Cinobufagin

Names

[ CAS No. ]:
470-37-1

[ Name ]:
Cinobufagin

[Synonym ]:
Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3-hydroxy-, (3β,5β,15β,16β)-
(3β,5β,15β,16β)-16-Acetoxy-3-hydroxy-14,15-epoxybufa-20,22-dienolide
5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,16β-dihydroxy-, 16-acetate (8CI)
cinobufagine
Bufa-20,22-dienolide, 16- (acetyloxy)-14,15-epoxy-3-hydroxy-, (3β,5β,15β,16β)-
CINOBUFAGIN(P)
UNII:T9PSN4R8IR
5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,16β-dihydroxy-, 16-acetate
MFCD00056825
RARECHEM BK HC T302
Cinobufagin
(3β,5β,15β,16β)-16-(acetyloxy)-3-hydroxy-14,15-epoxybufa-20,22-dienolide

Biological Activity

[Description]:

Cinobufagin, a kind of Chinese materia medica with antitumor effect, is widely used in clinical practice, especially in anti-liver cancer.IC50 value:Target:In vitro: Cinobufagin inhibited proliferation of cancer cells at doses of 0.1, 1, or 10 μM after 2–4 days of culture. Cytotoxicity of cinobufagin on the DU145 and LNCaP cells was dose-dependent. Cinobufagin increased [Ca2+]i and apoptosis in cancer cells after a 24-hr culture as well as caspase 3 activities in DU145 and PC3 cells and caspase 9 activities in LNCaP cells [1]. Cinobufagin suppresses cell proliferation and causees apoptosis in prostate cancer cells via a sequence of apoptotic modulators, including Bax, cytochrome c and caspases [2].In vivo:

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Natural Products >> Steroids

Research Areas >> Cancer

[References]

[1]. Zhang G, et al. Cinobufagin inhibits tumor growth by inducing intrinsic apoptosis through AKT signaling pathway in human nonsmall cell lung cancer cells. Oncotarget. 2016 Mar 3.

[2]. Yu Y, et al. Immunomodulatory Effects of Cinobufagin on Murine Lymphocytes and Macrophages. Evid Based Complement Alternat Med. 2015;2015:835263.

[3]. Baek SH, et al. Cinobufagin exerts anti-proliferative and pro-apoptotic effects through the modulation ROS-mediated MAPKs signaling pathway. Immunopharmacol Immunotoxicol. 2015 Jun;37(3):265-73.

[4]. Jiun-Yih Yeh, et al. Effects of bufalin and cinobufagin on the proliferation of androgen dependent and independent prostate cancer cells. The ProstateVolume 54, Issue 2, pages 112–124, 1 February 2003

[5]. Yu CH, et al. Apoptotic signaling in bufalin- and cinobufagin-treated androgen-dependent and -independent human prostate cancer cells. Cancer Science, 2008, 99 (12): 2467-2476

[6]. Peng Bei, et al. Progress in study on basic and clinical application in treating liver cancer by Cinobufagin Injection. Drug Evaluation Research, 2011-01

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
595.4±50.0 °C at 760 mmHg

[ Melting Point ]:
222-223ºC

[ Molecular Formula ]:
C₂₆H₃₄O₆

[ Molecular Weight ]:
442.545

[ Flash Point ]:
199.4±23.6 °C

[ Exact Mass ]:
442.235535

[ PSA ]:
89.27000

[ LogP ]:
2.43

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.595

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EI2955000

CHEMICAL NAME :: Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3-hydroxy-, (3-beta,5-beta,15-beta,16-beta)-

CAS REGISTRY NUMBER :: 470-37-1

LAST UPDATED :: 199709

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C26-H34-O6

MOLECULAR WEIGHT :: 442.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 144 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Behavioral - ataxia

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 86,269,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1210 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 :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 230 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 49,561,1933

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 209 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 *** REVIEWS *** TOXICOLOGY REVIEW 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,189,1963

Safety Information

[ Symbol ]:

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 ]:
S22-S36/37/39-S45

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
GD7850000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
3001200090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 3001200090

Articles

Microbial transformation of cinobufagin by Syncephalastrum racemosum.

J. Nat. Prod. 71 , 1268-70, (2008)

Microbial transformation of a cytotoxic bufadienolide, cinobufagin (1), was performed by Syncephalastrum racemosum. The six metabolites obtained were identified as 7beta-hydroxycinobufagin ( 2), 12bet...

Preparative separation of four major bufadienolides from the Chinese traditional medicine, Chansu, using high-speed counter-current chromatography.

Nat. Prod. Commun. 5(7) , 1031-4, (2010)

A preparative, high-speed, counter-current chromatographic (HSCCC) method for the isolation and purification of bufadienolides from Chansu was successfully developed by using stepwise elution with a t...

Cinobufacini induced MDA-MB-231 cell apoptosis-associated cell cycle arrest and cytoskeleton function.

Bioorg. Med. Chem. Lett. 22(3) , 1459-63, (2012)

Cinobufacini is a traditional Chinese anti-tumor drug and widely used in clinic experiences. But little is known about its effect on the cells. In this study, the effects of cinobufacini on breast can...