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Merck
CN

O3125

Ouabain octahydrate

From plant seeds (Strophantus gratus), ≥95% (HPLC), steroid hormone, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C29H44O12 · 8H2O
CAS Number:
11018-89-6
Molecular Weight:
728.77
NACRES:
NA.77
PubChem Substance ID:
24278610
UNSPSC Code:
12352200
EC Number:
211-139-3
MDL number:
MFCD00149240
Beilstein/REAXYS Number:
101712

Key Documents

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Product Name

Ouabain octahydrate, ≥95% (HPLC), powder

InChI key

TYBARJRCFHUHSN-DMJRSANLSA-N

InChI

1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1

SMILES string

O.O.O.O.O.O.O.O.C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O

biological source

plant seeds (Strophantus gratus)

assay

≥95% (HPLC)

form

powder

optical activity

[α]25/D −31 to −32.5° in H2O(lit.)

impurities

~8 mol/mol water

color

white

mp

260 °C

solubility

H2O: 10 mg/mL (cold)
ethanol: 10 mg/mL
H2O: 50 mg/mL (hot)

ε (extinction coefficient)

15.5 at 220 nm in H2O at 1 mM

storage temp.

room temp

Quality Level

200

Gene Information

human ... ATIC(471)
rat ... Atp1b1(25650)

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Application

Ouabain octahydrate has been used:
  • to determine the effect of salt and ammonia in the external environment on the rate of activity of Na+ /K+ in either silver or golden perch
  • in the basolateral compartment to induce maximal baseline short-circuit current in rat fetal distal lung epithelial (FDLE) cells
  • as an Na+/K+ ATPase inhibitor to study the relation between blister formation and adenosine triphosphate (ATP) dependent maintenance of plasma membrane homeostasis

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.
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).

Disclaimer

Aqueous solutions can be autoclaved.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

General description

Ouabain is a steroid hormone, naturally present in mammals.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 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

Regulatory Information

非剧毒-急性毒性1
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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0141
BCCN3412
BCCM1642
BCCJ7417
BCCH8909

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Male sex is associated with a reduced alveolar epithelial sodium transport
Kaltofen T, et al.
PLoS ONE, 10(8), e0136178-e0136178 (2015)
Gill ATPase activities of silver perch, Bidyanus bidyanus (Mitchell), and golden perch, Macquaria ambigua (Richardson): effects of environmental salt and ammonia
Alam Mostafa and Frankel Theresa L
Aquaculture (Amsterdam, Netherlands), 251(1), 118-133 (2006)
A fresh facet for ouabain action
Scheiner BG and Schoner W
Nature Medicine, 7(12), 1288-1288 (2001)
Ouabain, a steroid hormone that signals with slow calcium oscillations
Aizman O, et al.
Proceedings of the National Academy of Sciences of the USA, 98(23), 13420-13424 (2001)
Maria A Lim et al.
Frontiers in pharmacology, 8, 818-818 (2017-12-01)
Despite a broad spectrum of anti-arthritic drugs currently on the market, there is a constant demand to develop improved therapeutic agents. Efficient compound screening and rapid evaluation of treatment efficacy in animal models of rheumatoid arthritis (RA) can accelerate the
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