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Structure Database (LMSD)

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Common Name

Bufalin

Systematic Name

3β,14β-dihydroxy-5β-bufa-20,22-dienolide

Synonyms

LM ID

LMST01130001

Formula

C₂₄H₃₄O₄

Exact Mass

Calculate m/z

386.245711

Sum Composition

ST 24:4;O4

Status

Curated

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Classification

Biological Context

Bufalin is a cardiotonic steroid first isolated from toad venom and used in traditional Asian medicine.^1,2 It inhibits the Na+/K+-ATPase transporter (Kds = 42, 45, and 40 nM for the α1, α2, and α3 subunits, respectively).³ Intravenously administered bufalin is cleared rapidly, with a plasma half-life of 25 minutes in dogs and rats.⁴ Bufalin inhibits steroid receptor coactivator 1 (SRC-1) and SRC-3 at doses as low as 5 nM, promotes the degradation of SRC-3 protein, and inhibits cancer cell growth both in vitro and in vivo.⁵ It can also impact the action and expression of several other proteins and kinases as well as induce apoptosis in various cancer cells.^6,7

This information has been provided by Cayman Chemical

References

1. Yoshida, S., and Sakai, T. Effects of bufalin and related cardiotonic steroids in the neuromuscular junction. Jpn. J. Pharmacol. 23(6), 859-869 (1973).

2. Yin, P.H., Liu, X., Qiu, Y.Y., et al. Anti-tumor activity and apoptosis-regulation mechanisms of bufalin in various cancers: New hope for cancer patients. Asian Pac. J. Cancer Prev. 13(11), 5339-5343 (2012).

3. Wu, S.H., Hsiao, Y.T., Kuo, C.L., et al. Bufalin inhibits NCI-H460 human lung cancer cell metastasis in vitro by inhibiting MAPKs, MMPs, and NF-KB pathways. Am. J. Chin. Med. 43(6), 1247-1264 (2015).

4. Pavlovic, D. The role of cardiotonic steroids in the pathogenesis of cardiomyopathy in chronic kidney disease. Nephron Clin. Pract. 128(1-2), 11-21 (2014).

5. Hamlyn, J.M. Natriuretic hormones, endogenous ouabain, and related sodium transport inhibitors. Front. Endocrinol. (Lausanne) 5, (2015).

6. Katz, A., Lifshitz, Y., Bab-Dinitz, E., et al. Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. J. Biol. Chem. 285(25), 19582-19592 (2010).

7. Wang, Y., Lonard, D.M., Yu, Y., et al. Bufalin is a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1. Cancer Res. 74(5), 1506-1517 (2014).

String Representations

InChiKey (Click to copy)

QEEBRPGZBVVINN-BMPKRDENSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5=COC(=O)C=C5)CC[C@]4(O)[C@]3([H])CC[C@]2([H])C[C@@H](O)C1