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| 25mg |
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Purity: ≥98%
SB-366791 is a competitive and selective cinnamide TRPV1 (Vanilloid receptor 1) antagonist identified via high-throughput screening of a large chemical library. SB-366791 has IC50 of 5.7±1.2 nM. SB-366791 showed a concentration-dependent potentiation of pH 5-induced 45Ca2+uptake in CHO cells expressing rat TRPV1 but not in untransfected cells. In a FLIPR-based Ca(2+)-assay, SB-366791 produced a concentration-dependent inhibition of the response to capsaicin with an apparent pK(b) of 7.74 +/- 0.08. Schild analysis indicated a competitive mechanism of action with a pA2 of 7.71. In electrophysiological experiments, SB-366791 was demonstrated to be an effective antagonist of hTRPV1 when activated by different modalities, such as capsaicin, acid or noxious heat (50 degrees C). Unlike capsazepine, SB-366791 was also an effective antagonist vs. the acid-mediated activation of rTRPV1. In summary, SB-366791 is a new TRPV1 antagonist with high potency and an improved selectivity profile with respect to other commonly used TRPV1 antagonists. SB-366791 may therefore prove to be a useful tool to further study the biology of TRPV1.
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| ln Vivo |
The frequency of small excitatory postsynaptic currents (EPSCs) is inhibited by SB-366791 (30 μM). In the spinal cord slices of rats treated with FCA, the frequency of spontaneous EPSCs is decreased by SB-366791 (30 μM). EPSCs evoked by a C-fiber have their amplitude inhibited by SB-366791 (30 μM). Additionally, SB-366791 has been used in vivo to evaluate the possible analgesic effect of TRPV1 inhibition. It is known to significantly reduce capsaicin-induced hypothermia, eye wiping motions, and knee joint vasodilatation. By blocking glutamatergic transmission, SB-366791 appears to work through pre-synaptic mechanism(s)[1].
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| References |
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| Additional Infomation |
3-(4-chlorophenyl)-N-(3-methoxyphenyl)-2-propenamide is a member of cinnamamides and a secondary carboxamide.
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| Molecular Formula |
C₁₆H₁₄CLNO₂
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| Molecular Weight |
287.74
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| Exact Mass |
287.071
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| Elemental Analysis |
C, 66.79; H, 4.90; Cl, 12.32; N, 4.87; O, 11.12
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| CAS # |
472981-92-3
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| Related CAS # |
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| PubChem CID |
667594
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
494.2±45.0 °C at 760 mmHg
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| Melting Point |
169 °C
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| Flash Point |
252.7±28.7 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.650
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| LogP |
4.52
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
337
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C([H])=C([H])C(=C([H])C=1[H])/C(/[H])=C(\[H])/C(N([H])C1C([H])=C([H])C([H])=C(C=1[H])OC([H])([H])[H])=O
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| InChi Key |
RYAMDQKWNKKFHD-JXMROGBWSA-N
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| 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+
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| Chemical Name |
(E)-3-(4-chlorophenyl)-N-(3-methoxyphenyl)prop-2-enamide
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (8.69 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.69 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4754 mL | 17.3768 mL | 34.7536 mL | |
| 5 mM | 0.6951 mL | 3.4754 mL | 6.9507 mL | |
| 10 mM | 0.3475 mL | 1.7377 mL | 3.4754 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
 Structures of antagonists used in the study are shown in A. Comparison of antagonists for inhibition of capsaicin (0.5 μM) (B) and proton (pH 5) (C) induced activation of rat TRPV1.Mol Pharmacol.2005 Dec;68(6):1524-33. |
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 Concentration-dependent inhibition of capsaicin activation by mixtures of capsazepine and BCTC (A) or SB-366791 and BCTC (B) or capsazepine and ruthenium red (RR) (E).Mol Pharmacol.2005 Dec;68(6):1524-33. |
 A, concentration-response curves for BCTC inhibition of proton-induced45Ca2+uptake into CHO cells expressing rat TRPV1 in the absence or presence of 1, 3, or 10 μM capsazepine.Mol Pharmacol.2005 Dec;68(6):1524-33. |
 AMG0610 caused parallel rightward shifts in the inhibition curves of each of the group A antagonist.Mol Pharmacol.2005 Dec;68(6):1524-33. |
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 Models of agonist and antagonist interaction with capsaicin-binding pocket of rat TRPV1.Mol Pharmacol.2005 Dec;68(6):1524-33. |
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