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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O4
Molecular Weight 386.5244
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFALIN

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C5=COC(=O)C=C5)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=QEEBRPGZBVVINN-BMPKRDENSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H34O4
Molecular Weight 386.5244
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Bufalin is a traditional oriental medicines, originally isolated from the Chinese toad venom. Bufalin is a cardiotonic steroid that has the potential to induce differentiation and apoptosis of tumor cells. Research on bufalin has so far mainly involved leukemia, prostate cancer, gastric cancer and liver cancer, and has been confined to in vitro studies. The bufadienolides bufalin and cinobufagin have been shown to induce apoptosis in a wide spectrum of cancer cell. Bufalin has being shown to be a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1. Bufalin is a component of Huachansu, a Chinese medicine that comes from dried toad venom from the skin glands of Bufo bufo gargarizans Cantor or B.melanotictus Schneider, has been used in the treatment of various cancers in China.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
24.83 µM [IC50]
28.7 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
The typical dose of Huachansu used in China is 20-25 mL (approximatelty 15 mL/m2).
Route of Administration: Intravenous
In Vitro Use Guide
Under sub-lethal concentrations (from 25 up to 100 nM), bufalin significantly inhibits the invasion and migration nature of NCI-H460 cells that were measured by Matrigel Cell Migration Assay and Invasion System.
Substance Class Chemical
Record UNII
U549S98QLW
Record Status Validated (UNII)
Record Version