Topterone

Topterone (INN, USAN) (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]

Topterone
Clinical data
Other namesWIN-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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.056.638
Chemical and physical data
FormulaC22H34O2
Molar mass330.512 g·mol−1
3D model (JSmol)
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

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1–. ISBN 978-1-4757-2085-3.
  2. Ferrari, Richard A; Chakrabarty, Krishna; Beyler, Arthur L; Wiland, Julius (1978). "Suppression of Sebaceous Gland Development in Laboratory Animals by 17α-Propyltestosterone". Journal of Investigative Dermatology. 71 (5): 320–323. doi:10.1111/1523-1747.ep12529809. ISSN 0022-202X. PMID 712108.
  3. Annual Reports in Medicinal Chemistry. Academic Press. 16 September 1986. pp. 183–. ISBN 978-0-08-058365-5.
  4. Ferrari RA, Chakrabarty K, Creange JE, Beyler AL, Potts OG, Schane HP (1980). "Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals". Methods Find Exp Clin Pharmacol. 2 (2): 65–9. PMID 7339330.
  5. Chakrabarty, Krishna; Ferrari, Richard A.; Dessingue, Oksana C.; Beyler, Arthur L.; Schane, H. Philip (1980). "Mechanism of Action of 17α-Propyltestosterone in Inhibiting Hamster Flank Organ Development". Journal of Investigative Dermatology. 74 (1): 5–8. doi:10.1111/1523-1747.ep12514560. ISSN 0022-202X. PMID 7351494.
  6. Pharmacology of the Skin II: Methods, Absorption, Metabolism and Toxicity, Drugs and Diseases. Springer Science & Business Media. 6 December 2012. pp. 490–. ISBN 978-3-642-74054-1.



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