Synonym
Acocantherine, G-Strophanthin; Ouabain octahydrate
IUPAC/Chemical Name
4-((1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one octahydrate
InChi Key
TYBARJRCFHUHSN-DMJRSANLSA-N
InChi Code
InChI=1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1
SMILES Code
C[C@@H]1O[C@@H](O[C@@H]2C[C@@](O)(CC[C@]3([H])[C@]4([H])[C@H](O)C[C@@]5(C)[C@]3(O)CC[C@@H]5C6=CC(OC6)=O)[C@]4(CO)[C@H](O)C2)[C@H](O)[C@H](O)[C@H]1O.O.O.O.O.O.O.O.O
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ouabain Octahydrate is an inhibitor of Na+/K+-ATPase, used for the treatment of congestive heart failure.
In vitro activity:
This study determined whether physiological concentrations of ouabain induces EMT in human renal epithelial cells from patients with ADPKD. This study found that ADPKD cells respond to ouabain with a decrease in expression of the epithelial marker E-cadherin and increase in the expression of the mesenchymal markers N-cadherin, α smooth muscle actin (αSMA) and collagen-I; and the tight junction protein occludin and claudin-1. Other adhesion molecules, such as ZO-1, β-catenin and vinculin were not significantly modified by ouabain. At the cellular level, ouabain stimulated ADPKD cell migration, reduced cell-cell interaction, and the ability of ADPKD cells to form aggregates. Moreover, ouabain increased the transepithelial electrical resistance of ADPKD cell monolayers, suggesting that the paracellular transport pathway was preserved in the cells.
Reference: Exp Cell Res. 2017 Jun 15;355(2):142-152. https://pubmed.ncbi.nlm.nih.gov/28385574/
In vivo activity:
Therefore, the present study investigated alterations in the expression and activity of ABCB1 in the thymi, peripheral blood monocytes and lymph nodes of Wistar rats and Swiss mice treated acutely or chronically with ouabain. A decrease of almost 45% in the monocyte count and an increase of 55% in the basophil count were observed. A significant decrease (75% reduction) in the amount of cells with ABCB1 activity was found in the thymocytes of ouabain-treated rats and mice.
Reference: Oncol Lett. 2016 Dec;12(6):5275-5280. https://pubmed.ncbi.nlm.nih.gov/28105236/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
125.0 |
171.52 |
| Water |
10.0 |
13.72 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
728.78
Batch specific molecular weights may vary
from batch to batch
due to the degree 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 |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Venugopal J, McDermott J, Sanchez G, Sharma M, Barbosa L, Reif GA, Wallace DP, Blanco G. 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. doi: 10.1016/j.yexcr.2017.04.001. Epub 2017 Apr 3. PMID: 28385574; PMCID: PMC5497755.
2. Meng L, Wen Y, Zhou M, Li J, Wang T, Xu P, Ouyang J. Ouabain induces apoptosis and autophagy in Burkitt's lymphoma Raji cells. Biomed Pharmacother. 2016 Dec;84:1841-1848. doi: 10.1016/j.biopha.2016.10.114. Epub 2016 Nov 25. PMID: 27894666.
3. Kobayashi M, Usui-Kawanishi F, Karasawa T, Kimura H, Watanabe S, Mise N, Kayama F, Kasahara T, Hasebe N, Takahashi M. The cardiac glycoside ouabain activates NLRP3 inflammasomes and promotes cardiac inflammation and dysfunction. PLoS One. 2017 May 11;12(5):e0176676. doi: 10.1371/journal.pone.0176676. PMID: 28493895; PMCID: PMC5426608.
4. Lima DB, Valente RC, Capella MA. Ouabain-induced alterations in ABCB1 of mesenteric lymph nodes and thymocytes of rats and mice. Oncol Lett. 2016 Dec;12(6):5275-5280. doi: 10.3892/ol.2016.5366. Epub 2016 Nov 8. PMID: 28105236; PMCID: PMC5228555.
In vitro protocol:
1. Venugopal J, McDermott J, Sanchez G, Sharma M, Barbosa L, Reif GA, Wallace DP, Blanco G. 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. doi: 10.1016/j.yexcr.2017.04.001. Epub 2017 Apr 3. PMID: 28385574; PMCID: PMC5497755.
2. Meng L, Wen Y, Zhou M, Li J, Wang T, Xu P, Ouyang J. Ouabain induces apoptosis and autophagy in Burkitt's lymphoma Raji cells. Biomed Pharmacother. 2016 Dec;84:1841-1848. doi: 10.1016/j.biopha.2016.10.114. Epub 2016 Nov 25. PMID: 27894666.
In vivo protocol:
1. Kobayashi M, Usui-Kawanishi F, Karasawa T, Kimura H, Watanabe S, Mise N, Kayama F, Kasahara T, Hasebe N, Takahashi M. The cardiac glycoside ouabain activates NLRP3 inflammasomes and promotes cardiac inflammation and dysfunction. PLoS One. 2017 May 11;12(5):e0176676. doi: 10.1371/journal.pone.0176676. PMID: 28493895; PMCID: PMC5426608.
2. Lima DB, Valente RC, Capella MA. Ouabain-induced alterations in ABCB1 of mesenteric lymph nodes and thymocytes of rats and mice. Oncol Lett. 2016 Dec;12(6):5275-5280. doi: 10.3892/ol.2016.5366. Epub 2016 Nov 8. PMID: 28105236; PMCID: PMC5228555.
1: Younis W, Alamgeer, Schini-Kerth VB, Brentan da Silva D, Junior AG, Bukhari IA, Assiri AM. Role of the NO/cGMP pathway and renin-angiotensin system in the hypotensive and diuretic effects of aqueous soluble fraction from Crataegus songarica K. Koch. J Ethnopharmacol. 2020 Mar 1;249:112400. doi: 10.1016/j.jep.2019.112400. Epub 2019 Nov 16. PMID: 31739101.
2: Kitaguchi T, Moriyama Y, Taniguchi T, Maeda S, Ando H, Uda T, Otabe K, Oguchi M, Shimizu S, Saito H, Toratani A, Asayama M, Yamamoto W, Matsumoto E, Saji D, Ohnaka H, Miyamoto N. CSAHi study: Detection of drug-induced ion channel/receptor responses, QT prolongation, and arrhythmia using multi- electrode arrays in combination with human induced pluripotent stem cell-derived cardiomyocytes. J Pharmacol Toxicol Methods. 2017 May-Jun;85:73-81. doi: 10.1016/j.vascn.2017.02.001. Epub 2017 Feb 3. PMID: 28163191.
3: Aalders J, Ali S, de Jong TJ, Richardson MK. Assessing Teratogenicity from the Clustering of Abnormal Phenotypes in Individual Zebrafish Larvae. Zebrafish. 2016 Dec;13(6):511-522. doi: 10.1089/zeb.2016.1284. Epub 2016 Aug 25. PMID: 27560445.
4: Su CT, Hsu JT, Hsieh HP, Lin PH, Chen TC, Kao CL, Lee CN, Chang SY. Anti-HSV activity of digitoxin and its possible mechanisms. Antiviral Res. 2008 Jul;79(1):62-70. doi: 10.1016/j.antiviral.2008.01.156. Epub 2008 Feb 21. PMID: 18353452.
5: Carpentier RG, Sherief HT. Cocaine suppression of triggered activity. A possible mechanism of antiarrhythmic action. J Electrocardiol. 1994 Jan;27(1):35-9. doi: 10.1016/s0022-0736(05)80108-6. PMID: 8120476.
6: Forrest AB, Hawley JC, Malone MH. Testing for circadian differences in lethality for intravenous ouabain in male mice. J Ethnopharmacol. 1993 Aug;39(3):161-6. doi: 10.1016/0378-8741(93)90031-y. PMID: 8258972.
