Cinobufotalin

Modify Date: 2025-08-25 19:24:01

Cinobufotalin Structure
Cinobufotalin structure
 Common Name Cinobufotalin
CAS Number 1108-68-5 Molecular Weight 458.544
Density 1.3±0.1 g/cm3 Boiling Point 627.3±55.0 °C at 760 mmHg
Molecular Formula C26H34O7 Melting Point 259 - 262ºC
MSDS Chinese USA Flash Point 210.7±25.0 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Cinobufotalin


Cinobufotalin is one of the bufadienolides prepared from toad venom; has anticancer activity.IC50 value:Target:in vitro: Cinobufotalin(CB) caused significant DNA fragmentation, decrease of MMP, and an increase in the intracellular Ca(2+) ion and ROS production. In addition, CB induced upregulation of Fas protein, proteolytic activation of cytochrome c, caspase-2, -3, -8 and -9 together with the activation of Bid and Bax [1]. cinobufotalin displayed considerable cytotoxicity against lung cancer cells (A549, H460 and HTB-58 lines) without inducing significant cell apoptosis. cinobufotalin mainly induces Cyp-D-dependent non-apoptotic death in cultured lung cancer cells [2]. cinobufotalin (at nmol/L) significantly inhibited HCC cell growth and survival while inducing considerable cell apoptosis. Further, cinobufotalin inhibited sphingosine kinase 1 (SphK1) activity and induced pro-apoptotic ceramide production. cinobufotalin inactivated Akt-S6K1 signaling in HepG2 cells, which was again inhibited by ceramide synthase-1 shRNA-depletion [3].in vivo: Using a mice xenograft model, we found that cinobufotalin inhibited A549 lung cancer cell growth in vivo [2].

 Names

Name Cinobufotalin
Synonym More Synonyms

 Cinobufotalin Biological Activity

Description Cinobufotalin is one of the bufadienolides prepared from toad venom; has anticancer activity.IC50 value:Target:in vitro: Cinobufotalin(CB) caused significant DNA fragmentation, decrease of MMP, and an increase in the intracellular Ca(2+) ion and ROS production. In addition, CB induced upregulation of Fas protein, proteolytic activation of cytochrome c, caspase-2, -3, -8 and -9 together with the activation of Bid and Bax [1]. cinobufotalin displayed considerable cytotoxicity against lung cancer cells (A549, H460 and HTB-58 lines) without inducing significant cell apoptosis. cinobufotalin mainly induces Cyp-D-dependent non-apoptotic death in cultured lung cancer cells [2]. cinobufotalin (at nmol/L) significantly inhibited HCC cell growth and survival while inducing considerable cell apoptosis. Further, cinobufotalin inhibited sphingosine kinase 1 (SphK1) activity and induced pro-apoptotic ceramide production. cinobufotalin inactivated Akt-S6K1 signaling in HepG2 cells, which was again inhibited by ceramide synthase-1 shRNA-depletion [3].in vivo: Using a mice xenograft model, we found that cinobufotalin inhibited A549 lung cancer cell growth in vivo [2].
Related Catalog
References

[1]. Kai S, et al. Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent. Biochem Biophys Res Commun. 2014 Sep 26;452(3):768-74.

[2]. Cheng L, et al. Ceramide production mediates cinobufotalin-induced growth inhibition and apoptosis in cultured hepatocellular carcinoma cells. Tumour Biol. 2015 Feb 28.

[3]. Emam H, et al. Apoptotic cell death by the novel natural compound, cinobufotalin. Chem Biol Interact. 2012 Sep 30;199(3):154-60.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 627.3±55.0 °C at 760 mmHg
Melting Point 259 - 262ºC
Molecular Formula C26H34O7
Molecular Weight 458.544
Flash Point 210.7±25.0 °C
Exact Mass 458.230438
PSA 109.50000
LogP 0.79
Vapour Pressure 0.0±4.2 mmHg at 25°C
Index of Refraction 1.612
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EI2991000
CHEMICAL NAME :
5-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta,5,16-beta-trihydroxy-, 16-acetate
CAS REGISTRY NUMBER :
1108-68-5
LAST UPDATED :
199012
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C26-H34-O
MOLECULAR WEIGHT :
362.60
WISWESSER LINE NOTATION :
T E6 B6653 1A R AX RO QHTTTT&J EQ GQ J1 N1 POV1 O- ET6O BHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5150 ug/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - antipsychotic
REFERENCE :
CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,1714,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,189,1963
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
199 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PAHEAA Pharmaceutica Acta Helvetiae. (Schweizerische Apothekerzeitung, Postfach 3006, CH3000 Bern, 7, Switzerland) V.1- 1926- Volume(issue)/page/year: 24,222,1949

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300-H310-H330
Precautionary Statements P260-P264-P280-P284-P302 + P350-P310
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+: Very toxic;
Risk Phrases R26/27/28
Safety Phrases 22-36/37/39-45
RIDADR UN 2811
WGK Germany 3
RTECS EI2991000
Packaging Group II
Hazard Class 6.1(a)

 Precursor & DownStream

Precursor  2

DownStream  0

 Articles15

More Articles
Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent.

Biochem. Biophys. Res. Commun. 452(3) , 768-74, (2014)

Lung cancer is a major cause of cancer-related mortality in the United States and around the world. Due to the pre-existing or acquired chemo-resistance, the current standard chemotherapy regimens onl...

Ceramide production mediates cinobufotalin-induced growth inhibition and apoptosis in cultured hepatocellular carcinoma cells.

Tumour Biol. 36 , 5763-71, (2015)

Hepatocellular carcinoma (HCC) is a highly aggressive and lethal neoplasm with poor prognosis. The aim of this study is to investigate the anticancer activity of cinobufotalin, a bufadienolide isolate...

Comparative Analysis of the Bufonis Venenum by Using TLC, HPLC, and LC-MS for Different Extraction Methods.

J Pharmacopuncture 15 , 52-65, (2015)

Toad venom, called Chan-Su, is a traditional Oriental medicine secreted from the auricular and the skin glands of the Bufo bufo gargarizanz Cantor or B. melanosticus Schneider and has been widely used...

 Synonyms

14,15b-Epoxy-3b,5a,16b-trihydroxy-5b,20(22)-bufadienolide 16-acetate
(3b,5b,15b,16b)-16-(Acetyloxy)-14,15-epoxy-3,5-dihydroxybufa-20,22-dienolide
MFCD00055946
Bufa-20,22-dienolide, 16- (acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-
5beta-Hydroxycinobufagin
5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,5,16β-trihydroxy-, 16-acetate (8CI)
Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-
cinobufotalin venom toad
Cinobufotlin
14,15-Epoxy-14H-cyclopenta[a]phenanthrene,bufa-20,22-dienolide deriv.
Cinobufotalin
CINOBUFOTALIN(RG)
cinobufatolin
(3β,5β,15β,16β)-16-Acetoxy-3,5-dihydroxy-14,15-epoxybufa-20,22-dienolide
14,15b-Epoxy-3b,5,16b-trihydroxy-5b-bufa-20,22-dienolide 16-Acetate
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Chemsrc provides Cinobufotalin(CAS#:1108-68-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Cinobufotalin are included as well.>> amp version: Cinobufotalin

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