Befiradol

Befiradol
IUPAC ime
3-​hloro-​4-​fluorofenil-​[4-​fluoro-​4-​([(5-​metilpiridin-​2-il)metilamino]metil)piperidin-​1-​il]metanon
Pravni status
Pravni status
  • Nije kontrolisan
Identifikatori
CAS broj208110-64-9 ДаY
ATC kodnone
PubChemCID 9865384
ChemSpider8041076 ДаY
UNIIRAT9OHA1YH ДаY
ChEMBLCHEMBL45305 ДаY
Hemijski podaci
FormulaC20H22ClF2N3O
Molarna masa393.857 g/mol
  • n2cc(C)ccc2CNCC(F)(CC3)CCN3C(=O)c(cc1Cl)ccc1F
  • InChI=1S/C20H22ClF2N3O/c1-14-2-4-16(25-11-14)12-24-13-20(23)6-8-26(9-7-20)19(27)15-3-5-18(22)17(21)10-15/h2-5,10-11,24H,6-9,12-13H2,1H3 ДаY
  • Key:PKZXLMVXBZICTF-UHFFFAOYSA-N ДаY

Befiradol (F-13,640) je veoma potentan i visoko selektivan pun agonist 5-HT1A receptora. On ima veoma moćno analgetsko i antialodinsko dejstvo koje je uporedivo sa visokim dozama opioidnih lekova protiv bolova, ali sa malobrojnijim i manje izraženim nuspojavama, kao i zanemarljivim razvojem tolerancije pri dužoj upotrebi.[1][2][3][4][5][6] Jedna SAR studija je pokazala da zamena dihalofenil grupe sa 3-benzotiofenilom povećava maksimalnu efikasnost od 84% na 124% (Ki=2.7 nM)[7]

Reference

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  1. ^ Bardin L, Tarayre JP, Malfetes N, Koek W, Colpaert FC (2003). „Profound, non-opioid analgesia produced by the high-efficacy 5-HT(1A) agonist F 13640 in the formalin model of tonic nociceptive pain”. Pharmacology. 67 (4): 182—94. PMID 12595749. doi:10.1159/000068404. 
  2. ^ Bruins Slot LA, Koek W, Tarayre JP, Colpaert FC (2003). „Tolerance and inverse tolerance to the hyperalgesic and analgesic actions, respectively, of the novel analgesic, F 13640”. European Journal of Pharmacology. 466 (3): 271—9. PMID 12694810. doi:10.1016/S0014-2999(03)01566-8. 
  3. ^ {{cite journal |vauthors=Bardin L, Assié MB, Pélissou M, Royer-Urios I, Newman-Tancredi A, Ribet JP, Sautel F, Koek W, Colpaert FC |title=Dual, hyperalgesic, and analgesic effects of the high-efficacy 5-hydroxytryptamine 1A (5-HT1A) agonist F 13640 [(3-chloro-4-fluoro-phenyl)-[4-fluoro-4-{[(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}piperidin-1-yl]methanone, fumaric acid salt]: relationship with 5-HT1A receptor occupancy and kinetic parameters |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=312 |issue=3 |pages=1034–42 |year=2005 |pmid=15528450 |doi=10.1124/jpet.104.077669 |url=}}
  4. ^ Colpaert FC, Deseure K, Stinus L, Adriaensen H (2006). „High-efficacy 5-hydroxytryptamine 1A receptor activation counteracts opioid hyperallodynia and affective conditioning”. The Journal of Pharmacology and Experimental Therapeutics. 316 (2): 892—9. PMID 16254131. doi:10.1124/jpet.105.095109. 
  5. ^ Deseure K, Bréand S, Colpaert FC (2007). „Curative-like analgesia in a neuropathic pain model: parametric analysis of the dose and the duration of treatment with a high-efficacy 5-HT(1A) receptor agonist”. European Journal of Pharmacology. 568 (1–3): 134—41. PMID 17512927. doi:10.1016/j.ejphar.2007.04.022. 
  6. ^ „Bernard Vacher, Bernard Bonnaud, Wouter Koek. Pyridin-2-yl-methylamine derivatives, method of preparing and application as medicine. US Patent 6020345, May 21, 1999.”. Архивирано из оригинала 31. 01. 2014. г. Приступљено 06. 10. 2012. 
  7. ^ Bollinger S, Hübner H, Heinemann FW, Meyer K, Gmeiner P (2010). „Novel pyridylmethylamines as highly selective 5-HT(1A) superagonists”. J. Med. Chem. 53 (19): 7167—79. PMID 20860381. doi:10.1021/jm100835q. 

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