bolasterone

{{Short description|Chemical compound}}

{{Drugbox

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

| image = Bolasterone.png

| image_class = skin-invert-image

| width = 215px

| tradename = Myagen, Methosarb

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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 =

| protein_bound =

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

| CAS_number = 1605-89-6

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| PubChem = 102146

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| ChemSpiderID_Ref =

| ChemSpiderID = 92280

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

| UNII = T7ZM08F7FU

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| ChEMBL = 259548

| synonyms = U-19763; NSC-66233; 7α,17α-Dimethyltestosterone; 7α,17α-Dimethylandrost-4-en-17β-ol-3-one

| C=21 | H=32 | O=2

| SMILES = O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2[C@H](C)C3)C)(C)CC4

| StdInChI_Ref =

| StdInChI = 1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16+,17+,18-,19+,20+,21+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = IVFYLRMMHVYGJH-VLOLGRDOSA-N

}}

Bolasterone ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (brand names Myagen, Methosarb; former developmental code name U-19763), also known as 7α,17α-dimethyltestosterone, is a 17α-alkylated androgen/anabolic steroid (AAS) which is used in veterinary medicine.{{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=PA646|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=646–}}{{cite book| vauthors = Morton IK, Hall JS |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}} It has close structural similarity to testosterone, and like methyltestosterone has a methyl group at C17α in order to increase oral bioavailability. In addition, it is also 7α-methylated, similar to its 7β-methylated isomer calusterone. The medication has a low to moderate ratio of anabolic to androgenic activity, similar to that of fluoxymesterone.{{cite book| vauthors = Kochakian CD |title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA377|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=377, 401}}

Bolasterone 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.