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Ouabain information


Ouabain
Clinical data
Trade namesStrodival
AHFS/Drugs.comInternational Drug Names
ATC code
  • C01AC01 (WHO)
Identifiers
IUPAC name
  • 1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside)
    OR
    4-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-
    (hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-
    pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-one
CAS Number
  • 630-60-4 checkY
PubChem CID
  • 439501
IUPHAR/BPS
  • 4826
DrugBank
  • DB01092 checkY
ChemSpider
  • 388599 checkY
UNII
  • 5ACL011P69
KEGG
  • C01443 checkY
ChEBI
  • CHEBI:472805 checkY
ChEMBL
  • ChEMBL222863 checkY
PDB ligand
  • OBN (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID0043765 Edit this at Wikidata
ECHA InfoCard100.010.128 Edit this at Wikidata
Chemical and physical data
FormulaC29H44O12
Molar mass584.659 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C\1OC/C(=C/1)[C@H]2CC[C@@]6(O)[C@]2(C)C[C@@H](O)[C@H]4[C@H]6CC[C@]5(O)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)C[C@@H](O)[C@]45CO
InChI
  • InChI=1S/C29H44O12/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/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1 checkY
  • Key:LPMXVESGRSUGHW-HBYQJFLCSA-N checkY
  (verify)

Ouabain /wɑːˈbɑːɪn/[1] or /ˈwɑːbn, ˈwæ-/ (from Somali waabaayo, "arrow poison" through French ouabaïo) also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium–potassium ion pump.[2] However, adaptations to the alpha-subunit of the Na+/K+-ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore- insect species, that have resulted in toxin resistance.[3]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[4]

  1. ^ "ouabain" in the World English Dictionary
  2. ^ Cite error: The named reference Pubchem was invoked but never defined (see the help page).
  3. ^ Dobler S, Dalla S, Wagschal V, Agrawal AA (August 2012). "Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase". Proceedings of the National Academy of Sciences of the United States of America. 109 (32): 13040–13045. doi:10.1073/pnas.1202111109. PMC 3420205. PMID 22826239.
  4. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.

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Ouabain

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Ouabain /wɑːˈbɑːɪn/ or /ˈwɑːbeɪn, ˈwæ-/ (from Somali waabaayo, "arrow poison" through French ouabaïo) also known as g-strophanthin, is a plant derived...

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Ventricular escape beat

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escape rate Ouabain infusion decreases ventricular escape time and increases ventricular escape rhythm. However, a high dose of ouabain can lead to ventricular...

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Strophanthin

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Strophanthus. The singular may refer to: g-Strophanthin, also known as ouabain k-Strophanthin Cardenolide This set index article lists chemical compounds...

Word Count : 58

Cardiac glycoside

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toxicaria (upas tree): antiarin Strophanthus kombe (Strophanthus vine): ouabain (g-strophanthin) and other strophanthins Digitalis lanata and Digitalis...

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Dystonia

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ouabain block of Na+ -K+ pumps in the cerebellum of a live mouse results in it displaying ataxia and dystonia. Ataxia is observed for lower ouabain concentrations...

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Strophanthus

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genus produce toxic alkaloids and cardiac glycosides g-strophanthin (syn. ouabain), k-strophanthin, and e-strophanthin. As ordinarily administered, the drug...

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Jens Christian Skou

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Post asked whether the enzyme was inhibited by ouabain. At this stage Skou was unaware that ouabain inhibited the pump, but he immediately telephoned...

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Ataxia

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ouabain block of Na+ -K+ pumps in the cerebellum of a live mouse results in it displaying ataxia and dystonia. Ataxia is observed for lower ouabain concentrations...

Word Count : 5946

Rostafuroxin

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Giuseppe (2006). "Rostafuroxin: An ouabain antagonist that corrects renal and vascular Na+-K+- ATPase alterations in ouabain and adducin-dependent hypertension"...

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Digitalis purpurea

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However, digitoxin, digoxin and several other cardiac glycosides, such as ouabain, are known to have steep dose-response curves, i.e., minute increases in...

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EPA list of extremely hazardous substances

Last Update:

Nitrogen dioxide N-Nitrosodimethylamine Norbormide Organorhodium complex Ouabain Oxamyl Oxetane, 3,3-bis(chloromethyl)- Oxydisulfoton Paraquat Paraquat...

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Somerton Man

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the purchase. (The drugs were later publicly identified as digitalis and ouabain, both cardenolide-type cardiac glycosides.) Hicks noted the only "fact"...

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Atovaquone

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PMID 11078770. Farag A, Wang P, et al. (May 2020). "Identification of Atovaquone, Ouabain and Mebendazole as FDA-Approved Drugs Targeting SARS-CoV-2". chemRxiv (preprint)...

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Calotropis gigantea

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Sodium Current Improves Cardiac Function during Sodium Pump Inhibition by Ouabain". Journal of Pharmacology and Experimental Therapeutics. 337 (2): 513–523...

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Albert Fraenkel

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pneumoniae as a cause of bacterial pneumonia and championed intravenous ouabain for use in heart failure. The Albert-Fraenkel-Plakette (Albert Fraenkel...

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Strophanthus gratus

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Tobago. Strophanthus gratus has been used in local traditional medicine: ouabain derived from the plant's seeds is used as a treatment for heart failure...

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Quinidine

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binding to the same receptor sites as the digitalis glycosides such as ouabain. The effect of quinidine on the ion channels is to prolong the cardiac...

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Senolytic

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Cintrat JC, Le Pavec G, Delaunay-Moisan A, et al. (September 2021). "Ouabain and chloroquine trigger senolysis of BRAF-V600E-induced senescent cells...

Word Count : 1986

Acokanthera

Last Update:

also occurs in Yemen. Its sap contains the deadly cardiotoxic glycoside ouabain. The sap is among the most commonly used in arrow poisons, including those...

Word Count : 199

Glucoside

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Strophanthin is the name given to two different compounds, g-strophanthin (ouabain) obtained from Strophanthus gratus and k-strophanthin from Stroph. kombé...

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Ozone

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2006-09-25. Retrieved 2006-10-11. Smith, LL (2004). "Oxygen, oxysterols, ouabain, and ozone: a cautionary tale". Free Radical Biology & Medicine. 37 (3):...

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List of poisonous plants

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Strophanthus gratus Apocynaceae The ripe seeds of this African plant contain ouabain, a potent cardiac glycoside that, when sufficiently concentrated, can induce...

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Oleandrin

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like ouabain and digoxin but has less effect than digoxin. It is however, just like its derivate oleandrigenin, a more potent glycoside than ouabain. Oleandrin...

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Arrow poison

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plants that contain cardiac glycosides, such as Acokanthera (possessing ouabain), oleander (Nerium oleander), milkweeds (Asclepias), or Strophanthus, all...

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Myotonia congenita

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been blocked in the underarm by infusion of the Na+/K+-ATPase-blocker Ouabain, no effect on warm-up was observed. Another hypothesis states that the...

Word Count : 3125

Cardenolide

Last Update:

digitoxin digitoxigenin digoxigenin digoxin medigoxin neoconvalloside ouabain strophanthidin Bufadienolide and marinobufagenin are similar in structure...

Word Count : 694

Membrane potential

Last Update:

off by removing their energy source, or by adding an inhibitor such as ouabain, the axon can still fire hundreds of thousands of action potentials before...

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Methylene blue

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incompletely understood; vital staining of nerve fibers in skin is prevented by ouabain, a drug that inhibits the Na/K-ATPase of cell membranes. Methylene blue...

Word Count : 5613

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