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Merck
CN

C1147

Cinobufotalin

Synonym(s):

14,15β-Epoxy-3β,5α,16β-trihydroxy-5β,20(22)-bufadienolide 16-acetate, 5β,20(22)-Bufadienolide-14,15β-epoxy-3β,5α,16β-triol 16-acetate

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About This Item

Empirical Formula (Hill Notation):
C26H34O7
CAS Number:
1108-68-5
Molecular Weight:
458.54
NACRES:
NA.77
PubChem Substance ID:
24892362
UNSPSC Code:
12352200
MDL number:
MFCD28396383

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InChI

1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1

SMILES string

C[C@@]12[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]35O[C@@H]5[C@H](OC(C)=O)[C@@H]4C6=COC(C=C6)=O)(O)C[C@@H](O)CC1

InChI key

KBKUJJFDSHBPPA-ZNCGZLKOSA-N

form

solid

storage temp.

2-8°C

General description

Cinobufotalin is a cardiotonic steroid or bufotalin. It is mainly obtained from the skin secretion of the giant toad.

Application

Cinobufotalin has been used:
  • as a standard to bound them with the Fab fragment of an anti-digoxin antibody (Digibind) to rapidly detect its presence in blood by the fluorescence polarization immunoassay for digitoxin
  • to treat human cancer cell lines/MCF-7 cells to examine the steroid receptor coactivator-3 (SRC-3) protein concentrations and evaluate its efficacy as SRC small-molecule inhibitors (SMIs)
  • as a standard to calibrate the high-performance liquid chromatography (HPLC) and calculate the total quantity of bufadienolides present in the nuchal gland fluid of Rhabdophis tigrinus

Biochem/physiol Actions

Cinobufotalin, a diuretic, and a hemostatic agent can stimulate cytotoxic effect in cultured lung cancer cells. It can suppress the development of A549 cells in vivo. Cinobufotalin possesses antitumor activity and enhanced chemotherapeutic effect. It can inhibit the vascular endothelial growth factor and epidermal growth factor receptor expression to prevent the development and metastasis of the tumor. It may be beneficial to advance gastric cancer (GC) patients. This safe auxiliary antitumor agent can reduce the adverse events related to chemotherapy.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
070F0341

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Huiling Sun et al.
OncoTargets and therapy, 12, 3139-3160 (2019-05-24)
Purpose: This study aimed to investigate the efficacy and safety of combining cinobufotalin and chemotherapy for advanced gastric cancer (GC). Patients and methods: Literature retrieval was performed in Cochrane Library, Web of Science, PubMed, Embase, China National Knowledge Infrastructure (CNKI)
D A Hutchinson et al.
Journal of zoology (London, England : 1987), 289(4), 270-278 (2013-07-16)
Species that sequester toxins from prey for their own defense against predators may exhibit population-level variation in their chemical arsenal that reflects the availability of chemically defended prey in their habitat.
Ting-Ting Wang et al.
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine, 29(10), 915-917 (2010-01-16)
To investigate the effect of cinobufagin on the proliferation of lens epithelial cells (LECs) and the bcl-2 and bax mRNA expressions of rabbits. Cultured LECs were treated for 72 h with cinobufagin of different concentrations, the end titer was 0.1
Kun Feng et al.
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine, 30(11), 1183-1185 (2011-02-01)
To investigate the inhibitory effect of cinobufotalin (CBT) on the growth of xenograft endometrial carcinoma cell line ishikawa in nude mice, and its impact on the expression of ribonucleotide reductase subunit M2 (RRM2). Eleven nude mice with xenograft were randomly
J R Brubacher et al.
Chest, 110(5), 1282-1288 (1996-11-01)
Toxicity from toad venom poisoning is similar to digoxin toxicity and carries a high mortality rate. We report on six previously healthy men who developed vomiting and bradycardia after ingesting a purported topical aphrodisiac. Each patient had positive apparent digoxin
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