SB-366791
SB-366791 is a potent and selective TRPV1 antagonist. SB-366791 inhibits glutamatergic synaptic transmission in rat spinal dorsal horn following peripheral inflammation. SB-366791 decreased capsaicin-induced Ca2+ influx in cultured trigeminal ganglion cells in a concentration-dependent manner (0.5-10 microM) with an IC50 of 651.9 nM. SB366791 is a more selective and in vivo also a more potent TRPV1 receptor antagonist than capsazepine in the rat therefore, it may promote the assessment of the therapeutic utility of TRPV1 channel blockers.
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Chemical Information
| Name | SB-366791 |
|---|---|
| Iupac Chemical Name | 3-(4-chlorophenyl)-N-(3-methoxyphenyl)-2-propenamide |
| Synonyms | SB-366791; SB 366791; SB366791. |
| Molecular Formula | C16H14ClNO2 |
| Molecular Weight | 287.743 |
| Smile | O=C(NC1=CC=CC(OC)=C1)/C=C/C2=CC=C(Cl)C=C2 |
| InChiKey | RYAMDQKWNKKFHD-JXMROGBWSA-N |
| InChi | InChI=1S/C16H14ClNO2/c1-20-15-4-2-3-14(11-15)18-16(19)10-7-12-5-8-13(17)9-6-12/h2-11H,1H3,(H,18,19)/b10-7+ |
| CAS Number | 472981-92-3 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
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| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Lappin SC, Randall AD, Gunthorpe MJ, Morisset V. TRPV1 antagonist, SB-366791, inhibits glutamatergic synaptic transmission in rat spinal dorsal horn following peripheral inflammation. Eur J Pharmacol. 2006 Jul 1;540(1-3):73-81. Epub 2006 May 6. PubMed PMID: 16737693.
2: Gunthorpe MJ, Rami HK, Jerman JC, Smart D, Gill CH, Soffin EM, Luis Hannan S, Lappin SC, Egerton J, Smith GD, Worby A, Howett L, Owen D, Nasir S, Davies CH, Thompson M, Wyman PA, Randall AD, Davis JB. Identification and characterisation of SB-366791, a potent and selective vanilloid receptor (VR1/TRPV1) antagonist. Neuropharmacology. 2004 Jan;46(1):133-49. Erratum in: Neuropharmacology. 2004 May;46(6):905. PubMed PMID: 14654105.
3: van Veghel D, Cleynhens J, Pearce LV, Blumberg PM, Van Laere K, Verbruggen A, Bormans G. Synthesis and biological evaluation of [¹¹C]SB366791: a new PET-radioligand for in vivo imaging of the TRPV1 receptor. Nucl Med Biol. 2013 Jan;40(1):141-7. doi: 10.1016/j.nucmedbio.2012.08.011. Epub 2012 Nov 7. PubMed PMID: 23141549.
4: Niiyama Y, Kawamata T, Yamamoto J, Furuse S, Namiki A. SB366791, a TRPV1antagonist, potentiates analgesic effects of systemic morphine in a murine model of bone cancer pain. Br J Anaesth. 2009 Feb;102(2):251-8. doi: 10.1093/bja/aen347. Epub 2008 Nov 26. PubMed PMID: 19038965.
5: Varga A, Németh J, Szabó A, McDougall JJ, Zhang C, Elekes K, Pintér E, Szolcsányi J, Helyes Z. Effects of the novel TRPV1 receptor antagonist SB366791 in vitro and in vivo in the rat. Neurosci Lett. 2005 Sep 9;385(2):137-42. PubMed PMID: 15950380.
Chemical Structure
