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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

Dehydroepiandrosterone
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

Dehydroepiandrosterone

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 Weight 288.4 g/mol
Molecular Formula C19H28O2
XLogP33.2
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 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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05-Jan-2021
19-Nov-2024
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ABOUT THIS PAGE

Dehydroepiandrosterone Manufacturers

A Dehydroepiandrosterone manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Dehydroepiandrosterone, including repackagers and relabelers. The FDA regulates Dehydroepiandrosterone manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Dehydroepiandrosterone API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Dehydroepiandrosterone manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Dehydroepiandrosterone Suppliers

A Dehydroepiandrosterone supplier is an individual or a company that provides Dehydroepiandrosterone active pharmaceutical ingredient (API) or Dehydroepiandrosterone finished formulations upon request. The Dehydroepiandrosterone suppliers may include Dehydroepiandrosterone API manufacturers, exporters, distributors and traders.

click here to find a list of Dehydroepiandrosterone suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Dehydroepiandrosterone USDMF

A Dehydroepiandrosterone DMF (Drug Master File) is a document detailing the whole manufacturing process of Dehydroepiandrosterone active pharmaceutical ingredient (API) in detail. Different forms of Dehydroepiandrosterone DMFs exist exist since differing nations have different regulations, such as Dehydroepiandrosterone USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Dehydroepiandrosterone DMF submitted to regulatory agencies in the US is known as a USDMF. Dehydroepiandrosterone USDMF includes data on Dehydroepiandrosterone's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Dehydroepiandrosterone USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Dehydroepiandrosterone suppliers with USDMF on PharmaCompass.

Dehydroepiandrosterone NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Dehydroepiandrosterone as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Dehydroepiandrosterone API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Dehydroepiandrosterone as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Dehydroepiandrosterone and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Dehydroepiandrosterone NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Dehydroepiandrosterone suppliers with NDC on PharmaCompass.

Dehydroepiandrosterone GMP

Dehydroepiandrosterone Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Dehydroepiandrosterone GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Dehydroepiandrosterone GMP manufacturer or Dehydroepiandrosterone GMP API supplier for your needs.

Dehydroepiandrosterone CoA

A Dehydroepiandrosterone CoA (Certificate of Analysis) is a formal document that attests to Dehydroepiandrosterone's compliance with Dehydroepiandrosterone specifications and serves as a tool for batch-level quality control.

Dehydroepiandrosterone CoA mostly includes findings from lab analyses of a specific batch. For each Dehydroepiandrosterone CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Dehydroepiandrosterone may be tested according to a variety of international standards, such as European Pharmacopoeia (Dehydroepiandrosterone EP), Dehydroepiandrosterone JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Dehydroepiandrosterone USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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