5-Androstenedione

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (8R,9S,10R,13S,14S)-10,13-Dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione

| image = 5-Androstenedione.svg

| image_class = skin-invert-image

| width = 250

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| routes_of_administration = Oral

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 571-36-8

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| PubChem = 160531

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| DrugBank_Ref =

| DrugBank = DB01456

| ChemSpiderID_Ref =

| ChemSpiderID = 141063

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

| UNII = HEE11L5C3G

| KEGG =

| ChEBI = 83865

| ChEMBL = 1743203

| C=19 | H=26 | O=2

| SMILES = C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@]34C)[C@@H]1CCC2=O

| StdInChI = InChI=1S/C19H26O2/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/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

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

| StdInChIKey = SQGZFRITSMYKRH-QAGGRKNESA-N

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

| synonyms = Androst-5-ene-3,17-dione; Δ5-Androstenedione; NSC-12873

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5-Androstenedione, also known as androst-5-ene-3,17-dione, is a prohormone of testosterone. The World Anti-Doping Agency prohibits its use in athletes. In the United States, it is a controlled substance.

5-Androstenedione is structurally similar to 4-androstenedione, with the exception of the position of a carbon-carbon double bond.

4-Androstenedione is naturally produced in the body by the adrenal glands and gonads. In addition to testosterone, it is also a precursor of estrone and estradiol.{{cite journal | vauthors = Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS | display-authors = 6 | title = DrugBank 3.0: a comprehensive resource for 'omics' research on drugs | journal = Nucleic Acids Research | volume = 39 | issue = Database issue | pages = D1035–D1041 | date = January 2011 | pmid = 21059682 | pmc = 3013709 | doi = 10.1093/nar/gkq1126 }}{{cite journal | vauthors = Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M | display-authors = 6 | title = DrugBank: a knowledgebase for drugs, drug actions and drug targets | journal = Nucleic Acids Research | volume = 36 | issue = Database issue | pages = D901–D906 | date = January 2008 | pmid = 18048412 | pmc = 2238889 | doi = 10.1093/nar/gkm958 | author1-link = David S. Wishart }}

5-Androstenedione is on the World Anti-Doping Agency's list of prohibited substances,{{cite web|url=https://www.wada-ama.org/sites/default/files/wada_2020_english_prohibited_list_0.pdf|title=The World Anti-Doping Code: The 2020 Prohibited List|publisher=World Anti-Doping Agency|access-date=2019-12-28}} and is therefore banned from use in most major sports.

References

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