RU-22930: Difference between revisions

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{{short description|Chemical compound}}
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| CAS_number = 63094-42-8
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| UNII = 99QTV3S3MG
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| ChemSpiderID = 8124041
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| synonyms = 5,6-Dihydro-2-methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-2''H''-1,2,4-oxadiazin-3-(4''H'')-one<ref name="US4684635">https://www.google.com/patents/US4684635</ref>
| synonyms = 5,6-Dihydro-2-methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-2''H''-1,2,4-oxadiazin-3-(4''H'')-one<ref name="US4684635">{{Cite web|url=https://www.google.com/patents/US4684635|title = Compositions and methods for inhibiting the action of androgens}}</ref>


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'''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.<ref name="pmid6205409">{{cite journal | vauthors = Tindall DJ, Chang CH, Lobl TJ, Cunningham GR | title = Androgen antagonists in androgen target tissues | journal = Pharmacol. Ther. | volume = 24 | issue = 3 | pages = 367–400 | year = 1984 | pmid = 6205409 | doi = 10.1016/0163-7258(84)90010-x| url = }}</ref><ref name="pmid10637363">{{cite journal | vauthors = Singh SM, Gauthier S, Labrie F | title = Androgen receptor antagonists (antiandrogens): structure-activity relationships | journal = Curr. Med. Chem. | volume = 7 | issue = 2 | pages = 211–47 | year = 2000 | pmid = 10637363 | doi = 10.2174/0929867003375371| url = }}</ref> It is a [[binding selectivity|selective]] [[receptor antagonist|antagonist]] of the [[androgen receptor]] and consequently has [[progonadotropic]] effects by increasing [[gonadotropin]] and [[testosterone]] levels via disinhibition of the [[hypothalamic-pituitary-gonadal axis]].<ref name="pmid6205409" /> Unlike flutamide and nilutamide, the drug is said to be short-acting and inactive by [[injection (medicine)|injection]], but it has been found to be active [[topical medication|topical]]ly in animals, and hence could be useful for the treatment of [[androgen-dependent condition|androgen-dependent]] [[skin condition]]s.<ref name="pmid6205409" /><ref name="Thomson1989">{{cite journal|last1=Thomson|first1=D. S.|title=Pharmacology of Anti-androgens in the Skin|volume=87 / 2|year=1989|pages=483–493|issn=0171-2004|doi=10.1007/978-3-642-74054-1_36}}</ref>
'''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.<ref name="pmid6205409">{{cite journal | vauthors = Tindall DJ, Chang CH, Lobl TJ, Cunningham GR | title = Androgen antagonists in androgen target tissues | journal = Pharmacol. Ther. | volume = 24 | issue = 3 | pages = 367–400 | year = 1984 | pmid = 6205409 | doi = 10.1016/0163-7258(84)90010-x}}</ref><ref name="pmid10637363">{{cite journal | vauthors = Singh SM, Gauthier S, Labrie F | title = Androgen receptor antagonists (antiandrogens): structure-activity relationships | journal = Curr. Med. Chem. | volume = 7 | issue = 2 | pages = 211–47 | year = 2000 | pmid = 10637363 | doi = 10.2174/0929867003375371}}</ref> It is a [[binding selectivity|selective]] [[receptor antagonist|antagonist]] of the [[androgen receptor]] and consequently has [[progonadotropic]] effects by increasing [[gonadotropin]] and [[testosterone]] levels via disinhibition of the [[hypothalamic-pituitary-gonadal axis]].<ref name="pmid6205409" /> Unlike flutamide and nilutamide, the drug is said to be short-acting and inactive by [[injection (medicine)|injection]], but it has been found to be active [[topical medication|topical]]ly in animals, and hence could be useful for the treatment of [[androgen-dependent condition|androgen-dependent]] [[skin condition]]s.<ref name="pmid6205409" /><ref name="Thomson1989">{{cite book|last1=Thomson|first1=D. S.|title=Pharmacology of the Skin II|chapter=Pharmacology of Anti-androgens in the Skin|series=Handbook of Experimental Pharmacology|volume=87 / 2|year=1989|pages=483–493|issn=0171-2004|doi=10.1007/978-3-642-74054-1_36|isbn=978-3-642-74056-5}}</ref>


==See also==
==See also==

Latest revision as of 18:27, 2 March 2022

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
  • 2-Methyl-4-[4-nitro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazinan-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H10F3N3O4
Molar mass305.213 g·mol−1
3D model (JSmol)
  • CN1OCCN(C1=O)C1=CC=C(C(=C1)C(F)(F)F)N(=O)=O
  • 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[edit]

References[edit]

  1. ^ "Compositions and methods for inhibiting the action of androgens".
  2. ^ a b c 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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