Epiandrosterone

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443728822

| IUPAC_name = (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,

| image = Epiandrosterone.svg

| image_class = skin-invert-image

| alt = Skeletal formula of epiandrosterone

| width = 200px

| image2 = Epiandrosterone-3D-balls.png

| alt2 = Ball-and-stick model of the epiandrosterone molecule

| width2 = 225

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 481-29-8

| ATC_prefix = none

| PubChem = 441302

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 390065

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8TR252Z538

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 541975

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 272195

| C=19 | H=30 | O=2

| smiles = O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@@H](O)CC[C@]34C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QGXBDMJGAMFCBF-LUJOEAJASA-N

}}

Epiandrosterone, or isoandrosterone,{{cite book| vauthors = Yalkowsky SH, He Y, Jain P |title=Handbook of Aqueous Solubility Data | edition = Second |url=https://books.google.com/books?id=cfFzJFthLCIC&pg=PA1209|date=19 April 2016|publisher=CRC Press|isbn=978-1-4398-0246-5|pages=1209–}}{{cite book | vauthors = Agarwal OP |title=Natural Products|url=https://books.google.com/books?id=Zb84fVthd_cC&pg=PA298|year=2006|publisher=Krishna Prakashan Media|isbn=978-81-87224-85-3|pages=298–}} also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.

Epiandrosterone has been shown to naturally occur in most mammals including pigs.{{cite journal | vauthors = Raeside JI, Renaud RL, Marshall DE | title = Identification of 5 alpha-androstane-3 beta,17 beta-diol and 3 beta-hydroxy-5 alpha-androstan-17-one sulfates as quantitatively significant secretory products of porcine Leydig cells and their presence in testicular venous blood | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 42 | issue = 1 | pages = 113–20 | date = March 1992 | pmid = 1558816 | doi = 10.1016/0960-0760(92)90017-d | s2cid = 53274020 }}

Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA.{{cite journal | vauthors = Callies F, Arlt W, Siekmann L, Hübler D, Bidlingmaier F, Allolio B | title = Influence of oral dehydroepiandrosterone (DHEA) on urinary steroid metabolites in males and females | journal = Steroids | volume = 65 | issue = 2 | pages = 98–102 | date = February 2000 | pmid = 10639021 | doi = 10.1016/s0039-128x(99)00090-2 | s2cid = 2630118 }}{{cite journal | vauthors = Labrie F, Cusan L, Gomez JL, Martel C, Bérubé R, Bélanger P, Chaussade V, Deloche C, Leclaire J | s2cid = 24975983 | display-authors = 6 | title = Changes in serum DHEA and eleven of its metabolites during 12-month percutaneous administration of DHEA | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 110 | issue = 1–2 | pages = 1–9 | date = May 2008 | pmid = 18359622 | doi = 10.1016/j.jsbmb.2008.02.003 }}{{cite thesis | vauthors = van de Kerkhof DH | title = Steroid profiling in doping analysis | degree = Ph.D. | publisher = University Utrecht | date = 2001 | hdl = 1874/328 }}{{cite journal | vauthors = Acacio BD, Stanczyk FZ, Mullin P, Saadat P, Jafarian N, Sokol RZ | title = Pharmacokinetics of dehydroepiandrosterone and its metabolites after long-term daily oral administration to healthy young men | journal = Fertility and Sterility | volume = 81 | issue = 3 | pages = 595–604 | date = March 2004 | pmid = 15037408 | doi = 10.1016/j.fertnstert.2003.07.035 | doi-access = free }}{{Verify source|date=October 2009}} Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.{{cite journal | vauthors = Huang XF, Luu-The V | title = Gene structure, chromosomal localization and analysis of 3-ketosteroid reductase activity of the human 3(alpha-->beta)-hydroxysteroid epimerase | journal = Biochimica et Biophysica Acta | volume = 1520 | issue = 2 | pages = 124–30 | date = August 2001 | pmid = 11513953 | doi = 10.1016/s0167-4781(01)00247-0 }}