O3125
Sigma

Ouabain octahydrate

≥95% (HPLC), powder

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Synonym

1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside)

Acocantherine

G-Strophanthin

Molecular Formula

C₂₉H₄₄O₁₂ · 8H₂O

Molecular Weight

728.77

CAS Number

11018-89-6

Beilstein Registry Number

101712

MDL number

MFCD00003688

PubChem Substance ID

24278610

EG/EC Number

211-139-3

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Descriptions

Caution

Aqueous solutions can be autoclaved.

Biochem/physiol Actions

Cardiac glycoside, 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, also alters localization of MRP1. Ouabain resistance is associated with appearance of Na(+)/K(+) ATPase isoforms with low binding affinity.

Properties

assay

≥95% (HPLC)

form

powder

optical activity

[α]25/D −31 to −32.5° in H₂O(lit.)

total impurities

~8 mol/mol water

color

white

solubility

H₂O: 10 mg/mL cold

ethanol: 10 mg/mL

H₂O: 50 mg/mL hot

abs.

ε1mM/220 nm, H₂O 15.5

References

Reference

Lingrel, J.B., et al., Ligand binding sites of Na,K-ATPase. Acta Physiol. Scand. 643, 69-77, (1998)

Capella, L.S., et al. Biochim. Biophys. Acta 1526, 293-300, (2001) abstract

Baudouin-Legros, M., et al. Am. J. Physiol. Cell Physiol. 284, C620-C626, (2003) abstract

Doris, P.A., and Bagrov, A.Y., Endogenous sodium pump inhibitors and blood pressure regulation: an update on recent progress. Proc. Soc. Exp. Biol. Med. 218, 156-167, (1998) abstract

van Huysse, J.W., and Leenen, F.H., Role of endogenous brain "ouabain" in the sympathoexcitatory and pressor effects of sodium. Clin. Exp. Hypertens. 20, 657-667, (1998) abstract

McDougall, J.G., and Yates, N.A., Natriuresis and inhibition of Na⁺/K⁺-ATPase: modulation of response by physiological manipulation. Clin. Exp. Pharmacol. Physiol. (Suppl.) 25, S57-S60, (1998) abstract

Blaustein, M.P., et al., The cellular mechanism of action of cardiotonic steroids: a new hypothesis. Clin. Exp. Hypertens. 20, 691-703, (1998) abstract

Peng, M., et al., Partial inhibition of Na⁺/K⁺-ATPase by ouabain induces the Ca²⁺-dependent expressions of early-response genes in cardiac myocytes. J. Biol. Chem. 271, 10372-10378, (1996) abstract

Hamlyn, J.M., et al., Observations on the nature, biosynthesis, secretion and significance of endogenous ouabain. Clin. Exp. Hypertens. 20, 523-533, (1998) abstract

Veerasingham, S.J., and Leenen, F.H., Ouabain- and central sodium-induced hypertension depend on the ventral anteroventral third ventricle region. Am. J. Physiol. 276, H63-H70, (1999) abstract

Juhaszova, M., and Blaustein, M.P., Na⁺ pump low and high ouabain affinity α subunit isoforms are differently distributed in cells. Proc. Natl. Acad. Sci. USA 94, 1800-1805, (1997) abstract

Beilstein

Beil. 18,V,5,625

Safety

Hazard Codes

Risk Statements

23/25-33

Safety Statements

RIDADR

UN 1544 6.1/PG 1

WGK Germany

RTECS

RN3850000