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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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M B Pamnani et al.
Hypertension (Dallas, Tex. : 1979), 18(3), 316-324 (1991-09-11)
Reports from several laboratories suggest the presence of an ouabainlike compound in plasma and various animal tissues, particularly during acute volume expansion and in low-renin hypertension. It has been hypothesized that this compound, through inhibition of the Na(+)-K+ pump, can
T L Chan et al.
The Canadian journal of cardiology, 3(4), 197-204 (1987-05-01)
The mechanism of cardiac oscillatory activity induced by digitalis was studied in the canine ventricular muscle. We determined the role of sarcoplasmic reticulum in the phenomenon of oscillatory afterpotential and mechanical aftercontractions. Additionally we wished to study the interaction between
Total synthesis of ouabagenin and ouabain.
Hongxing Zhang et al.
Angewandte Chemie (International ed. in English), 47(7), 1272-1275 (2008-01-10)
Maddi Sridhar Reddy et al.
Chemistry, an Asian journal, 4(5), 725-741 (2009-03-19)
A full account of the total synthesis of ouabagenin and ouabain is described. A highly stereocontrolled anionic cycloaddition for the rapid construction of the basic steroid skeleton is a pivotal conversion for the whole strategy. A careful study was needed
J F Templeton et al.
Journal of medicinal chemistry, 30(8), 1502-1505 (1987-08-01)
The synthesis of 14-hydroxy-14 beta-pregn-4-ene-3,20-dione (14 beta-hydroxyprogesterone) is described. This novel steroid is about 10 times more potent than progesterone and one-tenth as potent as ouabagenin in an [3H]ouabain radioligand binding assay and is the first in a series of
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