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Topterone

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Topterone
Clinical data

Other names	WIN-17665; Propyltestosterone; 17α-Propyltestosterone; 17α-Propylandrost-4-en-17β-ol-3-one
Routes of administration	Topical
Identifiers
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
CAS Number	60607-35-4
PubChem CID	9797605
ChemSpider	39526
UNII	77WPB17ZK1
CompTox Dashboard (EPA)	DTXSID20209417
ECHA InfoCard	100.056.638
Chemical and physical data
Formula	C₂₂H₃₄O₂
Molar mass	330.512 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
InChI InChI=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 Key:LZSOOHLAZHOTHJ-GUCLMQHLSA-N

Topterone (INNTooltip International Nonproprietary Name, USANTooltip 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.^[1]^[2]^[3]^[4]^[5]^[6]

References[edit]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. ISBN 978-1-4757-2085-3.

^ Ferrari RA, Chakrabarty K, Beyler AL, Wiland J (November 1978). "Suppression of sebaceous gland development in laboratory animals by 17alpha-propyltestosterone". The Journal of Investigative Dermatology. 71 (5): 320–323. doi:10.1111/1523-1747.ep12529809. PMID 712108.

^ Rasmusson GH (1986). "Chapter 18. Chemical Control of Androgen Action". Annual Reports in Medicinal Chemistry. Vol. 21. Academic Press. pp. 179–188 (183). doi:10.1016/S0065-7743(08)61128-8. ISBN 978-0-08-058365-5.

^ Ferrari RA, Chakrabarty K, Creange JE, Beyler AL, Potts OG, Schane HP (April 1980). "Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals". Methods and Findings in Experimental and Clinical Pharmacology. 2 (2): 65–69. PMID 7339330.

^ Chakrabarty K, Ferrari RA, Dessingue OC, Beyler AL, Schane HP (January 1980). "Mechanism of action of 17 alpha-propyltestosterone in inhibiting hamster flank organ development". The Journal of Investigative Dermatology. 74 (1): 5–8. doi:10.1111/1523-1747.ep12514560. PMID 7351494.

^ Marsden JR, Shuster S (6 December 2012). "The Treatment of Acne". Pharmacology of the Skin II: Methods, Absorption, Metabolism and Toxicity, Drugs and Diseases. Springer Science & Business Media. pp. 490–. ISBN 978-3-642-74054-1.