Ecabet Sodium (TA-2711; TA2711) is an eye drop used for the treatment of dry eye syndrome. It works by increasing the amount and quality of mucin made by corneal epithelia and conjunctival goblet cells. A glycoprotein called mucin, which is a part of the tear film, lubricates while delaying the loss of moisture from evaporating tears. Additionally, it is advertised in Japan as an oral agent for the management of gastritis and ulcers. Ecabet decreases the survival of H. pylori in the stomach and prevents pepsin activity in the gastric juice of experimental animals.
Physicochemical Properties
| Molecular Formula | C20H26NA2O5S |
| Molecular Weight | 424.46 |
| Exact Mass | 402.147 |
| Elemental Analysis | C, 56.59; H, 6.17; Na, 10.83; O, 18.85; S, 7.55 |
| CAS # | 86408-72-2 |
| Related CAS # | Ecabet;33159-27-2 |
| PubChem CID | 23663982 |
| Appearance | Solid powder |
| Density | 1.241 g/cm3 |
| Index of Refraction | 1.562 |
| LogP | 4.889 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 27 |
| Complexity | 672 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | C[C@]12CCC[C@@](C)(C(=O)O)[C@@H]1CCC1=CC(=C(C=C21)S(O)(=O)=O)C(C)C.[Na] |
| InChi Key | NQQLQPVASUVBKM-MUMAJMNHSA-L |
| InChi Code | InChI=1S/C20H28O5S.2Na/c1-12(2)14-10-13-6-7-17-19(3,8-5-9-20(17,4)18(21)22)15(13)11-16(14)26(23,24)25;;/h10-12,17H,5-9H2,1-4H3,(H,21,22)(H,23,24,25);;/q;2*+1/p-2/t17-,19-,20-;;/m1../s1 |
| Chemical Name | disodium;(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-6-sulfonato-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate |
| Synonyms | Ecabet Sodium; TA-2711; TA-2711E; TA-2711; TA 2711 |
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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
| Targets | ROS production; Bacterial; Apoptosis |
| References |
[1]. Efficacy and safety of ecabet sodium as an adjuvant therapy for Helicobacter pylori eradication: a systematic review and meta-analysis. Helicobacter. 2014 Oct;19(5):372-81. [2]. Ecabet sodium alleviates neomycin-induced hair cell damage. Free Radic Biol Med. 2015 Dec;89:1176-83. [3]. Ecabet sodium inhibits Helicobacter pylori lipopolysaccharide-induced activation of NADPH oxidase 1 or apoptosis of guinea pig gastric mucosal cells. Am J Physiol Gastrointest Liver Physiol. |
Solubility Data
| Solubility (In Vitro) |
DMSO: 80~100 mg/mL (198.8~248.5 mM) Ethanol: ~3 mg/mL (~7.5 mM) Water: ~16 mg/mL (~39.8 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.21 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 (6.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.21 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 25.0 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 | 2.3559 mL | 11.7797 mL | 23.5593 mL | |
| 5 mM | 0.4712 mL | 2.3559 mL | 4.7119 mL | |
| 10 mM | 0.2356 mL | 1.1780 mL | 2.3559 mL |