Befiradol

Befiradol
(IUPAC) ime
	3-hloro-4-fluorofenil-[4-fluoro-4-([(5-metilpiridin-2-il)metilamino]metil)piperidin-1-il]metanon
Klinički podaci
Identifikatori
CAS broj	208110-64-9
ATC kod	nije dodeljen
PubChem	9865384
ChemSpider	8041076
UNII	RAT9OHA1YH
ChEMBL	CHEMBL45305
Hemijski podaci
Formula	C20H22ClF2N3O
Mol. masa	393.857 g/mol
SMILES	eMolekuli & PubHem
InChI
	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 ; Key: PKZXLMVXBZICTF-UHFFFAOYSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Nije kontrolisan

Befiradol (F-13,640) je veoma potentan i visoko selektivan pun agonist 5-HT_1A 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.^[5]^[6]^[7]^[8]^[9]^[10] Jedna SAR studija je pokazala da zamena dihalofenil grupe sa 3-benzotiofenilom povećava maksimalnu efikasnost od 84% na 124% (Ki=2.7 nM)^[11]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Bardin L, Tarayre JP, Malfetes N, Koek W, Colpaert FC (April 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. DOI:10.1159/000068404. PMID 12595749.
↑ Bruins Slot LA, Koek W, Tarayre JP, Colpaert FC (April 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. DOI:10.1016/S0014-2999(03)01566-8. PMID 12694810.
↑ Bardin L, Assié MB, Pélissou M, Royer-Urios I, Newman-Tancredi A, Ribet JP, Sautel F, Koek W, Colpaert FC. 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 |month=March |pmid=15528450 |doi=10.1124/jpet.104.077669 |url=}}
↑ Colpaert FC, Deseure K, Stinus L, Adriaensen H (February 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. DOI:10.1124/jpet.105.095109. PMID 16254131.
↑ Deseure K, Bréand S, Colpaert FC (July 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. DOI:10.1016/j.ejphar.2007.04.022. PMID 17512927.
↑ Bernard Vacher, Bernard Bonnaud, Wouter Koek. Pyridin-2-yl-methylamine derivatives, method of preparing and application as medicine. US Patent 6020345, May 21, 1999.
↑ Bollinger S, Hübner H, Heinemann FW, Meyer K, Gmeiner P (October 2010). „Novel pyridylmethylamines as highly selective 5-HT(1A) superagonists”. J. Med. Chem. 53 (19): 7167–79. DOI:10.1021/jm100835q. PMID 20860381.

Povezano

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid12595749-5] Bardin L, Tarayre JP, Malfetes N, Koek W, Colpaert FC (April 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. DOI:10.1159/000068404. PMID 12595749.

[pmid12694810-6] Bruins Slot LA, Koek W, Tarayre JP, Colpaert FC (April 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. DOI:10.1016/S0014-2999(03)01566-8. PMID 12694810.

[pmid15528450-7] Bardin L, Assié MB, Pélissou M, Royer-Urios I, Newman-Tancredi A, Ribet JP, Sautel F, Koek W, Colpaert FC. 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 |month=March |pmid=15528450 |doi=10.1124/jpet.104.077669 |url=}}

[pmid16254131-8] Colpaert FC, Deseure K, Stinus L, Adriaensen H (February 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. DOI:10.1124/jpet.105.095109. PMID 16254131.

[pmid17512927-9] Deseure K, Bréand S, Colpaert FC (July 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. DOI:10.1016/j.ejphar.2007.04.022. PMID 17512927.

[10] Bernard Vacher, Bernard Bonnaud, Wouter Koek. Pyridin-2-yl-methylamine derivatives, method of preparing and application as medicine. US Patent 6020345, May 21, 1999.

[11] Bollinger S, Hübner H, Heinemann FW, Meyer K, Gmeiner P (October 2010). „Novel pyridylmethylamines as highly selective 5-HT(1A) superagonists”. J. Med. Chem. 53 (19): 7167–79. DOI:10.1021/jm100835q. PMID 20860381.

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