667:
384:
361:
854:
all the required functionalities and stereochemistry needed to produce ouabain. The structure of E was confirmed by comparison against the degradation product of ouabain. Methylation of E, catalyzed by rhodium, produced F. The dehydroxylation and selective oxidation of the secondary hydroxy group of F produced G. G reacted with triphenyl phosphoranylidene ketene and the ester bonds in G were hydrolyzed to produce ouabagenin, a precursor to ouabain. The
680:
812:) has a broad, white-bordered strip of hairs covering an area of glandular skin on the flank. When the animal is threatened or excited, the mane on its back erects and this flank strip parts, exposing the glandular area. The hairs in this flank area are highly specialised; at the tips they are like ordinary hairs, but are otherwise spongy, fibrous, and absorbent. The rat is known to deliberately chew the roots and bark of the Poison-arrow tree (
711:(NCX), which pumps one calcium ion out of the cell and three sodium ions into the cell down their concentration gradient. Therefore, the decrease in the concentration gradient of sodium into the cell which occurs when the Na/K-ATPase is inhibited reduces the ability of the NCX to function. This in turn elevates intracellular calcium. This results in higher cardiac contractility and an increase in cardiac
797:
447:
29:
754:. A number of analytical techniques led to the conclusion that this circulating molecule was ouabain and that humans were producing it as an endogenous hormone. A large portion of the scientific community agreed that this inhibitor was endogenous ouabain and that there was strong evidence to indicate that it was synthesized in the
767:
endogenous ouabain detected other compounds or failed to detect ouabain at all. Additionally, it was suggested that rhamnose, the L-sugar component of ouabain, could not be synthesized within the body despite published data to the contrary. Yet another argument against the existence of endogenous ouabain was the lack of effect of
818:), which contains ouabain. After the rat has chewed the tree, instead of swallowing the poison it slathers the resulting masticate onto its specialised flank hairs which are adapted to absorb the poisonous mixture. It thereby creates a defense mechanism that can sicken or even kill predators which attempt to bite it.
853:
substitute B in a double
Michael addition to produce tricycle C. At the indicated position, C was reduced to the aldehyde and the alcohol group was protected with p-methoxybenzyl ether (PMB) to form the aldol precursor needed to produce D. After several steps, intermediate E was produced. E contained
766:
Despite widespread analytical confirmation, some questioned whether or not this endogenous substance is ouabain. The arguments were based less upon rigorous analytical data but more on the fact that immunoassays are neither entirely specific nor reliable. Hence, it was suggested that some assays for
894:
The poison was extracted from the branches and leaves of the plant by boiling them over a fire. Arrows would then be dipped into the concentrated black tar-like juice that formed. Often, certain magical additives were also mixed in with the ouabain extract in order to make the poison work according
732:
Ouabain is a highly toxic compound, however, it has a low bioavailability and is absorbed poorly from the alimentary tract as so much of the oral dose is destroyed. Intravenous administration results in greater available concentrations. After intravenous administration, the onset of action occurs
723:
An overdose of ouabain can be detected by the presence of the following symptoms: rapid twitching of the neck and chest musculature, respiratory distress, increased and irregular heartbeat, rise in blood pressure, convulsions, wheezing, clicking, and gasping rattling. Death is caused by cardiac
899:
and
Langulu poison makers would add an elephant shrew to the poison mixture in order to facilitate the pursuit of their prey. They had observed that an elephant shrew would always run straight ahead or follow a direct path and thought that these properties would be transferred to the poison. A
762:
of plant ouabain. However, this possibility was excluded by various methods including the synthesis of the 11 epimer and the demonstration that it has different chromatographic behavior from ouabain. Critically, the primary observations concerning the identification of ouabain in mammals were
907:
Although ouabain was used as an arrow poison primarily for hunting, it was also used during battle. One example of this occurred during a battle against the
Portuguese, who had stormed Mombasa in 1505. Portuguese records indicated that they had suffered a great deal from the poisoned arrows.
749:
In 1991, a specific high affinity sodium pump inhibitor indistinguishable from ouabain was first discovered in the human circulation and proposed as one of the potential mediators of long term blood pressure and the enhanced salt excretion following salt and volume loading. This agent was an
838:
924:
species. They were familiar with the deadly properties of these plants and brought samples back to Europe. Around this time, interest in the plant grew. It was known that ouabain was a cardiac poison, but there was some speculation about its potential medical uses.
489:
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
779:
Ouabain is no longer approved for use in the USA. In France and
Germany, however, intravenous ouabain has a long history in the treatment of heart failure, and some continue to advocate its use intravenously and orally in
900:
poisonous arrow made with this shrew was thought to cause the hunted animal to behave like the shrew and run in a straight path. In Rwanda members of the Nyambo tribe, also known poison arrow makers, harvest the
706:
sodium–potassium ion pump. Once ouabain binds to this enzyme, the enzyme ceases to function, leading to an increase of intracellular sodium. This increase in intracellular sodium reduces the activity of the
1494:"Main results of the ouabain and adducin for Specific Intervention on Sodium in Hypertension Trial (OASIS-HT): a randomized placebo-controlled phase-2 dose-finding study of rostafuroxin"
69:
788:
despite its poor and variable absorption. The positive properties of ouabain regarding the prophylaxis and treatment of these two indications are documented by several studies.
883:
reported a toxic substance that the
Ethiopians would smear on their arrows. The poisons derived from this genus of plants were used throughout eastern Africa, typically as
636:
826:
The total synthesis of ouabain was achieved in 2008 by
Deslongchamps laboratory in Canada. It was synthesized under the hypothesis that a polyanionic cyclization (double
51:
1959:
461:
1059:
891:, in particular, exhibits a very large amount of ouabain, which the Kenyans, Tanzanians, Rwandans, Ethiopians, and Somalis would use as an arrow poison.
834:) would allow access to a tetracyclic intermediate with the desired functionality. The figure below shows the key steps in the synthesis of ouabain.
1297:
Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP (April 2003). "11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications".
666:
628:
via amino acid substitutions, have been observed in certain species, namely some herbivore- insect species, that have resulted in toxin resistance.
1660:
763:
repeated and confirmed using a variety of tissue sources on three different continents with advanced analytical methods as summarized elsewhere.
1052:
758:. One early speculative interpretation of the analytical data led to the proposal that endogenous ouabain may have been the 11 epimer, i.e., an
632:
1142:
Yu SP, Choi DW (June 1997). "Na–Ca exchange currents in cortical neurons: concomitant forward and reverse operation and effect of glutamate".
2185:
1760:
639:(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
904:
plants according to how many dead insects are found under it - more dead insects under a shrub indicating a higher potency of poison.
715:. The change in ionic gradients caused by ouabain can also affect the membrane voltage of the cell and result in cardiac arrhythmias.
1596:
1118:
481:
1952:
1591:
Cowan T, MD, (2016) Human Heart, Cosmic Heart: A Doctor's Quest to
Understand, Treat and Prevent Cardiovascular Disease, Chap 9,
102:
920:
towards the end of the nineteenth century. British troops were the target of arrows poisoned with the extracts of various
1254:
Manunta P, Ferrandi M, Bianchi G, Hamlyn JM (January 2009). "Endogenous ouabain in cardiovascular function and disease".
771:(a first generation ouabain receptor antagonist) on blood pressure in an unselected population of hypertensive patients.
232:
2202:
1945:
1791:"Bioprospecting and Resistance: Transforming Poisoned Arrows into Strophantin Pills in Colonial Gold Coast, 1885-1922"
1053:"40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities"
340:
1829:"Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase"
1003:"Community-wide convergent evolution in insect adaptation to toxic cardenolides by substitutions in the Na,K-ATPase"
2264:
2254:
700:
622:
618:
2249:
1873:
1916:
Tanz RD (May 1964). "The Action of
Ouabain on Cardiac Muscle Treated with Reserpine and Dichloroisoproterenol".
2259:
617:
and in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the
708:
181:
2244:
2190:
917:
379:
2239:
1689:
Zhang H, Sridhar Reddy M, Phoenix S, Deslongchamps P (2008). "Total synthesis of ouabagenin and ouabain".
1492:
Staessen JA, Thijs L, Stolarz-Skrzypek K, Bacchieri A, Barton J, Espositi ED, et al. (January 2011).
301:
2269:
2229:
814:
785:
649:
172:
1609:
1441:
Malawista I, Davidson EA (December 1961). "Isolation and identification of rhamnose from rabbit skin".
929:
1664:
1450:
1306:
1198:
1063:
850:
655:
356:
127:
2234:
1574:
1474:
1330:
1279:
1167:
916:
European imperial expansion and exploration into Africa overlapped with the rise of the
European
831:
621:, also known as the sodium–potassium ion pump. However, adaptations to the alpha-subunit of the
322:
281:
1968:
1925:
1904:
1860:
1766:
1756:
1706:
1592:
1566:
1525:
1466:
1423:
1379:
1322:
1271:
1226:
1159:
1124:
1114:
1034:
614:
312:
41:
2144:
1894:
1850:
1840:
1802:
1733:
1698:
1556:
1515:
1505:
1458:
1413:
1369:
1361:
1314:
1263:
1216:
1206:
1185:
Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, et al. (July 1991).
1151:
1024:
1014:
945:
827:
553:
521:
396:
221:
241:
2085:
2054:
2013:
1635:
1631:
781:
599:
592:
136:
1454:
1310:
1202:
837:
679:
383:
360:
2196:
2031:
1899:
1882:
1855:
1828:
1520:
1493:
1374:
1349:
1318:
1155:
1110:
African ethnobotany : poisons and drugs : chemistry, pharmacology, toxicology
1029:
1002:
896:
1418:
1401:
1365:
2223:
2090:
1981:
1751:
Hoffman RS, Howland MA, Lewin NA, Nelson L, Goldfrank LR, Flomenbaum N (2014-12-23).
1561:
1544:
1221:
1186:
855:
755:
372:
61:
1334:
1283:
1171:
879:
plants are known to have been used in Africa as far back as the 3rd century BC when
2130:
2115:
2105:
2036:
1998:
1972:
1724:
Zhang H, Reddy MS, Phoenix S, Deslongchamps P (June 2008). "Synthesis of
Ouabain".
1578:
1478:
983:
884:
880:
768:
610:
161:
82:
77:
1187:"Identification and characterization of a ouabain-like compound from human plasma"
1267:
964:
110:
1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside)
2120:
2110:
2068:
2008:
1400:
Lewis LK, Yandle TG, Hilton PJ, Jensen BP, Begg EJ, Nicholls MG (October 2014).
796:
1833:
Proceedings of the National Academy of Sciences of the United States of America
1191:
Proceedings of the National Academy of Sciences of the United States of America
1007:
Proceedings of the National Academy of Sciences of the United States of America
2167:
733:
within 2–10 minutes in humans with the maximum effect enduring for 1.5 hours.
712:
423:
212:
1770:
2095:
2077:
2046:
2003:
1937:
1845:
1510:
1211:
1128:
1019:
933:
805:
751:
55:
1929:
1908:
1864:
1737:
1710:
1702:
1570:
1529:
1470:
1427:
1383:
1326:
1275:
1038:
936:. Ouabain was seen as a possible treatment for certain cardiac conditions.
699:
Ouabain is a cardiac glycoside that acts by non-selectively inhibiting the
1230:
1163:
2159:
1807:
1790:
928:
In 1882, ouabain was first isolated from the plant by the French chemist
859:
192:
201:
20:
2149:
2100:
609:, is a plant derived toxic substance that was traditionally used as an
147:
2023:
1462:
759:
292:
1108:
647:
Ouabain can be found in the roots, stems, leaves, and seeds of the
261:
28:
836:
795:
678:
665:
446:
437:
328:
272:
849:
from the Deslongchamps laboratory condensed cyclohexenone A with
1990:
252:
1941:
469:
O=C\1OC/C(=C/1)2CC6(O)2(C)C(O)46CC5(O)C(O3O((O)(O)3O)C)C(O)45CO
736:
Ouabain is eliminated by renal excretion, largely unchanged.
613:
in eastern Africa for both hunting and warfare. Ouabain is a
562:
536:
527:
345:
1883:"The Use of Circulatory Stimulants in the Care of the Sick"
635:
in the United States as defined in Section 302 of the U.S.
568:
1918:
The Journal of Pharmacology and Experimental Therapeutics
1827:
Dobler S, Dalla S, Wagschal V, Agrawal AA (August 2012).
1636:"African crested rat uses poison trick to foil predators"
1001:
Dobler S, Dalla S, Wagschal V, Agrawal AA (August 2012).
800:
The African crested rat smears toxins on its flank hairs.
583:
539:
1350:"Endogenous Ouabain: Recent Advances and Controversies"
506:
750:
inhibitor of the sodium pump that acted similarly to
580:
571:
559:
542:
524:
932:
as an amorphous substance, which he identified as a
659:
plants, both of which are native to eastern Africa.
565:
533:
2158:
2129:
2076:
2067:
2045:
2022:
1989:
1980:
1755:(Tenth ed.). New York: McGraw-Hill Education.
577:
556:
530:
435:
422:
395:
390:
371:
339:
311:
291:
271:
251:
231:
211:
191:
180:
171:
146:
126:
93:
68:
50:
40:
35:
637:Emergency Planning and Community Right-to-Know Act
160:
1610:"Giant rat kills predators with poisonous hair"
135:
1953:
8:
1663:. University of Oxford. 2011. Archived from
19:
1102:
1100:
1098:
1096:
1094:
1092:
1090:
1088:
1086:
1084:
2073:
1986:
1960:
1946:
1938:
1661:"Rat makes its own poison from toxic tree"
1549:International Journal of Clinical Practice
1348:Hamlyn JM, Blaustein MP (September 2016).
1299:Annals of the New York Academy of Sciences
382:
359:
220:
27:
1898:
1854:
1844:
1806:
1560:
1519:
1509:
1417:
1373:
1249:
1247:
1245:
1220:
1210:
1028:
1018:
978:
976:
974:
972:
965:"ouabain" in the World English Dictionary
240:
1784:
1782:
1780:
1684:
1682:
1395:
1393:
1691:Angewandte Chemie International Edition
957:
486:
466:
355:
200:
107:
895:to the hunter's wishes. In Kenya, the
373:
18:
841:Key steps in the synthesis of ouabain
321:
300:
280:
60:
7:
1887:Canadian Medical Association Journal
1545:"Ouabain - the insulin of the heart"
1144:The European Journal of Neuroscience
990:. U.S. National Library of Medicine.
327:
81:
1753:Goldfrank's toxicologic emergencies
1402:"Endogenous ouabain is not ouabain"
260:
151:
1319:10.1111/j.1749-6632.2003.tb07283.x
1156:10.1111/j.1460-9568.1997.tb01482.x
14:
1419:10.1161/hypertensionaha.114.03919
1366:10.1161/HYPERTENSIONAHA.116.06599
1562:10.1111/j.1742-1241.2010.02395.x
1543:Fürstenwerth H (November 2010).
552:
520:
407:
494:Key:LPMXVESGRSUGHW-HBYQJFLCSA-N
1789:Osseo-Asare AD (August 2008).
413:
401:
1:
633:extremely hazardous substance
114:4-phenanthren-17-yl]furan-2(5
1268:10.1097/hjh.0b013e32831cf2c6
2286:
1881:Rudolf RD (October 1922).
1795:Social History of Medicine
1060:Government Printing Office
845:In their synthesis, Zhang
391:Chemical and physical data
2180:
1876:. University of Maryland.
1058:(July 1, 2008 ed.).
887:for hunting and warfare.
598:, "arrow poison" through
502:
477:
457:
98:
26:
1237:Proc Natl Acad Sci U S A
709:sodium–calcium exchanger
62:International Drug Names
1846:10.1073/pnas.1202111109
1511:10.1186/1745-6215-12-13
1256:Journal of Hypertension
1239:1991 Nov 1; 88(21):9907
1212:10.1073/pnas.88.14.6259
1020:10.1073/pnas.1202111109
918:pharmaceutical industry
631:It is classified as an
1738:10.1055/s-2008-1072606
1703:10.1002/anie.200704959
1113:. Chapman & Hall.
842:
801:
687:
674:
1107:Neuwinger HD (1996).
889:Acokanthera schimperi
875:Poisons derived from
840:
815:Acokanthera schimperi
799:
792:Animal use of ouabain
786:myocardial infarction
682:
671:Acokanthera schimperi
669:
650:Acokanthera schimperi
1069:on February 25, 2012
1839:(32): 13040–13045.
1667:on November 6, 2013
1455:1961Natur.192..871M
1311:2003NYASA.986..685H
1203:1991PNAS...88.6259H
1013:(32): 13040–13045.
984:"Ouabain C29H44O12"
858:of ouabagenin with
806:African crested rat
695:Mechanism of action
684:Strophanthus gratus
656:Strophanthus gratus
23:
2207:Never to phase III
1969:Cardiac glycosides
1808:10.1093/shm/hkn066
930:Léon-Albert Arnaud
862:produced ouabain.
843:
832:aldol condensation
802:
745:Endogenous ouabain
740:Biological effects
688:
675:
16:Chemical substance
2265:ATPase inhibitors
2255:Tertiary alcohols
2217:
2216:
2176:
2175:
2063:
2062:
1762:978-0-07-180184-3
1555:(12): 1591–1594.
1197:(14): 6259–6263.
810:Lophiomys imhausi
692:
691:
615:cardiac glycoside
514:
513:
448:Interactive image
341:CompTox Dashboard
2277:
2250:Primary alcohols
2141:(g-Strophanthin)
2074:
1987:
1962:
1955:
1948:
1939:
1933:
1912:
1902:
1877:
1868:
1858:
1848:
1813:
1812:
1810:
1786:
1775:
1774:
1748:
1742:
1741:
1721:
1715:
1714:
1697:(7): 1272–1275.
1686:
1677:
1676:
1674:
1672:
1657:
1651:
1650:
1648:
1646:
1628:
1622:
1621:
1619:
1617:
1608:Welsh J (2011).
1605:
1599:
1589:
1583:
1582:
1564:
1540:
1534:
1533:
1523:
1513:
1489:
1483:
1482:
1463:10.1038/192871a0
1438:
1432:
1431:
1421:
1397:
1388:
1387:
1377:
1345:
1339:
1338:
1294:
1288:
1287:
1251:
1240:
1234:
1224:
1214:
1182:
1176:
1175:
1150:(6): 1273–1281.
1139:
1133:
1132:
1104:
1079:
1078:
1076:
1074:
1068:
1062:. Archived from
1057:
1049:
1043:
1042:
1032:
1022:
998:
992:
991:
980:
967:
962:
946:K-Strophanthidin
828:Michael addition
703:
662:
661:
625:
605:) also known as
590:
589:
586:
585:
582:
579:
574:
573:
570:
567:
564:
561:
558:
549:
548:
545:
544:
541:
538:
535:
532:
529:
526:
510:
509:
450:
430:
415:
409:
403:
386:
375:
364:
363:
349:
347:
331:
325:
304:
284:
264:
244:
224:
204:
184:
164:
154:
153:
139:
85:
64:
31:
24:
22:
2285:
2284:
2280:
2279:
2278:
2276:
2275:
2274:
2260:Total synthesis
2220:
2219:
2218:
2213:
2212:
2197:Clinical trials
2172:
2154:
2125:
2086:Acetyldigitoxin
2059:
2055:Daigremontianin
2041:
2018:
1976:
1966:
1936:
1915:
1893:(10): 697–701.
1880:
1871:
1826:
1822:
1817:
1816:
1788:
1787:
1778:
1763:
1750:
1749:
1745:
1723:
1722:
1718:
1688:
1687:
1680:
1670:
1668:
1659:
1658:
1654:
1644:
1642:
1630:
1629:
1625:
1615:
1613:
1607:
1606:
1602:
1590:
1586:
1542:
1541:
1537:
1491:
1490:
1486:
1449:(4805): 871–2.
1440:
1439:
1435:
1399:
1398:
1391:
1347:
1346:
1342:
1296:
1295:
1291:
1253:
1252:
1243:
1184:
1183:
1179:
1141:
1140:
1136:
1121:
1106:
1105:
1082:
1072:
1070:
1066:
1055:
1051:
1050:
1046:
1000:
999:
995:
982:
981:
970:
963:
959:
954:
942:
914:
873:
868:
824:
794:
782:angina pectoris
777:
747:
742:
730:
721:
701:
697:
645:
623:
576:
555:
551:
523:
519:
505:
503:
498:
495:
490:
485:
484:
473:
470:
465:
464:
453:
428:
418:
412:
406:
367:
343:
335:
307:
287:
267:
247:
227:
207:
187:
167:
150:
142:
122:
119:
113:
111:
106:
105:
89:
17:
12:
11:
5:
2283:
2281:
2273:
2272:
2267:
2262:
2257:
2252:
2247:
2245:Cyclopentanols
2242:
2237:
2232:
2222:
2221:
2215:
2214:
2211:
2210:
2209:
2208:
2205:
2194:
2188:
2182:
2181:
2178:
2177:
2174:
2173:
2171:
2170:
2164:
2162:
2156:
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2147:
2145:k-Strophanthin
2142:
2135:
2133:
2127:
2126:
2124:
2123:
2118:
2113:
2108:
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2098:
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2034:
2032:Proscillaridin
2028:
2026:
2020:
2019:
2017:
2016:
2011:
2006:
2001:
1995:
1993:
1984:
1982:Bufadienolides
1978:
1977:
1967:
1965:
1964:
1957:
1950:
1942:
1935:
1934:
1924:(2): 205–213.
1913:
1878:
1874:"Ouabainomics"
1869:
1823:
1821:
1820:External links
1818:
1815:
1814:
1801:(2): 269–290.
1776:
1761:
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1652:
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1584:
1535:
1484:
1433:
1412:(4): 680–683.
1389:
1360:(3): 526–532.
1340:
1305:(1): 685–693.
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607:g-strophanthin
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2240:Cyclohexanols
2238:
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2201:
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2198:
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2117:
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2109:
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2091:Acetyldigoxin
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2030:
2029:
2027:
2025:
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2015:
2014:Marinobufagin
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1996:
1994:
1992:
1988:
1985:
1983:
1979:
1974:
1970:
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1120:3-8261-0077-8
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903:
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886:
885:arrow poisons
882:
878:
870:
865:
863:
861:
857:
856:glycosylation
852:
848:
839:
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833:
829:
821:
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811:
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764:
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757:
756:adrenal gland
753:
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442:
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427:
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398:
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389:
385:
381:
378:
376:
374:ECHA InfoCard
370:
362:
358:
357:DTXSID0043765
354:
353:
351:
342:
338:
330:
329:RCSB PDB
324:
319:
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59:
57:
53:
49:
45:
43:
39:
36:Clinical data
34:
30:
25:
2270:Plant toxins
2230:Cardenolides
2138:
2131:Strophanthus
2116:Metildigoxin
2106:Lanatoside C
2069:Cardenolides
2037:Scilliroside
1999:Arenobufagin
1921:
1917:
1890:
1886:
1836:
1832:
1798:
1794:
1752:
1746:
1729:
1725:
1719:
1694:
1690:
1669:. Retrieved
1665:the original
1655:
1643:. Retrieved
1639:
1626:
1614:. Retrieved
1603:
1587:
1552:
1548:
1538:
1501:
1497:
1487:
1446:
1442:
1436:
1409:
1406:Hypertension
1405:
1357:
1354:Hypertension
1353:
1343:
1302:
1298:
1292:
1259:
1255:
1236:
1235:Erratum in:
1194:
1190:
1180:
1147:
1143:
1137:
1109:
1071:. Retrieved
1064:the original
1047:
1010:
1006:
996:
987:
960:
927:
922:Strophanthus
921:
915:
906:
901:
893:
888:
881:Theophrastus
876:
874:
846:
844:
830:followed by
825:
813:
809:
803:
778:
775:Medical uses
769:rostafuroxin
765:
748:
735:
731:
722:
698:
683:
670:
654:
648:
646:
630:
611:arrow poison
606:
602:
595:
516:
515:
504:
302:ChEMBL222863
282:CHEBI:472805
115:
2193:from market
2121:Gitoformate
2111:Deslanoside
2009:Cinobufagin
1872:Hamlyn JM.
1732:(6): 0562.
1671:November 2,
1645:November 2,
1262:(1): 9–18.
1073:October 29,
902:Aconkathera
877:Acokanthera
619:Na/K-ATPase
431: g·mol
380:100.010.128
94:Identifiers
42:Trade names
2224:Categories
2168:Peruvoside
952:References
728:Toxicology
713:vagal tone
436:3D model (
424:Molar mass
313:PDB ligand
242:5ACL011P69
213:ChemSpider
173:IUPHAR/BPS
128:CAS Number
103:IUPAC name
2235:Pyranoses
2203:Phase III
2191:Withdrawn
2096:Digitoxin
2078:Digitalis
2047:Kalanchoe
2004:Bufotalin
1771:861895453
1640:BBC.co.uk
1632:Morelle R
1616:August 2,
934:glycoside
822:Synthesis
752:digitalis
56:Drugs.com
46:Strodival
2160:Thevetia
1930:14183432
1909:20314209
1865:22826239
1726:Synfacts
1711:18183567
1634:(2011).
1571:20946265
1530:21235787
1471:14468825
1428:25001271
1384:27456525
1335:23738926
1327:12763919
1284:41618824
1276:19050443
1172:23146698
1129:34675903
1039:22826239
940:See also
860:rhamnose
724:arrest.
719:Symptoms
596:waabaayo
507:(verify)
193:DrugBank
137:630-60-4
70:ATC code
2150:Cymarin
2139:Ouabain
2101:Digoxin
1900:1706809
1856:3420205
1579:6749622
1521:3031200
1479:4285678
1451:Bibcode
1375:4982830
1307:Bibcode
1231:1648735
1199:Bibcode
1164:9215711
1030:3420205
988:PubChem
897:Giriama
866:History
851:Nazarov
704:-ATPase
643:Sources
626:-ATPase
603:ouabaïo
517:Ouabain
429:584.659
397:Formula
202:DB01092
148:PubChem
86:)
80: (
78:C01AC01
21:Ouabain
2186:WHO-EM
2024:Scilla
1928:
1907:
1897:
1863:
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1709:
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1498:Trials
1477:
1469:
1443:Nature
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1274:
1229:
1219:
1170:
1162:
1127:
1117:
1037:
1027:
912:Europe
871:Africa
847:et al.
760:isomer
600:French
593:Somali
591:(from
462:SMILES
293:ChEMBL
262:C01443
222:388599
162:439501
1575:S2CID
1475:S2CID
1331:S2CID
1280:S2CID
1222:52062
1168:S2CID
1067:(PDF)
1056:(PDF)
686:plant
673:plant
482:InChI
438:JSmol
320:OBN (
273:ChEBI
118:)-one
1991:Bufo
1973:C01A
1926:PMID
1905:PMID
1861:PMID
1767:OCLC
1757:ISBN
1707:PMID
1673:2013
1647:2013
1618:2011
1593:ISBN
1567:PMID
1526:PMID
1467:PMID
1424:PMID
1380:PMID
1323:PMID
1272:PMID
1227:PMID
1160:PMID
1125:OCLC
1115:ISBN
1075:2011
1035:PMID
804:The
784:and
702:Na/K
653:and
624:Na/K
323:PDBe
253:KEGG
233:UNII
182:4826
52:AHFS
1922:144
1895:PMC
1851:PMC
1841:doi
1837:109
1803:doi
1734:doi
1699:doi
1557:doi
1516:PMC
1506:doi
1459:doi
1447:192
1414:doi
1370:PMC
1362:doi
1315:doi
1303:986
1264:doi
1217:PMC
1207:doi
1152:doi
1025:PMC
1015:doi
1011:109
550:or
346:EPA
152:CID
83:WHO
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