SB-705498

SB-705498
Identifiers
	IUPAC name 1-(2-bromophenyl)-3-[(3R)-1-[5-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]urea;
CAS Number	501951-42-4;
PubChem CID	9910486;
CompTox Dashboard (EPA)	DTXSID20198236 ;
Chemical and physical data
Formula	C17H16BrF3N4O
Molar mass	429.241 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(C[C@@H]1NC(=O)NC2=CC=CC=C2Br)C3=NC=C(C=C3)C(F)(F)F;
	InChI InChI=1S/C17H16BrF3N4O/c18-13-3-1-2-4-14(13)24-16(26)23-12-7-8-25(10-12)15-6-5-11(9-22-15)17(19,20)21/h1-6,9,12H,7-8,10H2,(H2,23,24,26)/t12-/m1/s1; Key:JYILLRHXRVTRSH-GFCCVEGCSA-N;

SB-705498 is a drug which acts as a potent and selective blocker of the TRPV1 ion channel.^[1]^[2] It has been evaluated in clinical trials for the treatment of rhinitis and chronic cough.^[3]^[4]^[5]

References

^ Rami HK, Thompson M, Stemp G, Fell S, Jerman JC, Stevens AJ, Smart D, Sargent B, Sanderson D, Randall AD, Gunthorpe MJ, Davis JB. Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3287-91. doi:10.1016/j.bmcl.2006.03.030 PMID 16580202
^ Gunthorpe MJ, Hannan SL, Smart D, Jerman JC, Arpino S, Smith GD, Brough S, Wright J, Egerton J, Lappin SC, Holland VA, Winborn K, Thompson M, Rami HK, Randall A, Davis JB. Characterization of SB-705498, a potent and selective vanilloid receptor-1 (VR1/TRPV1) antagonist that inhibits the capsaicin-, acid-, and heat-mediated activation of the receptor. J Pharmacol Exp Ther. 2007 Jun;321(3):1183-92. doi:10.1124/jpet.106.116657 PMID 17392405
^ Wong GY, Gavva NR. Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks. Brain Res Rev. 2009 Apr;60(1):267-77. doi:10.1016/j.brainresrev.2008.12.006 PMID 19150372
^ Bareille P, Murdoch RD, Denyer J, Bentley J, Smart K, Yarnall K, Zieglmayer P, Zieglmayer R, Lemell P, Horak F. The effects of a TRPV1 antagonist, SB-705498, in the treatment of seasonal allergic rhinitis. Int J Clin Pharmacol Ther. 2013 Jul;51(7):576-84. doi:10.5414/CP201890 PMID 23735181
^ Holland C, van Drunen C, Denyer J, Smart K, Segboer C, Terreehorst I, Newlands A, Beerahee M, Fokkens W, Tsitoura DC. Inhibition of capsaicin-driven nasal hyper-reactivity by SB-705498, a TRPV1 antagonist. Br J Clin Pharmacol. 2014 May;77(5):777-88. doi:10.1111/bcp.12219 PMID 23909699

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[1] Rami HK, Thompson M, Stemp G, Fell S, Jerman JC, Stevens AJ, Smart D, Sargent B, Sanderson D, Randall AD, Gunthorpe MJ, Davis JB. Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3287-91. doi:10.1016/j.bmcl.2006.03.030 PMID 16580202

[2] Gunthorpe MJ, Hannan SL, Smart D, Jerman JC, Arpino S, Smith GD, Brough S, Wright J, Egerton J, Lappin SC, Holland VA, Winborn K, Thompson M, Rami HK, Randall A, Davis JB. Characterization of SB-705498, a potent and selective vanilloid receptor-1 (VR1/TRPV1) antagonist that inhibits the capsaicin-, acid-, and heat-mediated activation of the receptor. J Pharmacol Exp Ther. 2007 Jun;321(3):1183-92. doi:10.1124/jpet.106.116657 PMID 17392405

[3] Wong GY, Gavva NR. Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks. Brain Res Rev. 2009 Apr;60(1):267-77. doi:10.1016/j.brainresrev.2008.12.006 PMID 19150372

[4] Bareille P, Murdoch RD, Denyer J, Bentley J, Smart K, Yarnall K, Zieglmayer P, Zieglmayer R, Lemell P, Horak F. The effects of a TRPV1 antagonist, SB-705498, in the treatment of seasonal allergic rhinitis. Int J Clin Pharmacol Ther. 2013 Jul;51(7):576-84. doi:10.5414/CP201890 PMID 23735181

[5] Holland C, van Drunen C, Denyer J, Smart K, Segboer C, Terreehorst I, Newlands A, Beerahee M, Fokkens W, Tsitoura DC. Inhibition of capsaicin-driven nasal hyper-reactivity by SB-705498, a TRPV1 antagonist. Br J Clin Pharmacol. 2014 May;77(5):777-88. doi:10.1111/bcp.12219 PMID 23909699

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See also

References