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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

Key Documents

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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)
Xin Liu et al.
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine, 28(2), 105-107 (2008-04-05)
To investigate the effect of traditional Chinese medicine (TCM) on quality of life (QOF) and survival period in patients with progressive gastric cancer, and thus exploring its clinical efficacy. TCM therapy applied in the 34 patients assigned in the TCM
A Dasgupta et al.
Life sciences, 63(9), 781-788 (1998-09-18)
Oleandrin plant poisoning is common in children and the plant extract is used in Chinese medicines. The toxicity is due to oleandrin and the deglycosylated metabolite oleandrigenin. Bufalin and cinobufotalin (toad cardiac toxins) are also widely used in Chinese medicines
A A Brownlee et al.
Clinical science (London, England : 1979), 78(2), 169-174 (1990-02-01)
1. We have reported that the bufadienolide, bufalin (purified from toad skin), was more potent than ouabain in inhibiting the sodium/potassium-dependent adenosine triphosphatase from canine kidney (Sigma) [Brownlee, A.A., Lee, G. & Mills, I.H.J. Physiol. (London) 1987; 390, 94P]. 2.
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.
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