Ouabain

CAS No:
630-60-4 Category:
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Product Details:

  • CAS No: 630-60-4
  • AHFC code:
  • Synonyms: G-Strophanthin Ouabagenin L-Rhamnoside Ouabain Octahydrate Ouabain, Octahydrate Ouabaine Strophanthin G Strophanthin-G
  • ATC Code: C01AC01
  • Chemical Formula: C15H12N2O2
  • Molecular Weight: 584.6525
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01092 (APRD00135)
  • SMILES: 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)C2=CC(=O)OC2)[C,H](O)[C,H](O)[C,H]1O
  • InChl: LPMXVESGRSUGHW-HBYQJFLCSA-N
  • PubChem: 4605
  • IUPAC: 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

Additional Details

Indication:
For the treatment of atrial fibrillation and flutter and heart failure
Pharmacodynamics:
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.
Mode of Action:
Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Metabolism:
Toxicity:
General Reference:
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
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