Ouabain
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| Ouabain
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| Systematic (IUPAC) name | |
| ? | |
| Identifiers | |
| CAS number | |
| ATC code | C01 |
| PubChem | |
| Chemical data | |
| Formula | C29H44O12 |
| Mol. mass | 584.652 |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
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Overview
Ouabain ('wa:ben, wa:'bein) is the familiar name of g-strophanthin, a poisonous cardiac glycoside.
Sources
Ouabain (g-strophanthin) is found in the ripe seeds of African plants Strophanthus gratus and Acokanthera ouabaio. k-strophanthin is found in the ripe seeds of Strophanthus kombé.
Function
Ouabain blocks the Na+/K+-ATPase in higher concentrations which are attainable in vitro or with intravenous dosage. This is the original use of ouabain; digoxin is a generally more popular compound used for similar indications (atrial fibrillation and congestive heart failure).
A recent concept is that at low concentrations ouabain in fact has the opposite effect, namely stimulation of the Na-K-ATPase.[1] This property is not exhibited by digoxin.[1]
Endogenous ouabain and ouabain mimics
In 1991 ouabain was identified as an endogenous hormone.[1] After some controversial results it is now probable that endogenous ouabain is an isomer of plant ouabain.[1] Ouabain is synthesized in the adrenal gland[1] and in the hypothalamus[1]. It is also produced in the heart, augmentedly in the condition of oxygen deficiency.[1]
Its exact mode of action and physiological significance is not yet determined. In normal human plasma, circulating levels ranging from 3 - 190 picoMol ouabain have been found, with higher levels in congestive heart failure, essential hypertension and some cancers. It has been suggested that these low concentrations of ouabain may stimulate the Na+/K+-ATPase while the higher levels achieved during intravenous therapy or in pathophysiological disorders may inhibit the NaK-pump.[1]
In the years following the discovery of ouabain in the human circulation, it was found in the adrenal glands of cows[1] and dogs.[1]
Uses
Ouabain is used worldwide extensively by scientists for in-vitro-studies to block the sodium pump (Na-K-ATPase). In many non rodent species, low concentrations of this substance (i.e., in the nanomolar range) provide effective stimulation of the NaK-pump. The issue in rodents is more complicated because there are different isoforms of the NaK-pump - some of which are very sensitive to ouabain while others are not. Ouabain is no longer widely used for the treatment of human heart failure. However, in France and Germany, intravenous ouabain has a long history in the treatment of heart failure, and some continue to advocate its use by mouth in angina pectoris and myocardial infarction. There is limited anecdotal evidence for improved efficacy of ouabain relative to digoxin in a small number of patients. However, no well controlled research exists that proves or disproves the efficacy this practice.
References
External links
- [3] Ouabainomics by Hamlyn
Cardiac glycosides (C01A) | |
|---|---|
| Digitalis glycosides | Acetyldigitoxin - Acetyldigoxin - Digitalis leaves - Digitoxin - Digoxin - Lanatoside C - Deslanoside - Metildigoxin - Gitoformate |
| Scilla glycosides | Proscillaridin |
| Strophantus glycosides | G-strophanthin - Cymarin |
| Other cardiac glycosides | Peruvoside |
fr:Strophanthine ja:ウアバイン nl:Ouabaïne
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
