Ouabain octahydrate
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MedKoo CAT#: 574836

CAS#: 11018-89-6

Description: Ouabain octahydrate is a steroid hormone that inhibits Na(+)/K(+) ATPase, regulates transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cyctic fibrosis transport receptor or cAMP-activated Cl- channel) genes, and also alters localization of MRP1.


Chemical Structure

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Ouabain octahydrate
CAS# 11018-89-6

Theoretical Analysis

MedKoo Cat#: 574836
Name: Ouabain octahydrate
CAS#: 11018-89-6
Chemical Formula: C29H60O20
Exact Mass: 728.37
Molecular Weight: 728.779
Elemental Analysis: C, 47.79; H, 8.30; O, 43.91

Price and Availability

Size Price Availability Quantity
250mg USD 225 2 Weeks
1g USD 425 2 Weeks
5g USD 995 2 Weeks
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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

Appearance: Solid powder

Purity: >98% (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

More Info:

Product Data:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 125.0 171.52
Water 10.0 13.72

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.

Recalculate based on batch purity %
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.

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