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10 Related Intermediates

Chemistry

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Also known as: Dhea, Prasterone, 53-43-0, Dehydroisoandrosterone, Androstenolone, Trans-dehydroandrosterone

Molecular Formula

C₁₉H₂₈O₂

Molecular Weight

288.4 g/mol

InChI Key

FMGSKLZLMKYGDP-USOAJAOKSA-N

FDA UNII

459AG36T1B

A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.

1 2D Structure

CAS 53-43-0

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-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/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

2.1.3 InChI Key

FMGSKLZLMKYGDP-USOAJAOKSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)O)C

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C

2.2 Other Identifiers

2.2.1 UNII

459AG36T1B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5 Androsten 3 Beta Hydroxy 17 One

2. 5 Androsten 3 Ol 17 One

3. 5-androsten-3-beta-hydroxy-17-one

4. 5-androsten-3-ol-17-one

5. Androstenolone

6. Dehydroisoandrosterone

7. Dhea

8. Prasterone

9. Prasterone, 3 Alpha Isomer

10. Prasterone, 3 Alpha-isomer

2.3.2 Depositor-Supplied Synonyms

1. Dhea

2. Prasterone

3. 53-43-0

4. Dehydroisoandrosterone

5. Androstenolone

6. Trans-dehydroandrosterone

7. Psicosterone

8. Diandron

9. Diandrone

10. 3beta-hydroxyandrost-5-en-17-one

11. 17-hormoforin

12. Prestara

13. 17-chetovis

14. Andrestenol

15. Intrarosa

16. 5-dehydroepiandrosterone

17. 3-beta-hydroxy-5-androsten-17-one

18. Dehydro-epi-androsterone

19. Siscelar Plus

20. (+)-dehydroisoandrosterone

21. 5,6-didehydroisoandrosterone

22. Dehydroepiandrosterone (dhea)

23. Prasteronum

24. 5,6-dehydroisoandrosterone

25. Astenile

26. Prasterona

27. Vaginorm

28. Epiandrosterone, 5-dehydro-

29. Caswell No. 051f

30. 5,6-dehydroisoandrostorone

31. 3beta-hydroxy-5-androsten-17-one

32. Biolaif

33. Ccris 3277

34. Deandros

35. 5-androsten-3beta-ol-17-one

36. (3-beta)-3-hydroxyandrost-5-en-17-one

37. Dehydroisoandosterone

38. Em-760

39. Gl 701

40. Androst-5-en-17-one, 3-hydroxy-, (3beta)-

41. Epa Pesticide Chemical Code 126510

42. (3beta)-3-hydroxyandrost-5-en-17-one

43. Nsc 9896

44. Nsc-9896

45. Androst-5-en-17-one, 3-hydroxy-, (3.beta.)-

46. Androst-5-en-17-one, 3-beta-hydroxy-

47. Chembl90593

48. (3s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

49. Androst-5-en-17-one, 3-hydroxy-, (3b)-

50. Chebi:28689

51. D5-androsten-3beta-ol-17-one

52. Androst-5-ene-3beta-ol-17-one

53. Nsc9896

54. 459ag36t1b

55. 3beta-hydroxy-d5-androsten-17-one

56. 3-beta-hydroxyandrost-5-en-17-one

57. 3.beta.-hydroxyandrost-5-en-17-one

58. Dsstox_cid_379

59. Dsstox_rid_75553

60. Dsstox_gsid_20379

61. (3s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17(2h)-one

62. And

63. Prasterone [inn]

64. Prasteronum [inn-latin]

65. Prasterona [inn-spanish]

66. Cas-53-43-0

67. (1s,2r,5s,10r,11s,15s)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

68. Smr000059075

69. Androst-5-en-17-one, 3.beta.-hydroxy-

70. Sr-01000075815

71. Prasterone [usan:inn]

72. Einecs 200-175-5

73. Brn 2058110

74. 5-androsten-3.beta.-ol-17-one

75. Anastar

76. Inflabloc

77. Aslera

78. Unii-459ag36t1b

79. Fidelin T

80. Dhea; Prasterone

81. Ncgc00093802-04

82. Ncgc00093802-06

83. Dehydroepiandosterone

84. Biolaif (tn)

85. Androst-5-en-17-one, 3beta-hydroxy-

86. Dehydroepiandrostenedione

87. 5-dehydro-epiandrosterone

88. Prasterone (usan/inn)

89. Trans-de-hydroandrosterone

90. Prasterone [inci]

91. Prasterone [usan]

92. Bmse000665

93. Ec 200-175-5

94. Prasterone [mart.]

95. Androsten-3beta-ol-17-one

96. Prasterone [who-dd]

97. Androst-5-en-17-one, 3-hydroxy-, (3-beta)-

98. Bidd:pxr0080

99. Lopac0_000368

100. Schembl24156

101. 4-08-00-00994 (beilstein Handbook Reference)

102. Mls001066350

103. Mls001333231

104. Mls001333232

105. Mls001424274

106. 5-androsten-3b-ol-17-one

107. D5-androsten-3b-ol-17-one

108. Gtpl2370

109. Androst-5-ene-3b-ol-17-one

110. Dtxsid4020379

111. Prasterone [orange Book]

112. 3b-hydroxyandrost-5-en-17-one

113. 5-androsten-3-beta-ol-17-one

114. Bcpe00002

115. 3b-hydroxy-d5-androsten-17-one

116. 3beta-hyroxyandrost-5-en-17-one

117. Bcpp000260

118. Dehydroepiandrosterone [mi]

119. El-10

120. Hms2052p11

121. Hms2090c04

122. Hms2232k11

123. Im 28

124. Trans-dehydroandrosterone, >=99%

125. 3-beta-hydroxy-5-androsten-17-on

126. Act02646

127. Amy25708

128. Bcp02453

129. Ipl-1001

130. Zinc3807917

131. 3beta-hydroxy-androst-5-en-17-one

132. 3beta-hydroxyandrost-5-ene-17-one

133. Tox21_111222

134. Tox21_201996

135. Tox21_302761

136. Bdbm50223368

137. Cmc_13435

138. Delta5-androsten-3-beta-ol-17-one

139. Dl-373

140. Gl-701

141. Lmst02020021

142. Pb-007

143. S2604

144. Dehydroepiandrosterone [vandf]

145. 5-androsten-3beta-ol-17-one; Dhea

146. Akos007930299

147. Akos015951378

148. Prasterone 100 Microg/ml In Methanol

149. Tox21_111222_1

150. Bcp9000602

151. Ccg-101190

152. Cs-1667

153. Db01708

154. Fd12003

155. Gs-0906

156. Ip-1001

157. Nc00440

158. Sh-k-04828

159. Ncgc00093802-09

160. Ncgc00256412-01

161. Ncgc00259545-01

162. (1s,5s,11s,15s,2r,10r)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15> ]heptadec-7-en-14-one

163. (3beta)-3-hydroxyandrost-5-ene-17-one

164. Ac-28716

165. Hy-14650

166. Nci60_042215

167. Prasterone (dhea; Dehydroepiandrosterone)

168. (3beta)-3-hydroxy-androst-5-en-17-one

169. D0044

170. Eu-0100368

171. Androst-5-en-17-one, 3beta-hydroxy- (8ci)

172. C01227

173. D 4000

174. D-0340

175. D08409

176. (3alpha,8alpha)-3-hydroxyandrost-5-en-17-one

177. Ab00375810-06

178. Ab00375810_09

179. Q408376

180. Sr-01000075815-1

181. Sr-01000075815-4

182. Brd-k41256143-001-12-7

183. (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one

184. Androst-5-en-17-one, 3-hydroxy-, (3beta)- (9ci)

185. Z2213891300

186. 1a9d2040-240c-427d-ade4-0cb700b785cb

187. Prasterone (dhea; Dehydroepiandrosterone) 1.0 Mg/ml In Acetonitrile

188. (3s,8r,10r,13s)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

189. 105597-37-3

190. Dehydroepiandrosterone (dhea) 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	C₁₉H₂₈O₂
Molecular Weight	288.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	288.208930132 g/mol
Monoisotopic Mass	288.208930132 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	508
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	INTRAROSA
Active Ingredient	PRASTERONE
Company	AMAG PHARMS INC (Application Number: N208470. Patents: 8268806, 8629129, 8957054)

4.2 Drug Indication

DHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older peoples skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial age spots in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids). DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.

Intrarosa is indicated for the treatment of vulvar and vaginal atrophy in postmenopausal women having moderate to severe symptoms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

DHEA is naturally produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage); then another enzyme, CYP17A1, converts pregnenolone to 17-Hydroxypregnenolone and then to DHEA. DHEA is increased by exercise and calorie restriction. Some theorize that the increase in endogenous DHEA brought about by calorie restriction is partially responsible for the longer life expectancy known to be associated with calorie restriction.

5.2 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

5.3 ATC Code

G03XX01

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AA - Androstan derivatives

A14AA07 - Prasterone

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03X - Other sex hormones and modulators of the genital system

G03XX - Other sex hormones and modulators of the genital system

G03XX01 - Prasterone

5.4 Absorption, Distribution and Excretion

Absorption

Following a 50-mg DHEA PO dose in cynomolgus monkeys, systemic availability was only 3.1 +/- 0.4%. [PMID: 12970301]

5.5 Metabolism/Metabolites

Hepatic. As shown by their high conversion ratios (in a study involving cynomolgus monkeys), the major circulating metabolites of DHEA are DHEA-S, androsterone glucuronide, and androstane-3 alpha,17 beta-diol-glucuronide. [PMID: 12970301]

Dehydroisoandrosterone has known human metabolites that include 3,16-Dihydroxyandrost-5-en-17-one, 3,7-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one, and Dehydroisoandrosterone 3-glucuronide.

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

5.6 Biological Half-Life

12 hours

5.7 Mechanism of Action

DHEA can be understood as a prohormone for the sex steroids. DHEAS may be viewed as buffer and reservoir. As most DHEA is produced by the zona reticularis of the adrenal cortex, it is argued that there is a role in the immune and stress response. DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia as it is produced nearly entirely by the adrenal glands. Women with polycystic ovary syndrome tend to have elevated levels of DHEAS.

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