:Androstanedione

{{Distinguish|androstanediol|androstenedione|androstenediol|androstadienol}}

{{Chembox

| ImageFile = 5alpha-Androstanedione.svg

| ImageSize = 225px

| ImageAlt =

| ImageClass = skin-invert-image

| IUPACName = (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione

| OtherNames = Dihydroandrostenedione; 5α-Androstanedione; 5α-Androstane-3,17-dione

| Section1 = {{Chembox Identifiers

| CASNo = 846-46-8

| ChEBI = 15994

| ChEMBL = 1230438

| ChemSpiderID = 193520

| DrugBank = DB01561

| PubChem = 222865

| SMILES = C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C

| StdInChI = 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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1

| StdInChIKey = RAJWOBJTTGJROA-WZNAKSSCSA-N

| UNII = 2KR72RNR8Z

}}

| Section2 = {{Chembox Properties

| C=19 | H=28 | O=2

| MolarMass = 288.431 g/mol

| Appearance =

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| Section3 = {{Chembox Hazards

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Androstanedione, also known as 5α-androstanedione or as 5α-androstane-3,17-dione, is a naturally occurring androstane (5α-androstane) steroid and an endogenous metabolite of androgens like testosterone, dihydrotestosterone (DHT), dehydroepiandrosterone (DHEA), and androstenedione.{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0000899|title=Human Metabolome Database: Showing metabocard for Androstanedione (HMDB0000899)}} It is the C5 epimer of etiocholanedione (5β-androstanedione). Androstanedione is formed from androstenedione by 5α-reductase and from DHT by 17β-hydroxysteroid dehydrogenase.{{cite book|author=Kenneth L. Becker|title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA994|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=994–}}{{cite book|author1=Eric S. Orwoll|author2=John P. Bilezikian|author3=Dirk Vanderschueren|title=Osteoporosis in Men: The Effects of Gender on Skeletal Health|url=https://books.google.com/books?id=nfWNYFdOsCsC&pg=PA296|date=30 November 2009|publisher=Academic Press|isbn=978-0-08-092346-8|pages=296–}} It has some androgenic activity.{{cite book|author=Charles D. Kochakian|title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA171|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=171–}}

In female genital skin, the conversion of androstenedione into DHT through 5α-androstanedione appears to be more important than the direct conversion of testosterone into DHT.{{cite journal | vauthors = Stanczyk FZ | title = Diagnosis of hyperandrogenism: biochemical criteria | journal = Best Pract Res Clin Endocrinol Metab | volume = 20 | issue = 2 | pages = 177–91 | date = June 2006 | pmid = 16772150 | doi = 10.1016/j.beem.2006.03.007 | url = }}