Ouabain

Ouabain
Clinical data
Trade names	Strodival
AHFS/Drugs.com	International 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 ;
PubChem CID	439501;
IUPHAR/BPS	4826;
DrugBank	DB01092 ;
ChemSpider	388599 ;
UNII	5ACL011P69;
KEGG	C01443 ;
ChEBI	CHEBI:472805 ;
ChEMBL	ChEMBL222863 ;
PDB ligand	OBN (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0043765 ;
ECHA InfoCard	100.010.128
Chemical and physical data
Formula	C29H44O12
Molar mass	584.659 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 ; Key:LPMXVESGRSUGHW-HBYQJFLCSA-N ;
	(verify)

Ouabain /wɑːˈbɑːɪn/^[1] or /ˈwɑːbeɪn, 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]

^ "ouabain" in the World English Dictionary
^ Cite error: The named reference Pubchem was invoked but never defined (see the help page).
^ 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.
^ "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.

[1] "ouabain" in the World English Dictionary

[Pubchem-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.

[gov-right-know-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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