oxymesterone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 444403776

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

| image = Oxymesterone.png

| image_class = skin-invert-image

| width = 225px

| tradename = Anamidol, Balnimax, Oranabol, Sanaboral, Theranabol, Tubil

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| legal_BR = C5

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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| routes_of_administration = By mouth

| bioavailability =

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

| CAS_number = 145-12-0

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| PubChem = 72061

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 65047

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

| UNII = 4R73K9MRMX

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C14665

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1908006

| synonyms = Oxymestrone; Ossimesterone; Methandrostenediolone; 4-Hydroxy-17α-methyltestosterone; 17α-Methylandrost-4-en-4,17β-diol-3-one; 4,17β-Dihydroxy-17α-methylandrost-4-en-3-one

| C=20 | H=30 | O=3

| SMILES = C[C@]12CCC(=O)C(=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RXXBBHGCAXVBES-XMUHMHRVSA-N

}}

Oxymesterone ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}) (brand names Anamidol, Balnimax, Oranabol, Sanaboral, Theranabol, Tubil), also known as methandrostenediolone, as well as 4-hydroxy-17α-methyltestosterone or 17α-methylandrost-4-en-4,17β-diol-3-one, is an orally active anabolic-androgenic steroid (AAS).{{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=PA923|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=923–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA778|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=778–}}{{cite web | url = https://www.drugs.com/international/oxymesterone.html | title = Oxymesterone | work = Drugs.com }}{{cite book| vauthors = Kochakian CD |title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA375|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=375–}} It was known by 1960.