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Ouabain (Ouabain Octahydrate; Acocantherine; G-Strophanthin; Strodival; NSC-25485; NSC25485) is a novel, potent and selective Na+/K+, -ATPase inhibitor with the potential to treat heart failure due to myocardial infarction. It binds to α2 /α3 subunit with Ki of 41 nM/15 nM. Ouabain (100 nM) inhibits ATPase activities with 25%. Ouabain (0.1 μM-1.0 μM) inhibits the Na+ pump and increases stored Ca2+ in cultured rat astrocytes. High Ouabain affinity isoforms are confined to a reticular distribution within the PM that paralleled underlying endoplasmic or sarcoplasmic reticulum.
Physicochemical Properties
| Molecular Formula | C29H44O12.8H2O | |
| Molecular Weight | 728.77 | |
| Exact Mass | 584.283 | |
| CAS # | 11018-89-6 | |
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| PubChem CID | 6364534 | |
| Appearance | White to off-white solid powder | |
| Density | 1.5±0.1 g/cm3 | |
| Boiling Point | 838.2±65.0 °C at 760 mmHg | |
| Melting Point | 260ºC | |
| Flash Point | 272.9±27.8 °C | |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C | |
| Index of Refraction | 1.655 | |
| LogP | -1.64 | |
| Hydrogen Bond Donor Count | 16 | |
| Hydrogen Bond Acceptor Count | 20 | |
| Rotatable Bond Count | 4 | |
| Heavy Atom Count | 49 | |
| Complexity | 1080 | |
| Defined Atom Stereocenter Count | 15 | |
| SMILES | C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O.O.O.O.O.O.O.O.O |
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| InChi Key | LPMXVESGRSUGHW-KAPJGFEOSA-N | |
| InChi Code | InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15?,16+,17+,18+,19?,21+,22-,23+,24+,25-,26+,27?,28+,29-/m0/s1 | |
| Chemical Name | 3-(6-Deoxy-alpha-L-mannopyranosyloxy)-1,5,11a,14,19-pentahydroxycard-20(22)-enolide | |
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| 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 |
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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) |
Biological Activity
| ln Vitro | Ouabain (100 μM) stimulates NLRP3 inflammasome activation and IL-1β release in macrophages. Ouabain-induced NLRP3 inflammasome activation is mediated through K+ efflux[1]. Ouabain (3 nM) affects the expression of EMT markers in NHK and ADPKD cells, and modifies cell-cell adhesion qualities in ADPKD. Moreover, ouabain promotes migration of ADPKD cells, selectively modulates tight junctions, and modulates adherens junctions in ADPKD cells in a selective manner. Ouabain also promotes TGFβ-Smad3 signaling, changes TER in ADPKD cells[2]. Ouabain (25, 50 or 100 nM) administration dramatically lowers cell proliferation and viability in Raji cells in a dose-dependent manner, with IC50 of 76.48±4.03 nM. Ouabain increases the frequency of apoptotic cells, activates autophagy, and upregulates Beclin -1 in Raji cells[4]. | ||
| ln Vivo | When mice are primed with LPS, ouabain (3 mg/kg) dramatically reduces heart contractile force with an increased LVESD. A lack of IL-1β reduces the damage and malfunction of the heart caused by ouabain. Ouabain-induced cardiac inflammation is partly attributed to the secretion of IL-1β by infiltrating macrophages. The effects of ouabain-induced cardiac dysfunction and macrophage infiltration are mitigated by NLRP3 and Casp1 deficiency[1]. Wistar rat thymocytes' ABCB1 activity is modulated by ouabain (30 µg/kg, ip), and Swiss mice's thymocytes respond similarly to 300 µg/kg of the drug. Rats treated with ouabain for 14 days show a substantial increase in MAP[3]. | ||
| Animal Protocol |
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| References |
[1]. The cardiac glycoside ouabain activates NLRP3 inflammasomes and promotes cardiac inflammation and dysfunction. PLoS One. 2017 May 11;12(5):e0176676. [2]. Ouabain promotes partial epithelial to mesenchymal transition (EMT) changes in human autosomal dominant polycystic kidney disease (ADPKD) cells. Exp Cell Res. 2017 Jun 15;355(2):142-152. [3]. Ouabain-induced alterations in ABCB1 of mesenteric lymph nodes and thymocytes of rats and mice. Oncol Lett. 2016 Dec;12(6):5275-5280. [4]. Ouabain induces apoptosis and autophagy in Burkitt's lymphoma Raji cells. Biomed Pharmacother. 2016 Dec;84:1841-1848. |
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| Additional Infomation |
Ouabain octahydrate is a cardenolide glycoside. A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE. |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.85 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 20.8 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: ≥ 2.08 mg/mL (2.85 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 20.8 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: ≥ 2.08 mg/mL (2.85 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 12.5 mg/mL (17.15 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3722 mL | 6.8609 mL | 13.7218 mL | |
| 5 mM | 0.2744 mL | 1.3722 mL | 2.7444 mL | |
| 10 mM | 0.1372 mL | 0.6861 mL | 1.3722 mL |