oxabolone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = (8R,9S,10R,13S,14S,17S)-4,17-dihydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one

| image = Oxabolone.svg

| width =

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Intramuscular injection (as oxabolone cipionate)

| class = Androgen; Anabolic steroid

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 4721-69-1

| CAS_supplemental =

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

| UNII = 51RPF719WE

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem =

| IUPHAR_ligand =

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID_Ref =

| ChemSpiderID = 16736429

| KEGG =

| ChEBI =

| ChEMBL =

| synonyms = 4-Hydroxy-19-nortestosterone; 4,17β-Dihydroxyestr-4-en-3-one; 19-Norandrost-4-ene-4,17β-diol-3-one

| C=18 | H=26 | O=3

| SMILES = O=C4CC[C@H]3C(/CC[C@@H]1[C@@H]3CC[C@]2(C)[C@@H](O)CC[C@@H]12)=C4/O

| StdInChI_Ref =

| StdInChI = 1S/C18H26O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h10-12,14,16,20-21H,2-9H2,1H3/t10-,11-,12-,14+,16+,18+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = GXHBCWCMYVTJOW-YGRHGMIBSA-N

}}

Oxabolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed.{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA908|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=908–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA765|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=765–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA211|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=211–}} It can be formulated as the cipionate ester prodrug oxabolone cipionate, which, in contrast, has been marketed for medical use.

Oxabolone is on the World Anti-Doping Agency's list of prohibited substances,{{cite web | url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | title=The World Anti-Doping Code: The 2012 Prohibited List | publisher=World Anti-Doping Agency | access-date=2012-07-17 | url-status=dead | archive-url=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | archive-date=2012-05-13 }} and is therefore banned from use in most major sports.

The 17α-methylated analogue of oxabolone is methylhydroxynandrolone (4-hydroxy-17α-methyl-19-nortestosterone) and the 17α- and 19-methylated derivative of oxabolone is oxymesterone (4-hydroxy-17α-methyltestosterone).