SB 366791

Pricing Availability Delivery Time Qty
Cat.No. 1615 - SB 366791 | C16H14ClNO2 | CAS No. 472981-92-3
Description: Potent, selective, competitive TRPV1 antagonist
Chemical Name: 4'-Chloro-3-methoxycinnamanilide
Purity: ≥99% (HPLC)
Datasheet
Citations (14)
Reviews
Literature

Biological Activity

Potent, selective and competitive vanilloid TRPV1 receptor antagonist (pA2 = 7.71 at hVR1); antagonizes hTRPV1 receptors activated by agonists, noxious heat, but not protons. Displays selectivity over a wide range of receptors and systems including CB1 and CB2 receptors, voltage-gated Ca2+ channels and the hyperpolarization-activated current (Ih). Also available as part of the Vanilloid TRPV1 Receptor Tocriset™.

Licensing Information

Sold for research purposes under agreement from GlaxoSmithKline

Compound Libraries

SB 366791 is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 287.75
Formula C16H14ClNO2
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 472981-92-3
PubChem ID 667594
InChI Key RYAMDQKWNKKFHD-JXMROGBWSA-N
Smiles COC1=CC=CC(NC(=O)\C=C\C2=CC=C(Cl)C=C2)=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 28.77 100
ethanol 2.88 10

Preparing Stock Solutions

The following data is based on the product molecular weight 287.75. Batch specific molecular weights may vary from batch to batch due to solvent 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 3.48 mL 17.38 mL 34.75 mL
5 mM 0.7 mL 3.48 mL 6.95 mL
10 mM 0.35 mL 1.74 mL 3.48 mL
50 mM 0.07 mL 0.35 mL 0.7 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Fowler et al (2003) Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonylglycerol, and by a water soluble phosphate ester of anandamide: variability in response and involvement of arachidonic acid. Biochem.Pharmacol. 66 757 PMID: 12948856

Gavva et al (2005) Proton activation does not alter antagonist interaction with the capsaicin-binding pocket of TRPV1. Mol.Pharmacol. 68 1524 PMID: 16135784

Gunthorpe et al (2004) Identification and characterisation of SB-366791, a potent and selective vanilloid receptor (VR1/TRPV1) antagonist. Neuropharmacology 46 133 PMID: 14654105


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Keywords: SB 366791, supplier, Potent, selective, competitive, TRPV1, VR1, antagonists, Vanillioids, Receptors, TRPV, Channels, Transient, Receptor, Potential, SB366791, GlaxoSmithKline, GSK, TRPV, TRPV, Tocris Bioscience

14 Citations for SB 366791

Citations are publications that use Tocris products. Selected citations for SB 366791 include:

Yuan and Burrell (2010) Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor. J Neurophysiol 104 2766 PMID: 20884761

Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257 PMID: 15155534

Wang et al (2014) Innervation of enteric mast cells by primary spinal afferents in guinea pig and human small intestine. Am J Physiol Gastrointest Liver Physiol 307 G719 PMID: 25147231

Nguyen et al (2014) Transient receptor potential vanilloid type 1 channel may modulate opioid reward. Neuropsychopharmacology 39 2414 PMID: 24732880

Casarotto et al (2012) Opposing roles for cannabinoid receptor type-1 (CB1) and transient receptor potential vanilloid type-1 channel (TRPV1) on the modulation of panic-like responses in rats. Am J Physiol Renal Physiol 37 478 PMID: 21937980

Westlund et al (2010) Impact of central and peripheral TRPV1 and ROS levels on proinflammatory mediators and nociceptive behavior. J Biol Chem 6 46 PMID: 20691059

Gavva et al (2005) AMG 9810 [(E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties. J Pharmacol Exp Ther 313 474 PMID: 15615864

Alvarez-Berdugo et al (2014) Pharmacodynamics of TRPV1 agonists in a bioassay using human PC-3 cells. ScientificWorldJournal 2014 184526 PMID: 24688365

Ambrosino et al (2013) Activation and desensitization of TRPV1 channels in sensory neurons by the PPARα agonist palmitoylethanolamide. Br J Pharmacol 168 1430 PMID: 23083124

Schuelert et al (2010) Paradoxical effects of the cannabinoid CB2 receptor agonist GW405833 on rat osteoarthritic knee joint pain. Osteoarthritis Cartilage 18 1536 PMID: 20863899

Graham et al (2013) Epidermal keratinocyte polarity and motility require Ca2+ influx through TRPV1. J Cell Sci 126 4602 PMID: 23943873

Hazari et al (2011) TRPA1 and sympathetic activation contribute to increased risk of triggered cardiac arrhythmias in hypertensive rats exposed to diesel exhaust. Environ Health Perspect 119 951 PMID: 21377951

Li et al (2015) The Cancer Chemotherapeutic Paclitaxel Increases Human and Rodent Sensory Neuron Responses to TRPV1 by Activation of TLR4. J Neurosci 35 13487 PMID: 26424893

Shabir et al (2013) Functional expression of purinergic P2 receptors and transient receptor potential channels by the human urothelium. Mol Pain 305 F396 PMID: 23720349


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Literature in this Area

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