose of the 1% gel, with physiologic concentrations being achieved in most patients within 4 hours (pretreatment concentrations were not described); percutaneous absorption continues for the entire 24-hour dosing interval. Serum testosterone concentrations approximate steady-state levels by the end of the initial 24 hours and are at steady state by the second or third day of dosing of the 1% gel. With daily topical application of the 1% gel (AndroGel), serum testosterone concentrations 30, 90, and 180 days after initiating treatment generally are maintained in the eugonadal range. Administration of 10 or 5 g of AndroGel daily results in average daily serum testosterone concentrations of 794 or 566 ng/dL, respectively, at day 30. Following discontinuance of such topical therapy, serum testosterone concentrations remain within the normal range for 24-48 hours but return to pretreatment levels by the fifth day after the last application.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3137


With topical application of a transdermal preparation, the extent of percutaneous testosterone absorption varies according to the site of application, possibly secondary to regional differences in skin permeability, cutaneous blood flow, and/or degree of adhesion between the transdermal system and skin. In one study in which transdermal systems were applied to the abdomen, back, chest, shin, thigh, or upper arm, serum hormone profiles were qualitatively similar with each site, but steady-state serum concentrations showed significant differences, decreasing in order with the back, thigh, upper arm, abdomen, chest, and shin. Application of Androderm transdermal systems to the abdomen, back, thighs, or upper arms results in achievement of similar serum testosterone concentration profiles, and these sites are recommended as optimal for rotation of application sites during chronic therapy. Daily nighttime (at approximately 10 p.m.) application of Androderm transdermal system results in a serum testosterone concentration profile that mimics the endogenous diurnal pattern in healthy young men. In one study, showering 3 hours after application of Androderm decreased peak plasma concentrations of testosterone by 0.4% compared with not showering 3 hours after application of the transdermal system. In addition, showering 3 hours after transdermal system application did not substantially alter the systemic exposure of testosterone.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3137-8


Following topical application of transdermal systems of testosterone, the hormone is absorbed percutaneously into systemic circulation. Although interindividual variation in percutaneous testosterone absorption occurs, serum testosterone concentrations achieved with recommended dosages of transdermal systems of the drug generally reach the normal range during the first day of dosing and are maintained during continuous dosing without accumulation. Average daily serum testosterone concentrations in patients receiving Androderm reportedly are 498 ng/dL at steady state. Mean ratios of testosterone to DHT are within the normal range.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3137


Esterification of testosterone generally results in less polar compounds. The enanthate ester of testosterone is absorbed slowly from the lipid tissue phase at the IM injection site, achieving peak serum concentrations about 72 hours after IM injection; thus, this preparation has a prolonged duration of action (i.e., up to 2-4 weeks) following IM administration. Because IM injection of testosterone esters causes local irritation, the rate of absorption may be erratic. /Testosterone esters/

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3137


For more Absorption, Distribution and Excretion (Complete) data for Testosterone (9 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). Testosterone can be hydroxylated at a number of positions by CYP3A4, CYP2B6, CYP2C9, and CYP2C19; glucuronidated by UGT2B17; sulfated; converted to estradiol by aromatase; converted to dihydrotestosterone (DHT) by 5-reductase; metabolized to androstenedione by CYP3A4, CYP2C9, and CYP2C19; or converted to DHT glucuronide. Androstenedione undergoes metabolism by aromatase to form estrone, which undergoes a reversible reaction to form estradiol. Androstenedione can also be converted to 5-androstanedione by 5-reductase, which can be further metabolized to 5-androsterone. DHT can be glucuronidated or sulfated, or metabolized to 5-androstanediol, androstane-3,17-diol, or androstane-3,17-diol. DHT can also be reversibly converted to 5-androstanedione.


Extensive reductive metabolism of testosterone occurs not only in the liver, but also in a variety of extrahepatic tissues, especially in target organs of the sex hormones; the ultimately effective physiological androgen is formed in the target tissues. Testosterone metabolism occurs not only in the prostate and seminal vesicles but also in rat uterus, rabbit placenta, rodent testis and primate brain. In rats, the small intestine is also capable of metabolizing testosterone.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 536 (1979)


It is transformed to 5-alpha-dehydrotestosterone in target organs such as the prostate, sebaceous glands and seminal vesicles; only the latter compound binds to the androgen-receptor site in these target organs.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 536 (1979)


Large quantitative differences in testosterone metabolism are evident between female and male rats. The reason for this phenomenon is that many steroid-metabolizing enzymes in rats are either androgen- or estrogen-dependent; the sex hormones thus act in an inductive or a repressive manner.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 536 (1979)


Esters of testosterone, such as the propionate, the heptanoate, the cypionate, the valerate, the isovalerate, the enanthate and the undecanoate, are partially cleaved in vivo to release the parent compound. This has been demonstrated by oral administration of testosterone undecanoate in oily solution to rats: most of the compound is converted within the intestinal wall, the first step being partial splitting off of the fatty acid moiety. The non-metabolized portion, however, and the metabolite 5-alpha-dihydrotestosterone undecanoate, are absorbed via the lymphatic system and made available for androgenic action to the organism. /Testosterone esters/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 537 (1979)


For more Metabolism/Metabolites (Complete) data for Testosterone (6 total), please visit the HSDB record page.


Testosterone has known human metabolites that include 15-Hydroxytestosterone, 15beta-Hydroxytestosterone, 16-Hydroxytestosterone, 16beta-Hydroxytestosterone, 2alpha-Hydroxytestosterone, 2beta-Hydroxytestosterone, 6alpha-Hydroxytestosterone, Androstenedione, and Testosterone sulfate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The half life of testosterone is highly variable, ranging from 10-100 minutes.


The plasma half-life of testosterone reportedly ranges from 10-100 minutes. The plasma half-life of testosterone cypionate after IM injection is approximately 8 days. Following removal of an Androderm transdermal system, plasma testosterone concentrations decline with an apparent half-life of approximately 70 minutes ... .

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3138


5.8 Mechanism of Action

The androgen receptor exists in the cytoplasm bound to the heat shock proteins HSP90, HSP70, and other chaperones. After binding to an androgen, the androgen receptor dissociates from HSP90 and undergoes a conformational change to slow the rate of dissociation from the androgen receptor. The androgen-receptor complex is transported into the nucleus where it binds to DNA and recruits other transcriptional regulators to form a pre-initiation complex and eventually induce expression of specific genes. Testosterone and its active metabolite dihydrotestosterone (DHT) antagonize the androgen receptor to develop masculine sex organs including the prostate, seminal vesicles, penis, and scrotum. Antagonism of the androgen receptor is also responsible for the development of secondary sexual characteristics including facial and body hair, enlargement of the larynx, thickening of the vocal cords, and changes in muscle and fat distribution.


Low-grade chronic inflammation is commonly found in patients with polycystic ovary syndrome (PCOS) who exhibit hyperandrogenism or hyperandrogenemia. Clinical studies have shown that hyperandrogenemia is closely correlated with low-grade chronic inflammation. However, the mechanism underlying this correlation remains unclear. Recent studies have suggested that adipocytes increase the production of proinflammatory mediators such as interleukin-6 (IL-6) and macrophage chemotactic protein-1 (MCP-1) when the inflammatory signal transduction cascade system is activated by external stimuli. The present study aimed to evaluate the effects of testosterone on the innate signalling and expression of proinflammatory mediators in 3T3-L1 adipocytes, which were or were not induced by lipopolysaccharide (LPS). The effects of testosterone on the expression of proinflammatory mediators, nuclear factor-kappaB (NF-kappaB), and extracellular signal-regulated kinase 1/2 (ERK1/2) signalling pathways were investigated using an enzyme-linked immunosorbent assay, reverse transcriptase-polymerase chain reaction, western blot analysis and an electrophoresis mobility shift assay. Testosterone induces IL-6 and MCP-1, and enhances LPS-induction of IL-6 and MCP-1. However, the effects are not simply additive, testosterone significantly enhanced the effects of LPS-induced inflammation factors. Testosterone induces the phosphorylation of ERK1/2 and NF-kappaB. The effect of testosterone on the expression of IL-6 and MCP-1 is inhibited by PD98059, an ERK1/2 inhibitor, and PDTC, an NF-kappaB inhibitor. The results indicate that testosterone enhances LPS-induced IL-6 and MCP-1 expression by activating the ERK1/2/NF-kappaB signalling pathways in 3T3-L1 adipocytes.

PMID:25738264 Su C et al; Mol Med Rep 12 (1): 696-704 (2015)


Androgens reportedly stimulate the production of erythrocytes, apparently by enhancing the production of erythropoietic stimulating factor.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 3137


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15-Jan-2021
29-Nov-2024
KGS
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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 2MG/24HR **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20489

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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 4MG/24HR **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20489

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DOSAGE - GEL, METERED;NASAL - 5.5MG/0.122GM A...DOSAGE - GEL, METERED;NASAL - 5.5MG/0.122GM ACTUATION

USFDA APPLICATION NUMBER - 205488

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DOSAGE - GEL, METERED;TRANSDERMAL - 12.5MG/1....DOSAGE - GEL, METERED;TRANSDERMAL - 12.5MG/1.25GM ACTUATION

USFDA APPLICATION NUMBER - 21015

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DOSAGE - GEL;TRANSDERMAL - 25MG/2.5GM PACKET

USFDA APPLICATION NUMBER - 21015

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DOSAGE - GEL;TRANSDERMAL - 50MG/5GM PACKET

USFDA APPLICATION NUMBER - 21015

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DOSAGE - GEL;TRANSDERMAL - 50MG/5GM PACKET

USFDA APPLICATION NUMBER - 21454

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DOSAGE - TABLET, EXTENDED RELEASE;BUCCAL - 30...DOSAGE - TABLET, EXTENDED RELEASE;BUCCAL - 30MG

USFDA APPLICATION NUMBER - 21543

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DOSAGE - GEL, METERED;TRANSDERMAL - 1.62% (20...DOSAGE - GEL, METERED;TRANSDERMAL - 1.62% (20.25MG/1.25GM ACTUATION)

USFDA APPLICATION NUMBER - 22309

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DOSAGE - GEL;TRANSDERMAL - 1.62% (40.5MG/2.5G...DOSAGE - GEL;TRANSDERMAL - 1.62% (40.5MG/2.5GM PACKET)

USFDA APPLICATION NUMBER - 22309

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DOSAGE - SOLUTION, METERED;TRANSDERMAL - 30MG...DOSAGE - SOLUTION, METERED;TRANSDERMAL - 30MG/1.5ML ACTUATION **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22504

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