RU-22930

RU-22930
Clinical data
Other names5,6-Dihydro-2-methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-2H-1,2,4-oxadiazin-3-(4H)-one[1]
Drug classNonsteroidal antiandrogen
Identifiers
IUPAC name
  • 2-Methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazinan-3-one
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H10F3N3O4
Molar mass305.213 g·mol−1
3D model (JSmol)
SMILES
  • CN1OCCN(C1=O)C1=CC=C(C(=C1)C(F)(F)F)N(=O)=O
InChI
  • InChI=1S/C11H10F3N3O4/c1-15-10(18)16(4-5-21-15)7-2-3-9(17(19)20)8(6-7)11(12,13)14/h2-3,6H,4-5H2,1H3
  • Key:SQAORNVRAYTOMS-UHFFFAOYSA-N

RU-22930 is a nonsteroidal antiandrogen (NSAA) related to the NSAAs flutamide and nilutamide (RU-23908) and was developed by Roussel Uclaf but was never marketed.[2][3] It is a selective antagonist of the androgen receptor and consequently has progonadotropic effects by increasing gonadotropin and testosterone levels via disinhibition of the hypothalamic-pituitary-gonadal axis.[2] Unlike flutamide and nilutamide, the drug is said to be short-acting and inactive by injection, but it has been found to be active topically in animals, and hence could be useful for the treatment of androgen-dependent skin conditions.[2][4]

See also

References

  1. ↑ "Compositions and methods for inhibiting the action of androgens".
  2. 1 2 3 Tindall DJ, Chang CH, Lobl TJ, Cunningham GR (1984). "Androgen antagonists in androgen target tissues". Pharmacol. Ther. 24 (3): 367–400. doi:10.1016/0163-7258(84)90010-x. PMID 6205409.
  3. ↑ Singh SM, Gauthier S, Labrie F (2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Curr. Med. Chem. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.
  4. ↑ Thomson, D. S. (1989). "Pharmacology of Anti-androgens in the Skin". Pharmacology of the Skin II. Handbook of Experimental Pharmacology. Vol. 87 / 2. pp. 483–493. doi:10.1007/978-3-642-74054-1_36. ISBN 978-3-642-74056-5. ISSN 0171-2004.



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