OUABAIN OCTAHYDRATE Chemical Properties

Melting point:

260 °C

storage temp. 

room temp

solubility 

H₂O: 10 mg/mL cold

form 

powder

color 

white

optical activity

[α]25/D 31 to 32.5° in H2O(lit.)

Water Solubility 

Soluble in water.

Sensitive 

Light Sensitive

BRN 

101712

Stability:

Stable for 2 years from date of purchase as supplied. Protect from exposure to moisture. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.

EPA Substance Registry System

Card-20(22)-enolide, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-, octahydrate, (1.beta.,3.beta.,5.beta.,11.alpha.)- (11018-89-6)

Safety Information

Hazard Codes 

T

Risk Statements 

23/25-33

Safety Statements 

45

RIDADR 

UN 1544 6.1/PG 1

WGK Germany 

3

RTECS 

RN3850000

F 

8

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29389090

MSDS

• Language:English Provider:ACROS

OUABAIN OCTAHYDRATE Usage And Synthesis

Description

Ouabain (11018-89-6) is a selective inhibitor of Na+ K+-ATPase isolated from Strophanthus gratus.1 Endogenous ouabain is found in human circulation.2 Displays cardiotonic and diuretic activity. May be used to induce hypertensive rat model.3?Cell permeable and active in vivo.

Chemical Properties

white to off-white crystalline powder

Chemical Properties

Ouabain is a white crystalline solid.

Uses

A cardiac glycoside that inhibits Na(+)/K(+) ATPase. It 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.

Uses

antiarrhythmic, cardiotonic, hypertensive, Na/K ATPase inhibitor

Uses

5HT2 receptor antagonist

Uses

Ouabain octahydrate, is used as a tool to induce in vivo excitotoxicity. Ouabain, as well as other endogenous digitalis-like compounds, can down-regulate the expression of 14-3-3 proteins in rat lens.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Biochem/physiol Actions

Ouabain has its specific binding site on integral proteins of the plasma membrane. Heart disease is treated using ouabain derivatives. Increased ouabain production is observed during exercise in humans. Abnormally high levels of ouabain are indicated in congestive heart failure and hypertension. Ouabain signalling affects intracellular calcium levels, which is known to activate nuclear factor κB (NFκB).

Potential Exposure

Ouabain, similar to digitoxin, is used to produce rapid digitalization in acute congestive heart failure. Also recommended in treatment of atrial or nodal paroxysmal tachycardia and atrial flutter; enzyme inhibitor.

Shipping

UN1544 Alkaloids, solid, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

It crystallises from water as the octahydrate. Dry it at 130o. It decomposes at 190o when dry. Store it in the dark as it is light sensitive, but it is stable in air. Its solubility (g/100mL) in H2O is 1.3 (~25o), 20 (~100o), and in EtOH it is 1.0 (~25o) and 12.5 (~78o). It is highly TOXIC as it is an inhibitor of cation transport and of Na+ and K+ ATPase. [Beilstein 18/5 V 625.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.).

References

1) Silva et al. (2012), New insights into the regulation of Na+,K(+)-ATPase by ouabain; Int. Rev. Cell. Mol. Biol., 294 99 2) Dvela et al. (2012), Endogenous ouabain regulates cell viability; Am. J. Physiol. Cell, Physiol., 302 C442

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