Bufalin

Bufalin
Names
	IUPAC name 3β,14-Dihydroxy-5β-bufa-20,22-dienolide
	Preferred 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 originally isolated from the Chinese toad venom. It is a component found in many Chinese traditional medicine.[1][2]

Usage

Bufalin has an in vitro antitumor effects against various malignancies, including hepatocellular[3] and lung carcinoma.[4] However, as with other bufadienolides, its use is hampered by its cardiotoxicity.[5]

References

"Datasheet: Bufotalin sc-sc-200136" Santa Cruz Biotechnology, Inc.https://datasheets.scbt.com/sc-200136.pdf
Okada, Masahiro; Suga, Toshiro; et al. (April 1960). "Pharmacology of the priniciples isolated from Senso (Ch'an Su) the dried venom of the Chinese toad (IV)" (PDF). Asian Medical Journal. 3 (4): 155–160.
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.
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.
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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[santacruz-1] "Datasheet: Bufotalin sc-sc-200136" Santa Cruz Biotechnology, Inc.https://datasheets.scbt.com/sc-200136.pdf

[Okada1960-2] Okada, Masahiro; Suga, Toshiro; et al. (April 1960). "Pharmacology of the priniciples isolated from Senso (Ch'an Su) the dried venom of the Chinese toad (IV)" (PDF). Asian Medical Journal. 3 (4): 155–160.

[pmid_=_24581171-3] 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.

[pmid_=_24871662-4] 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.

[pmid_=_21084181-5] 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.