Ouabain
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571527

CAS#: 630-60-4

Description: Ouabain is a cardiac steroid that binds to Na(+), K(+)-ATPase and inhibits its activity. Ouabain increases the force of contraction of heart muscle, stabilizes heart rate, and promotes the growth of cardiac, vascular, and neuronal cells both in vitro and in vivo.


Price and Availability

Size
Price

100mg
USD 230
Size
Price

Size
Price

Ouabain, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571527
Name: Ouabain
CAS#: 630-60-4
Chemical Formula: C29H44O12
Exact Mass: 584.2833
Molecular Weight: 584.66
Elemental Analysis: C, 59.58; H, 7.59; O, 32.84


Synonym: Ouabain; ; Acocantherin; Strodival; NSC 25485; NSC-25485; NSC25485

IUPAC/Chemical Name: 3-(6-Deoxy-alpha-L-mannopyranosyloxy)-1,5,11a,14,19-pentahydroxycard-20(22)-enolide

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

SMILES Code: O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CCC5(O)CC(O[C@H]6[C@@H]([C@@H]([C@H]([C@H](C)O6)O)O)O)CC(O)[C@]5(CO)[C@@]4([H])[C@H](O)C[C@]23C)=C1


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Fuerstenwerth H. On the differences between ouabain and digitalis glycosides. Am J Ther. 2014 Jan-Feb;21(1):35-42. doi: 10.1097/MJT.0b013e318217a609. Review. PubMed PMID: 21642827.

2: Yang YH, Wan Y, Lou H, Xue T, Su P. Relationship between ouabain and asthenozoospermia. J Huazhong Univ Sci Technolog Med Sci. 2014 Feb;34(1):87-90. doi: 10.1007/s11596-014-1236-x. Epub 2014 Feb 6. PubMed PMID: 24496684.

3: Dvela-Levitt M, Ami HC, Rosen H, Shohami E, Lichtstein D. Ouabain improves functional recovery following traumatic brain injury. J Neurotrauma. 2014 Dec 1;31(23):1942-7. doi: 10.1089/neu.2014.3544. Epub 2014 Oct 10. PubMed PMID: 25007121; PubMed Central PMCID: PMC4238276.

4: Ninsontia C, Chanvorachote P. Ouabain mediates integrin switch in human lung cancer cells. Anticancer Res. 2014 Oct;34(10):5495-502. PubMed PMID: 25275046.

5: Lewis LK, Yandle TG, Hilton PJ, Jensen BP, Begg EJ, Nicholls MG. Endogenous ouabain is not ouabain. Hypertension. 2014 Oct;64(4):680-3. doi: 10.1161/HYPERTENSIONAHA.114.03919. Epub 2014 Jul 7. Review. PubMed PMID: 25001271.

6: Ruanghirun T, Pongrakhananon V, Chanvorachote P. Ouabain enhances lung cancer cell detachment. Anticancer Res. 2014 May;34(5):2231-8. PubMed PMID: 24778025.

7: Rana S, Rajakumar A, Geahchan C, Salahuddin S, Cerdeira AS, Burke SD, George EM, Granger JP, Karumanchi SA. Ouabain inhibits placental sFlt1 production by repressing HSP27-dependent HIF-1α pathway. FASEB J. 2014 Oct;28(10):4324-34. doi: 10.1096/fj.14-252684. Epub 2014 Jun 26. PubMed PMID: 24970393; PubMed Central PMCID: PMC4202104.

8: Dvela M, Rosen H, Ben-Ami HC, Lichtstein D. Endogenous ouabain regulates cell viability. Am J Physiol Cell Physiol. 2012 Jan 15;302(2):C442-52. doi: 10.1152/ajpcell.00336.2011. Epub 2011 Oct 26. PubMed PMID: 22031604.

9: Penniyaynen VA, Kipenko AV, Lopatina EV, Krylov BV. Effect of ouabain on growth of skin explants in organotypic culture. Bull Exp Biol Med. 2013 Feb;154(4):419-20. English, Russian. PubMed PMID: 23486569.

10: Padilha AS, Salaices M, Vassallo DV, Batista PR, Siman FD. Hypertensive effects of the iv administration of picomoles of ouabain. Braz J Med Biol Res. 2011 Sep;44(9):933-8. Epub 2011 Aug 19. Review. PubMed PMID: 21956536.

11: Silva E, Soares-da-Silva P. New insights into the regulation of Na+,K+-ATPase by ouabain. Int Rev Cell Mol Biol. 2012;294:99-132. doi: 10.1016/B978-0-12-394305-7.00002-1. Review. PubMed PMID: 22364872.

12: Bai YL, Chu QJ, Li J, Chen YY, Li WJ, Zhang Q. A comparison of the effects of digoxin, ouabain and milrinone on naloxone-precipitated withdrawal syndrome in mice. Eur J Pharmacol. 2012 Nov 5;694(1-3):69-74. doi: 10.1016/j.ejphar.2012.08.004. Epub 2012 Aug 30. PubMed PMID: 22960325.

13: Gomez-Sanchez EP, Foecking MF, Sellers D, Blankenship MS, Gomez-Sanchez CE. Is the circulating ouabain-like compound ouabain? Am J Hypertens. 1994 Jul;7(7 Pt 1):647-50. PubMed PMID: 7946167.

14: Jaiswal MK, Dvela M, Lichtstein D, Mallick BN. Endogenous ouabain-like compounds in locus coeruleus modulate rapid eye movement sleep in rats. J Sleep Res. 2010 Mar;19(1 Pt 2):183-91. doi: 10.1111/j.1365-2869.2009.00781.x. Epub 2009 Oct 28. PubMed PMID: 19878449.

15: Kajimura S, Hirano T, Moriyama S, Vakkuri O, Leppäluoto J, Grau EG. Changes in plasma concentrations of immunoreactive ouabain in the tilapia in response to changing salinity: is ouabain a hormone in fish? Gen Comp Endocrinol. 2004 Jan 1;135(1):90-9. PubMed PMID: 14644648.

16: Kawamura A, Abrell LM, Maggiali F, Berova N, Nakanishi K, Labutti J, Magil S, Haupert GT Jr, Hamlyn JM. Biological implication of conformational flexibility in ouabain: observations with two ouabain phosphate isomers. Biochemistry. 2001 May 15;40(19):5835-44. PubMed PMID: 11341849.

17: Schweigert B, Lafaire AV, Schwarz W. Voltage dependence of the Na-K ATPase: measurements of ouabain-dependent membrane current and ouabain binding in oocytes of Xenopus laevis. Pflugers Arch. 1988 Oct;412(6):579-88. PubMed PMID: 2850533.

18: Vakkuri O, Arnason SS, Joensuu P, Jalonen J, Vuolteenaho O, Leppäluoto J. Radioiodinated tyrosyl-ouabain and measurement of a circulating ouabain-like compound. Clin Chem. 2001 Jan;47(1):95-101. PubMed PMID: 11148183.

19: Manunta P, Rogowski AC, Hamilton BP, Hamlyn JM. Ouabain-induced hypertension in the rat: relationships among plasma and tissue ouabain and blood pressure. J Hypertens. 1994 May;12(5):549-60. PubMed PMID: 7930555.

20: Di Bartolo V, Balzan S, Pieraccini L, Ghione S, Pegoraro S, Biver P, Revoltella R, Montali U. Evidence for an endogenous ouabain-like immunoreactive factor in human newborn plasma coeluted with ouabain on HPLC. Life Sci. 1995;57(15):1417-25. PubMed PMID: 7674832.