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1108-68-5

1108-68-5 structure
1108-68-5 structure
  • Name: Cinobufotalin
  • Chemical Name: Cinobufotalin
  • CAS Number: 1108-68-5
  • Molecular Formula: C26H34O7
  • Molecular Weight: 458.544
  • Catalog: API Antineoplastic agents Natural source antineoplastic agents
  • Create Date: 2018-09-02 20:11:25
  • Modify Date: 2025-08-25 19:24:01
  • 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].
Name Cinobufotalin
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
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.
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

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
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  2

DownStream  0

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