:Penmesterol

{{short description|Chemical compound}}

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{{Infobox drug

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| IUPAC_name = (8R,9S,10R,13S,14S,17S)-3-Cyclopentyloxy-10,13,17-trimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-ol

| image = Penmesterol.svg

| image_class = skin-invert-image

| width = 250px

| tradename = Pandocrine; Testopan

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| routes_of_administration = By mouth

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| CAS_number_Ref =

| CAS_number = 67-81-2

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| PubChem = 20054971

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| ChemSpiderID = 16735903

| UNII = D5F29U03HM

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| ChEMBL = 2104849

| synonyms = RP-12222; 17α-Methyltestosterone 3-cyclopentyl enol ether

| C=25 | H=38 | O=2

| molecular_weight =

| SMILES = C[C@]12CCC(=CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C)OC5CCCC5

| StdInChI_Ref =

| StdInChI = 1S/C25H38O2/c1-23-13-10-19(27-18-6-4-5-7-18)16-17(23)8-9-20-21(23)11-14-24(2)22(20)12-15-25(24,3)26/h8,16,18,20-22,26H,4-7,9-15H2,1-3H3/t20-,21+,22+,23+,24+,25+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = ZUBDXGHKAAMAAA-RFXJPFPRSA-N

}}

Penmesterol ({{abbrlink|INN|International Nonproprietary Name}}) (brand names Pandrocine, Testopan; former developmental code name RP-12222), or penmestrol, also known as 17α-methyltestosterone 3-cyclopentyl enol ether,{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=1XBqAAAAMAAJ|date=4 October 2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2653}} is a synthetic, orally active anabolic-androgenic steroid (AAS) that was developed in the early 1960s.{{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=PA942|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=942–}}{{cite book| first = Ricardo | last = Azziz | name-list-style = vanc |title=Androgen Excess Disorders in Women|url=https://books.google.com/books?id=Ch-BsGAOtucC&pg=PA122|date=8 November 2007|publisher=Springer Science & Business Media|isbn=978-1-59745-179-6|pages=122–}}{{cite book| vauthors = Sittig M, ((William Andrew Publishing)) |title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA233|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2935–}}{{cite book| vauthors = List PH, Hörhammer L |title=Chemikalien und Drogen Teil A: N-Q|url=https://books.google.com/books?id=4TWnBgAAQBAJ&pg=PA504|date=12 March 2013|publisher=Springer-Verlag|isbn=978-3-642-65035-2|pages=504–}} It is the 3-cyclopentyl enol ether of methyltestosterone.{{Cite journal | vauthors = Ercoli A, Gardi R |title=Δ4-3-Keto Steroidal Enol Ethers. Paradoxical Dependency of Their Effectiveness on the Administration Route|journal=Journal of the American Chemical Society|volume=82|issue=3|pages=746–748|year=1960 |doi=10.1021/ja01488a062|bibcode=1960JAChS..82..746E }}{{cite book| vauthors = Wermuth CG |title=The Practice of Medicinal Chemistry|url=https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA731|date=2 May 2011|publisher=Academic Press|isbn=978-0-08-056877-5|pages=731–|author-link=Camille Georges Wermuth}}