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Bufalin

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Bufalin
Names
IUPAC name 3β,14-Dihydroxy-5β-bufa-20,22-dienolide
Systematic IUPAC name 4-phenanthren-1-yl]-2H-pyran-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.150.073 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: QEEBRPGZBVVINN-BMPKRDENSA-N
SMILES
  • C12CC(C1CC32CC4(3(CC4c5ccc(=O)oc5)O)C)O
Properties
Chemical formula C24H34O4
Molar mass 386.532 g·mol
Hazards
GHS labelling:
Pictograms GHS06: Toxic
Signal word Danger
Hazard statements H300
Precautionary statements P264, P270, P301+P310, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bufalin is a cardiotonic steroid toxin originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines.

Research

Bufalin has in vitro antitumor effects against various malignant cell lines, including hepatocellular and lung carcinoma. However, as with other bufadienolides, its potential use is hampered by its cardiotoxicity.

References

  1. A Dasgupta, P Datta (1998). "Rapid detection of cardioactive bufalin toxicity using fluorescence polarization immunoassay for digitoxin". Ther Drug Monit. 20 (1): 104–108. doi:10.1097/00007691-199802000-00019. PMID 9485564.
  2. "Datasheet: Bufotalin sc-sc-200136" (PDF). Santa Cruz Biotechnology, Inc.
  3. Okada, Masahiro; Suga, Toshiro; et al. (April 1960). "Pharmacology of the principles isolated from Senso (Ch'an Su) the dried venom of the Chinese toad (IV)" (PDF). Asian Medical Journal. 3 (4): 155–160.
  4. Zhang ZJ (Feb 2014). "Bufalin attenuates the stage and metastatic potential of hepatocellular carcinoma in nude mice". J Transl Med. 12: 57. doi:10.1186/1479-5876-12-57. PMC 4015709. PMID 24581171.
  5. Wu SH (2014). "Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways". Am J Chin Med. 42 (3): 729–42. doi:10.1142/S0192415X14500475. PMID 24871662.
  6. Ma H (Jul 2012). "The novel antidote Bezoar Bovis prevents the cardiotoxicity of Toad (Bufo bufo gargarizans Canto) Venom in mice". Exp Toxicol Pathol. 64 (5): 417–23. doi:10.1016/j.etp.2010.10.007. PMID 21084181.
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