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Ouabain

Catalog No. DB01092 Name DrugBank
CAS Number 630-60-4 Website http://www.ualberta.ca/
M. F. C29H44O12 Telephone (780) 492-3111
M. W. 584.65246 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 963

SYNONYMS

IUPAC name
4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
IUPAC Traditional name
ouabain
Brand Name
Gratibain
Uabanin
Strophosan
Acocantherin
Astrobain
G-Strophicor
Kombetin
Purostrophan
Strophoperm
Uabaina
Gratus Strophanthin
Rectobaina
Solufantina
Strodival
Strophalen
Synonyms
Strophanthin G
Ouabain Octahydrate
Ouabaine
G-Strophanthin
Ouabagenin L-Rhamnoside
Strophanthin-G
Ouabain, Octahydrate

DATABASE IDS

PubChem CID 439501
PubChem SID 46505479
CAS Number 630-60-4

PROPERTIES

Hydrophobicity(logP) -1.2
Solubility 1.03E+004 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like digitalis. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-exchanging ATPase. [PubChem]
Indication For the treatment of atrial fibrillation and flutter and heart failure
Pharmacology Ouabain, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
Affected Organisms
Humans and other mammals
Protein Binding 60%
References
Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. [Pubmed]
Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. [Pubmed]
Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. [Pubmed]
Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. [Pubmed]
Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. Pubmed
  • Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. Pubmed
  • Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. Pubmed
  • Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. Pubmed
  • Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. Pubmed