calusterone

{{Short description|Chemical compound}}

{{Drugbox

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

| image = Calusterone.svg

| image_class = skin-invert-image

| width = 250px

| tradename = Methosarb, Riedemil

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| routes_of_administration = By mouth

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

| CAS_number = 17021-26-0

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| PubChem = 28204

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| DrugBank_Ref =

| DrugBank = DB01564

| ChemSpiderID_Ref =

| ChemSpiderID = 26239

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

| UNII = 0678G6Q58A

| KEGG = D03338

| ChEBI =

| ChEMBL = 455706

| synonyms = 7β,17α-Dimethyltestosterone; NSC-88536; U-22550

| 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-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = IVFYLRMMHVYGJH-PVPPCFLZSA-N

}}

Calusterone (INN, USAN) (brand names Methosarb, Riedemil; former developmental code names NSC-88536, U-22550), also known as 7β,17α-dimethyltestosterone, is an orally active anabolic-androgenic steroid (AAS) that is used as an antineoplastic agent.{{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 JM |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 is a 17α-alkylated AAS similar in structure to bolasterone (which is its 7α-isomer).

{{Androgen/anabolic steroid dosages for breast cancer}}

Calusterone 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.