Bufalin

Bufalin

Names
IUPAC name 3β,14-Dihydroxy-5β-bufa-20,22-dienolide
Systematic IUPAC name 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
Identifiers
CAS Number	465-21-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:517248
ChEMBL	ChEMBL399680
ChemSpider	7826155
ECHA InfoCard	100.150.073
PubChem CID	9547215
UNII	U549S98QLW
CompTox Dashboard (EPA)	DTXSID90873563
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/s1 Key: QEEBRPGZBVVINN-BMPKRDENSA-N
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
Properties
Chemical formula	C24H34O4
Molar mass	386.532 g·mol−1
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

Bufalin is a cardiotonic steroid toxin ^[1] originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines. ^{[2] [3]}

Research

Bufalin has in vitro antitumor effects against various malignant cell lines, including hepatocellular ^[4] and lung carcinoma. ^[5] However, as with other bufadienolides, its potential use is hampered by its cardiotoxicity. ^[6]

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. Archived from the original (PDF) on 2017-04-27. Retrieved 2017-04-27.
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.