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SB-705498

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Chemical compound

Pharmaceutical compound

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
PubChemCID	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 theTRPV1 ion channel.^[1]^[2] It has been evaluated inclinical trials for the treatment ofrhinitis andchronic cough.^[3]^[4]^[5]

References

[edit]

^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.

TRP channel modulators

TRPA

Activators

Blockers

TRPC

Activators	Adhyperforin (St John's wort) Diacyl glycerol GSK1702934A Hyperforin (St John's wort) Substance P
Blockers	DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-Amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators	ADP-ribose BCTC Calcium (intracellular) CIM-0216 Cold Coolact P Cooling Agent 10 Eucalyptol (eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol (mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g.,stevioside) (Stevia rebaudiana) Sweettastants (e.g.,glucose,fructose,sucrose; indirectly) Thio-BCTC WS-12
Blockers	AMG-333 Capsazepine Clotrimazole DCDPC Elismetrep Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-Amylcinnamoyl)anthranilic acid Nicotine (tobacco) Niflumic acid Ononetin PF-05105679 RQ-00203078 Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO TRPM4-IN-5