topterone

{{short description|Chemical compound}}

{{Drugbox

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

| image = Topterone.svg

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| routes_of_administration = Topical

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| CAS_number = 60607-35-4

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| PubChem = 9797605

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| ChemSpiderID = 39526

| UNII = 77WPB17ZK1

| synonyms = WIN-17665; Propyltestosterone; 17α-Propyltestosterone; 17α-Propylandrost-4-en-17β-ol-3-one

| C=22 | H=34 | O=2

| SMILES = CCCC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O

| StdInChI_Ref =

| StdInChI = 1S/C22H34O2/c1-4-10-22(24)13-9-19-17-6-5-15-14-16(23)7-11-20(15,2)18(17)8-12-21(19,22)3/h14,17-19,24H,4-13H2,1-3H3/t17-,18+,19+,20+,21+,22+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = LZSOOHLAZHOTHJ-GUCLMQHLSA-N

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Topterone ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (developmental code name WIN-17665), also known as 17α-propyltestosterone (or simply propyltestosterone) or as 17α-propylandrost-4-en-17β-ol-3-one, is a steroidal antiandrogen that was first reported in 1978 and was developed for topical administration but, due to poor effectiveness, 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=RA1-PA294|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1–}}{{cite journal | vauthors = Ferrari RA, Chakrabarty K, Beyler AL, Wiland J | title = Suppression of sebaceous gland development in laboratory animals by 17alpha-propyltestosterone | journal = The Journal of Investigative Dermatology | volume = 71 | issue = 5 | pages = 320–323 | date = November 1978 | pmid = 712108 | doi = 10.1111/1523-1747.ep12529809 | doi-access = free }}{{cite book | vauthors = Rasmusson GH | chapter =Chapter 18. Chemical Control of Androgen Action | title = Annual Reports in Medicinal Chemistry |date=1986 |volume=21 |pages=179–188 (183) |doi=10.1016/S0065-7743(08)61128-8 | chapter-url=https://books.google.com/books?id=qsFCGskRHZQC&pg=PA183 |publisher=Academic Press|isbn=978-0-08-058365-5}}{{cite journal | vauthors = Ferrari RA, Chakrabarty K, Creange JE, Beyler AL, Potts OG, Schane HP | title = Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 2 | issue = 2 | pages = 65–69 | date = April 1980 | pmid = 7339330 }}{{cite journal | vauthors = Chakrabarty K, Ferrari RA, Dessingue OC, Beyler AL, Schane HP | title = Mechanism of action of 17 alpha-propyltestosterone in inhibiting hamster flank organ development | journal = The Journal of Investigative Dermatology | volume = 74 | issue = 1 | pages = 5–8 | date = January 1980 | pmid = 7351494 | doi = 10.1111/1523-1747.ep12514560 | doi-access = free }}{{cite book | vauthors = Marsden JR, Shuster S | chapter = The Treatment of Acne |title=Pharmacology of the Skin II: Methods, Absorption, Metabolism and Toxicity, Drugs and Diseases| chapter-url= https://books.google.com/books?id=GvDxCAAAQBAJ&pg=PA490|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-74054-1|pages=490–}}