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Funapide (TV-45070; XEN-402) is a novel and potent Sodium Channel Nav1.7 inhibitor, used as an analgesic agent for the treatment of a variety of chronic pain conditions, including osteoarthritis, neuropathic pain, postherpetic neuralgia, and erythromelalgia, as well as dental pain. Funapide acts as a small-molecule Nav1.7 and Nav1.8 voltage-gated sodium channel blocker.
Physicochemical Properties
| Molecular Formula | C22H14F3NO5 |
| Molecular Weight | 429.345 |
| Exact Mass | 429.082 |
| CAS # | 1259933-16-8 |
| Related CAS # | (R)-Funapide;1259933-15-7 |
| PubChem CID | 49836093 |
| Appearance | Off-white to light yellow solid powder |
| LogP | 4.317 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 31 |
| Complexity | 734 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | C1[C@]2(C3=CC=CC=C3N(C2=O)CC4=CC=C(O4)C(F)(F)F)C5=CC6=C(C=C5O1)OCO6 |
| InChi Key | NEBUOXBYNAHKFV-NRFANRHFSA-N |
| InChi Code | InChI=1S/C22H14F3NO5/c23-22(24,25)19-6-5-12(31-19)9-26-15-4-2-1-3-13(15)21(20(26)27)10-28-16-8-18-17(7-14(16)21)29-11-30-18/h1-8H,9-11H2/t21-/m0/s1 |
| Chemical Name | (3'S)-1'-{[5-(trifluoromethyl)furan-2-yl]methyl}-2H,6H-spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one |
| Synonyms | TV-45070 TV 45070 TV45070 XEN402 XEN-402 XEN 402 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1].Safety\nand Efficacy of a Topical Sodium Channel Inhibitor (TV-45070) in\nPatients With Postherpetic Neuralgia (PHN): A Randomized, Controlled,\nProof-of-Concept, Crossover Study, With a Subgroup Analysis of the\nNav1.7 R1150W Genotype. Clin J Pain. 2017 Apr;33(4):310-318. [2]. Recent progress\nin sodium channel modulators for pain. Bioorg Med Chem Lett. 2014 Aug\n15;24(16):3690-9. doi: 10.1016/j.bmcl.2014.06.038. Epub 2014 Jun 21. Review.\nPubMed PMID: 25060923. |
| Additional Infomation | Funapide has been used in trials studying the treatment of Pharmacokinetics, Postherpetic Neuralgia, and Osteoarthritis of the Knee. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~200 mg/mL (~465.82 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5.25 mg/mL (12.23 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 52.5 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: ≥ 5.25 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 52.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3291 mL | 11.6455 mL | 23.2910 mL | |
| 5 mM | 0.4658 mL | 2.3291 mL | 4.6582 mL | |
| 10 mM | 0.2329 mL | 1.1646 mL | 2.3291 mL |