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Merck
CN

O2627

Ouabagenin

≥95%

Synonym(s):

1β,3β,5,11α,14,19-Hexahydroxy-5β-card-20(22)-enolide, G-Strophanthidin

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About This Item

Empirical Formula (Hill Notation):
C23H34O8
CAS Number:
508-52-1
Molecular Weight:
438.51
UNSPSC Code:
12352200
PubChem Substance ID:
24897964
MDL number:
MFCD00057697

Key Documents

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InChI

1S/C23H34O8/c1-20-9-16(26)19-15(23(20,30)5-3-14(20)12-6-18(28)31-10-12)2-4-21(29)8-13(25)7-17(27)22(19,21)11-24/h6,13-17,19,24-27,29-30H,2-5,7-11H2,1H3/t13-,14+,15+,16+,17+,19+,20+,21-,22+,23-/m0/s1

SMILES string

[H][C@@]12CC[C@]3(O)C[C@@H](O)C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]4(C)[C@H](CC[C@]24O)C5=CC(=O)OC5

InChI key

BXSABLKMKAINIU-QOHCMMFCSA-N

assay

≥95%

storage temp.

2-8°C

General description

The aglycone of the cardiac glycoside ouabain.

Biochem/physiol Actions

Ouabagenin exerts cardiotonic effects through inhibition of Na+/K+-ATPase like the glycosides, albeit at significantly lower potency.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Inhalation - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
087H0592
044F0693

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A L Dorantes et al.
Archivos del Instituto de Cardiologia de Mexico, 64(6), 511-515 (1994-11-01)
It has been shown that, changes in the structure of the cardiac glycoside, are related to changes in their biological effects. In the present study we compared the effects of two structurally different digitalis compound (ouabain and ouabagenin), on K+
M Chatterjee et al.
Nuclear medicine and biology, 23(2), 115-120 (1996-02-01)
Two ouabagenin-cysteine conjugates were synthesized by condensing 3-beta monochloroacetyl and 3-beta, 11-alpha dichloroacetyl ouabagenin with cysteine. The resulting ligands were radiolabeled with technetium-99m (99mTc) to furnish a single homogenous 99mTc chelate in each case with good stability. The animal experiments
Rossen Radkov et al.
Biochemical and biophysical research communications, 356(1), 142-146 (2007-03-14)
Cardiac steroids inhibit Na,K-ATPase and the related non-gastric H,K-ATPase, while they do not interact with gastric H,K-ATPase. Introducing an arginine, the residue present in the gastric H,K-ATPase, in the second extracellular loop at the corresponding position 334 in the human
L K Lewis et al.
Hypertension (Dallas, Tex. : 1979), 24(5), 549-555 (1994-11-01)
An enzyme-linked immunosorbent assay is described for the measurement of ouabain in human plasma. This assay is specific for ouabain, strophanthidin, and ouabagenin, with other steroids, including digoxin and vasopressor hormones, exhibiting negligible cross-reactivity. Assay sensitivity was 0.06 nmol/L if
J N Gnabre et al.
General pharmacology, 24(5), 1107-1113 (1993-09-01)
1. Acetyltylophoroside (AcT) and tylogenin inhibit Na+/K(+)-ATPase in spite of having structures very different from cardiac glycosides (CGs). 2. Calculation of the lowest energy conformations of AcT and tylogenin and superpositions of these with the X-ray conformations of CGs and
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