bufalin
{{Chembox
| ImageFile = Bufalin.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = 3β,14-Dihydroxy-5β-bufa-20,22-dienolide
| SystematicName = 4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2H-pyran-2-one
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 465-21-4
| PubChem = 9547215
| ChemSpiderID = 7826155
| ChEBI = 517248
| ChEMBL = 399680
| UNII = U549S98QLW
| SMILES = C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4c5ccc(=O)oc5)O)C)O
| StdInChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
| StdInChIKey = QEEBRPGZBVVINN-BMPKRDENSA-N
}}
| Section2 = {{Chembox Properties
| C=24|H=34|O=4
| Appearance =
| Density =
| MeltingPt =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSSignalWord = Danger
| GHSPictograms = {{GHS06}}
| HPhrases = {{H-phrases|300}}
| PPhrases = {{P-phrases|264|270|301+310|321|330|405|501}}
}}
}}
Bufalin is a cardiotonic steroid toxin{{cite journal | journal = Ther Drug Monit | date = 1998 | volume = 20 | issue = 1 | pages = 104–108 | doi = 10.1097/00007691-199802000-00019 | title = Rapid detection of cardioactive bufalin toxicity using fluorescence polarization immunoassay for digitoxin | author = A Dasgupta, P Datta | pmid = 9485564 }} originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines.{{cite web | title = Datasheet: Bufotalin sc-sc-200136 | publisher = Santa Cruz Biotechnology, Inc. | url = https://datasheets.scbt.com/sc-200136.pdf }}{{cite journal |last1=Okada |first1=Masahiro |last2=Suga |first2=Toshiro |display-authors=etal |date=April 1960 |title=Pharmacology of the principles isolated from Senso (Ch'an Su) the dried venom of the Chinese toad (IV) |url=http://www.med.or.jp/english/journal/amj/0304/0304.pdf |journal=Asian Medical Journal |volume=3 |issue=4 |pages= 155–160}}
Research
Bufalin has in vitro antitumor effects against various malignant cell lines, including hepatocellular{{cite journal | author = Zhang ZJ | title = Bufalin attenuates the stage and metastatic potential of hepatocellular carcinoma in nude mice. | journal = J Transl Med | volume = 12 |date=Feb 2014 | pmid = 24581171 | doi = 10.1186/1479-5876-12-57 | pmc=4015709 | pages=57 | doi-access = free }} and lung carcinoma.{{cite journal | author = Wu SH | title = Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways | journal = Am J Chin Med | volume = 42 | issue = 3|date= 2014 | pmid = 24871662 | doi = 10.1142/S0192415X14500475 | pages=729–42}} However, as with other bufadienolides, its potential use is hampered by its cardiotoxicity.{{cite journal | author = Ma H | title = The novel antidote Bezoar Bovis prevents the cardiotoxicity of Toad (Bufo bufo gargarizans Canto) Venom in mice | journal = Exp Toxicol Pathol. | volume = 64 | issue = 5|date=Jul 2012 | pmid = 21084181 | doi = 10.1016/j.etp.2010.10.007 | pages=417–23}}