Inocoterone acetate

Inocoterone acetate (USAN) (developmental code names RU-38882, RU-882) is a steroid-like nonsteroidal antiandrogen (NSAA) that was developed for topical administration to treat acne but was never marketed.[1][2] It is the acetate ester of inocoterone, which is less potent in comparison.[3] Inocoterone acetate is actually not a silent antagonist of the androgen receptor but rather a weak partial agonist, similarly to steroidal antiandrogens like cyproterone acetate.[4]

Inocoterone acetate
Clinical data
Other namesRU-38882; RU-882; 2,5-Seco-A-dinorestr-9-en-17β-ol-5-one 17β-acetate
Drug classNonsteroidal antiandrogen
Identifiers
IUPAC name
  • [(3S,3aS,9aS,9bS)-6-Ethyl-3a-methyl-7-oxo-2,3,4,5,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalen-3-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H26O3
Molar mass290.403 g·mol−1
3D model (JSmol)
SMILES
  • CCC1=C2CC[C@]3([C@H]([C@@H]2CCC1=O)CC[C@@H]3OC(=O)C)C
InChI
  • InChI=1S/C18H26O3/c1-4-12-13-9-10-18(3)15(14(13)5-7-16(12)20)6-8-17(18)21-11(2)19/h14-15,17H,4-10H2,1-3H3/t14-,15+,17+,18+/m1/s1
  • Key:JDLUQDYTLSPFGS-FZCLSBEQSA-N

Inocoterone acetate was investigated for the treatment of acne but showed only modest (albeit statistically significant) efficacy in clinical trials.[2][5][6] A reduction of 26% of lesions was observed in males treated with the drug after 16 weeks (~3.7 months).[6][1] However, this is notably far less than that achieved with other agents such as benzoyl peroxide or antibiotics, which produce 50–75% reductions within 2 months.[1] Similar poor results with the topical route have disappointingly been found for other antiandrogens such as cyproterone acetate and spironolactone.[1] Similarly to rosterolone, inocoterone acetate has no systemic antiandrogenic activity when applied systemically.[7]

See also

References
  1. Richard A. Helms; David J. Quan (2006). Textbook of Therapeutics: Drug and Disease Management. Lippincott Williams & Wilkins. pp. 211–. ISBN 978-0-7817-5734-8.
  2. Bentham Science Publishers (September 1999). Current Pharmaceutical Design. Bentham Science Publishers. pp. 717–.
  3. Annual Reports in Medicinal Chemistry. Academic Press. 2 September 1987. pp. 203–. ISBN 978-0-08-058366-2.
  4. Térouanne B, Tahiri B, Georget V, Belon C, Poujol N, Avances C, Orio F, Balaguer P, Sultan C (2000). "A stable prostatic bioluminescent cell line to investigate androgen and antiandrogen effects". Mol. Cell. Endocrinol. 160 (1–2): 39–49. doi:10.1016/s0303-7207(99)00251-8. PMID 10715537. S2CID 13737435.
  5. Leo Plouffe, Jr; Botros R. M. B. Rizk (25 June 2015). Androgens in Gynecological Practice. Cambridge University Press. pp. 84–. ISBN 978-1-316-29887-9.
  6. Lookingbill, D. P. (1992). "Inocoterone and acne. The effect of a topical antiandrogen: results of a multicenter clinical trial". Archives of Dermatology. 128 (9): 1197–1200. doi:10.1001/archderm.128.9.1197. ISSN 0003-987X. PMID 1387778.
  7. Neumann, F.; Töpert, M. (1990). "Antiandrogens and Hair Growth: Basic Concepts and Experimental Research". Hair and Hair Diseases. pp. 791–826. doi:10.1007/978-3-642-74612-3_34. ISBN 978-3-642-74614-7.


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