Synonym
SB-366791; SB 366791; SB366791.
IUPAC/Chemical Name
3-(4-chlorophenyl)-N-(3-methoxyphenyl)-2-propenamide
InChi Key
RYAMDQKWNKKFHD-JXMROGBWSA-N
InChi Code
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+
SMILES Code
O=C(NC1=CC=CC(OC)=C1)/C=C/C2=CC=C(Cl)C=C2
Purity
>98% (or refer to the Certificate of Analysis)
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.
Storage Condition
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, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
SB-366791 is a VR1/TRPV1 antagonist with an IC50 value of 5.7 nM.
In vitro activity:
In this study, inhibiting TRPV1 activity with SB-366791 significantly reduced Coxsackievirus B3 (CVB3) infection in induced-pluripotent stem cell-derived brain-like endothelial cells. SB-366791 could potentially limit viral entry into the brain, showcasing its potential as a treatment for neurotropic viruses.
Reference: Front Cell Infect Microbiol. 2023 Apr 17;13:1171275. https://pubmed.ncbi.nlm.nih.gov/37139492/
In vivo activity:
SB-366791 showed increased pain relief in both morphine-tolerant and non-tolerant mice without inducing genotoxic or mutagenic effects. SB-366791 led to an analgesic effect in the tail flick test. Behavioral results of the thermal nociception tests showed that SB-366791 had antinociceptive potential in both morphine-tolerant and non-tolerant mice without genotoxic or mutagenic effects.
Reference: Naunyn Schmiedebergs Arch Pharmacol. 2020 Mar;393(3):481-490. https://pubmed.ncbi.nlm.nih.gov/31655852/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
28.8 |
100.00 |
| Ethanol |
2.9 |
10.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
287.74
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Mamana J, Humber GM, Espinal ER, Seo S, Vollmuth N, Sin J, Kim BJ. Coxsackievirus B3 infects and disrupts human induced-pluripotent stem cell derived brain-like endothelial cells. Front Cell Infect Microbiol. 2023 Apr 17;13:1171275. doi: 10.3389/fcimb.2023.1171275. PMID: 37139492; PMCID: PMC10149843.
2. Rita Pereira EM, Souza JM, Carobin NV, Silva JF, Santos DC, Silva Júnior CA, Binda NS, Borges MH, Pinto Nagem RA, Kushmerick C, Ferreira J, Castro Junior CJ, Ribeiro FM, Gomez MV. Phoneutria toxin PnTx3-5 inhibits TRPV1 channel with antinociceptive action in an orofacial pain model. Neuropharmacology. 2020 Jan 1;162:107826. doi: 10.1016/j.neuropharm.2019.107826. Epub 2019 Oct 22. PMID: 31647972.
3. Mazeto TK, Picada JN, Correa ÁP, Rebelo IN, Ribeiro MT, Gomez MV, de Souza AH. Antinociceptive and genotoxic assessments of the antagonist TRPV1 receptor SB-366791 on morphine-induced tolerance in mice. Naunyn Schmiedebergs Arch Pharmacol. 2020 Mar;393(3):481-490. doi: 10.1007/s00210-019-01748-6. Epub 2019 Oct 26. PMID: 31655852.
4. 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. doi: 10.1016/j.ejphar.2006.04.046. Epub 2006 May 6. PMID: 16737693.
In vitro protocol:
1. Mamana J, Humber GM, Espinal ER, Seo S, Vollmuth N, Sin J, Kim BJ. Coxsackievirus B3 infects and disrupts human induced-pluripotent stem cell derived brain-like endothelial cells. Front Cell Infect Microbiol. 2023 Apr 17;13:1171275. doi: 10.3389/fcimb.2023.1171275. PMID: 37139492; PMCID: PMC10149843.
2. Rita Pereira EM, Souza JM, Carobin NV, Silva JF, Santos DC, Silva Júnior CA, Binda NS, Borges MH, Pinto Nagem RA, Kushmerick C, Ferreira J, Castro Junior CJ, Ribeiro FM, Gomez MV. Phoneutria toxin PnTx3-5 inhibits TRPV1 channel with antinociceptive action in an orofacial pain model. Neuropharmacology. 2020 Jan 1;162:107826. doi: 10.1016/j.neuropharm.2019.107826. Epub 2019 Oct 22. PMID: 31647972.
In vivo protocol:
1. Mazeto TK, Picada JN, Correa ÁP, Rebelo IN, Ribeiro MT, Gomez MV, de Souza AH. Antinociceptive and genotoxic assessments of the antagonist TRPV1 receptor SB-366791 on morphine-induced tolerance in mice. Naunyn Schmiedebergs Arch Pharmacol. 2020 Mar;393(3):481-490. doi: 10.1007/s00210-019-01748-6. Epub 2019 Oct 26. PMID: 31655852.
2. 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. doi: 10.1016/j.ejphar.2006.04.046. Epub 2006 May 6. PMID: 16737693.
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.
