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;
DrugBank	DB11883;
ChemSpider	8086137;
UNII	T74V9O0Y2W;
ChEMBL	ChEMBL207433;
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, et al. (June 2006). "Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development". Bioorganic & Medicinal Chemistry Letters. 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, et al. (June 2007). "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". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1183–92. doi:10.1124/jpet.106.116657. PMID 17392405. S2CID 6957155.
^ Wong GY, Gavva NR (April 2009). "Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks". Brain Research Reviews. 60 (1): 267–77. doi:10.1016/j.brainresrev.2008.12.006. PMID 19150372. S2CID 9951052.
^ Bareille P, Murdoch RD, Denyer J, Bentley J, Smart K, Yarnall K, et al. (July 2013). "The effects of a TRPV1 antagonist, SB-705498, in the treatment of seasonal allergic rhinitis". International Journal of Clinical Pharmacology and Therapeutics. 51 (7): 576–84. doi:10.5414/CP201890. PMID 23735181.
^ Holland C, van Drunen C, Denyer J, Smart K, Segboer C, Terreehorst I, et al. (May 2014). "Inhibition of capsaicin-driven nasal hyper-reactivity by SB-705498, a TRPV1 antagonist". British Journal of Clinical Pharmacology. 77 (5): 777–88. doi:10.1111/bcp.12219. PMC 4004398. PMID 23909699.

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[1] Rami HK, Thompson M, Stemp G, Fell S, Jerman JC, Stevens AJ, et al. (June 2006). "Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development". Bioorganic & Medicinal Chemistry Letters. 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, et al. (June 2007). "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". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1183–92. doi:10.1124/jpet.106.116657. PMID 17392405. S2CID 6957155.

[3] Wong GY, Gavva NR (April 2009). "Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks". Brain Research Reviews. 60 (1): 267–77. doi:10.1016/j.brainresrev.2008.12.006. PMID 19150372. S2CID 9951052.

[4] Bareille P, Murdoch RD, Denyer J, Bentley J, Smart K, Yarnall K, et al. (July 2013). "The effects of a TRPV1 antagonist, SB-705498, in the treatment of seasonal allergic rhinitis". International Journal of Clinical Pharmacology and Therapeutics. 51 (7): 576–84. doi:10.5414/CP201890. PMID 23735181.

[5] Holland C, van Drunen C, Denyer J, Smart K, Segboer C, Terreehorst I, et al. (May 2014). "Inhibition of capsaicin-driven nasal hyper-reactivity by SB-705498, a TRPV1 antagonist". British Journal of Clinical Pharmacology. 77 (5): 777–88. doi:10.1111/bcp.12219. PMC 4004398. PMID 23909699.

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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
DrugBank	DB11883
ChemSpider	8086137
UNII	T74V9O0Y2W
ChEMBL	ChEMBL207433
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

See also

References