Jump to content

RU-58841: Difference between revisions

Edit links
From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
update
update
Line 25: Line 25:
'''RU-58841''', also known as '''PSK-3841''' or '''HMR-3841''', is a [[nonsteroidal antiandrogen]] (NSAA) which was formerly under investigation by ProStrakan (previously ProSkelia and Strakan) for potential use as a [[topical medication|topical]] treatment for [[androgen-dependent condition]]s including [[acne]], [[pattern hair loss]], and excessive hair growth.<ref name="AdisInsight">[http://adisinsight.springer.com/drugs/800005990 PSK-3841 (HMR-3841, RU-58841) - AdisInsight]</ref><ref name="pmid8136306">{{cite journal | vauthors = Battmann T, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D | title = RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism | journal = J. Steroid Biochem. Mol. Biol. | volume = 48 | issue = 1 | pages = 55–60 | date = January 1994 | pmid = 8136306 | doi = 10.1016/0960-0760(94)90250-X | url = }}</ref><ref name="pmid15700772">{{cite journal | vauthors = Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, Blume-Peytavi U, Schäfer-Korting M | title = RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia | journal = Pharmazie | volume = 60 | issue = 1 | pages = 8–12 | date = January 2005 | pmid = 15700772 | doi = | url = http://www.ingentaconnect.com/content/govi/pharmaz/2005/00000060/00000001/art00002}}</ref> The compound is similar in structure to the NSAA [[RU-58642]] but contains a different [[side chain|side-chain]].<ref name="pmid11327585">{{cite journal | vauthors = Van Dort ME, Jung YW | title = Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 8 | pages = 1045–7 | date = April 2001 | pmid = 11327585 | doi = 10.1016/s0960-894x(01)00146-9 | url = }}</ref> These compounds are similar in [[chemical structure]] to [[nilutamide]],<ref name="pmid15757393">{{cite journal | vauthors = Poulos GA, Mirmirani P | title = Investigational medications in the treatment of alopecia | journal = Expert Opin Investig Drugs | volume = 14 | issue = 2 | pages = 177–84 | date = February 2005 | pmid = 15757393 | doi = 10.1517/13543784.14.2.177 | url = }}</ref> which is related to [[flutamide]], [[bicalutamide]], and [[enzalutamide]], all of which are NSAAs similarly.<ref name="ElancheranMaruthanila2015">{{cite journal|last1=Elancheran|first1=R.|last2=Maruthanila|first2=V. L.|last3=Ramanathan|first3=M.|last4=Kabilan|first4=S.|last5=Devi|first5=R.|last6=Kunnumakara|first6=A.|last7=Kotoky|first7=Jibon|title=Recent discoveries and developments of androgen receptor based therapy for prostate cancer|journal=MedChemComm|volume=6|issue=5|year=2015|pages=746–768|issn=2040-2503|doi=10.1039/C4MD00416G}}</ref> RU-58841 can be [[chemical synthesis|synthesized]] either by building the [[hydantoin]] [[moiety (chemistry)|moiety]] or by [[aryl group|aryl]] [[coupling reaction|coupling]] to 5,5-dimethylhydantoin.<ref name="LeonardLingham2014">{{cite journal|last1=Leonard|first1=Matthew J.|last2=Lingham|first2=Anthony R.|last3=Niere|first3=Julie O.|last4=Jackson|first4=Neale R. C.|last5=McKay|first5=Peter G.|last6=Hügel|first6=Helmut M.|title=Alternative synthesis of the anti-baldness compound RU58841|journal=RSC Adv.|volume=4|issue=27|year=2014|pages=14143–14148|issn=2046-2069|doi=10.1039/C4RA00332B}}</ref>
'''RU-58841''', also known as '''PSK-3841''' or '''HMR-3841''', is a [[nonsteroidal antiandrogen]] (NSAA) which was formerly under investigation by ProStrakan (previously ProSkelia and Strakan) for potential use as a [[topical medication|topical]] treatment for [[androgen-dependent condition]]s including [[acne]], [[pattern hair loss]], and excessive hair growth.<ref name="AdisInsight">[http://adisinsight.springer.com/drugs/800005990 PSK-3841 (HMR-3841, RU-58841) - AdisInsight]</ref><ref name="pmid8136306">{{cite journal | vauthors = Battmann T, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D | title = RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism | journal = J. Steroid Biochem. Mol. Biol. | volume = 48 | issue = 1 | pages = 55–60 | date = January 1994 | pmid = 8136306 | doi = 10.1016/0960-0760(94)90250-X | url = }}</ref><ref name="pmid15700772">{{cite journal | vauthors = Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, Blume-Peytavi U, Schäfer-Korting M | title = RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia | journal = Pharmazie | volume = 60 | issue = 1 | pages = 8–12 | date = January 2005 | pmid = 15700772 | doi = | url = http://www.ingentaconnect.com/content/govi/pharmaz/2005/00000060/00000001/art00002}}</ref> The compound is similar in structure to the NSAA [[RU-58642]] but contains a different [[side chain|side-chain]].<ref name="pmid11327585">{{cite journal | vauthors = Van Dort ME, Jung YW | title = Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 8 | pages = 1045–7 | date = April 2001 | pmid = 11327585 | doi = 10.1016/s0960-894x(01)00146-9 | url = }}</ref> These compounds are similar in [[chemical structure]] to [[nilutamide]],<ref name="pmid15757393">{{cite journal | vauthors = Poulos GA, Mirmirani P | title = Investigational medications in the treatment of alopecia | journal = Expert Opin Investig Drugs | volume = 14 | issue = 2 | pages = 177–84 | date = February 2005 | pmid = 15757393 | doi = 10.1517/13543784.14.2.177 | url = }}</ref> which is related to [[flutamide]], [[bicalutamide]], and [[enzalutamide]], all of which are NSAAs similarly.<ref name="ElancheranMaruthanila2015">{{cite journal|last1=Elancheran|first1=R.|last2=Maruthanila|first2=V. L.|last3=Ramanathan|first3=M.|last4=Kabilan|first4=S.|last5=Devi|first5=R.|last6=Kunnumakara|first6=A.|last7=Kotoky|first7=Jibon|title=Recent discoveries and developments of androgen receptor based therapy for prostate cancer|journal=MedChemComm|volume=6|issue=5|year=2015|pages=746–768|issn=2040-2503|doi=10.1039/C4MD00416G}}</ref> RU-58841 can be [[chemical synthesis|synthesized]] either by building the [[hydantoin]] [[moiety (chemistry)|moiety]] or by [[aryl group|aryl]] [[coupling reaction|coupling]] to 5,5-dimethylhydantoin.<ref name="LeonardLingham2014">{{cite journal|last1=Leonard|first1=Matthew J.|last2=Lingham|first2=Anthony R.|last3=Niere|first3=Julie O.|last4=Jackson|first4=Neale R. C.|last5=McKay|first5=Peter G.|last6=Hügel|first6=Helmut M.|title=Alternative synthesis of the anti-baldness compound RU58841|journal=RSC Adv.|volume=4|issue=27|year=2014|pages=14143–14148|issn=2046-2069|doi=10.1039/C4RA00332B}}</ref>


RU-58841 produces [[cyanonilutamide]] (RU-56279) and RU-59416 as [[metabolite]]s in animals.<ref name="pmid7947350">{{cite journal | vauthors = Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D | title = Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite | journal = J. Steroid Biochem. Mol. Biol. | volume = 51 | issue = 1-2 | pages = 47–55 | date = October 1994 | pmid = 7947350 | doi = 10.1016/0960-0760(94)90114-7 | url = }}</ref> Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant [[antiandrogen]]ic activity in animals.<ref name="pmid7947350" /> RU-59416 has very low affinity for the androgen receptor.<ref name="pmid7947350" />
RU-58841 produces [[cyanonilutamide]] (RU-56279) and RU-59416 as [[metabolite]]s in animals.<ref name="pmid7947350">{{cite journal | vauthors = Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D | title = Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite | journal = J. Steroid Biochem. Mol. Biol. | volume = 51 | issue = 1-2 | pages = 47–55 | date = October 1994 | pmid = 7947350 | doi = 10.1016/0960-0760(94)90114-7 | url = }}</ref> Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant [[antiandrogen]]ic activity in animals.<ref name="pmid7947350" /> RU-59416 has very low affinity for the androgen receptor.<ref name="pmid7947350" />

Find sources of Ru58841 here: [https://www.qualityru.com/default.asp www.Qualityru.com]




Revision as of 18:26, 15 January 2019

{{NOTOC}}: incorrect syntax, use {{subst:NOTOC}} or __NOTOC__ instead.

RU-58841
Clinical data
Other namesPSK-3841; HMR-3841
Drug classNonsteroidal antiandrogen Find Sources Of Ru58841 Here: https://www.ebay.com/itm/253997566197
Identifiers
  • 4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H18F3N3O3
Molar mass369.344 g·mol−1
3D model (JSmol)
  • CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C
  • InChI=1S/C17H18F3N3O3/c1-16(2)14(25)23(15(26)22(16)7-3-4-8-24)12-6-5-11(10-21)13(9-12)17(18,19)20/h5-6,9,24H,3-4,7-8H2,1-2H3
  • Key:ARBYGDBJECGMGA-UHFFFAOYSA-N

RU-58841, also known as PSK-3841 or HMR-3841, is a nonsteroidal antiandrogen (NSAA) which was formerly under investigation by ProStrakan (previously ProSkelia and Strakan) for potential use as a topical treatment for androgen-dependent conditions including acne, pattern hair loss, and excessive hair growth.[1][2][3] The compound is similar in structure to the NSAA RU-58642 but contains a different side-chain.[4] These compounds are similar in chemical structure to nilutamide,[5] which is related to flutamide, bicalutamide, and enzalutamide, all of which are NSAAs similarly.[6] RU-58841 can be synthesized either by building the hydantoin moiety or by aryl coupling to 5,5-dimethylhydantoin.[7]

RU-58841 produces cyanonilutamide (RU-56279) and RU-59416 as metabolites in animals.[8] Cyanonilutamide has relatively low affinity for the androgen receptor but shows significant antiandrogenic activity in animals.[8] RU-59416 has very low affinity for the androgen receptor.[8]



Template:Affinities of a selection of androgen receptor ligands at steroid hormone receptors

See also

References

  1. ^ PSK-3841 (HMR-3841, RU-58841) - AdisInsight
  2. ^ Battmann T, Bonfils A, Branche C, Humbert J, Goubet F, Teutsch G, Philibert D (January 1994). "RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism". J. Steroid Biochem. Mol. Biol. 48 (1): 55–60. doi:10.1016/0960-0760(94)90250-X. PMID 8136306.
  3. ^ Münster U, Nakamura C, Haberland A, Jores K, Mehnert W, Rummel S, Schaller M, Korting HC, Zouboulis C, Blume-Peytavi U, Schäfer-Korting M (January 2005). "RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia". Pharmazie. 60 (1): 8–12. PMID 15700772.
  4. ^ Van Dort ME, Jung YW (April 2001). "Synthesis and structure-activity studies of side-chain derivatized arylhydantoins for investigation as androgen receptor radioligands". Bioorg. Med. Chem. Lett. 11 (8): 1045–7. doi:10.1016/s0960-894x(01)00146-9. PMID 11327585.
  5. ^ Poulos GA, Mirmirani P (February 2005). "Investigational medications in the treatment of alopecia". Expert Opin Investig Drugs. 14 (2): 177–84. doi:10.1517/13543784.14.2.177. PMID 15757393.
  6. ^ Elancheran, R.; Maruthanila, V. L.; Ramanathan, M.; Kabilan, S.; Devi, R.; Kunnumakara, A.; Kotoky, Jibon (2015). "Recent discoveries and developments of androgen receptor based therapy for prostate cancer". MedChemComm. 6 (5): 746–768. doi:10.1039/C4MD00416G. ISSN 2040-2503.
  7. ^ Leonard, Matthew J.; Lingham, Anthony R.; Niere, Julie O.; Jackson, Neale R. C.; McKay, Peter G.; Hügel, Helmut M. (2014). "Alternative synthesis of the anti-baldness compound RU58841". RSC Adv. 4 (27): 14143–14148. doi:10.1039/C4RA00332B. ISSN 2046-2069.
  8. ^ a b c Cousty-Berlin D, Bergaud B, Bruyant MC, Battmann T, Branche C, Philibert D (October 1994). "Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite". J. Steroid Biochem. Mol. Biol. 51 (1–2): 47–55. doi:10.1016/0960-0760(94)90114-7. PMID 7947350.

Further reading


Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=RU-58841&oldid=878585432"