Bufotaline

Modify Date: 2025-08-20 18:45:45

Bufotaline structure	Common Name	Bufotaline
	CAS Number	471-95-4	Molecular Weight	444.560
	Density	1.3±0.1 g/cm3	Boiling Point	591.7±50.0 °C at 760 mmHg
	Molecular Formula	C₂₆H₃₆O₆	Melting Point	223°C (rough estimate)
	MSDS	N/A	Flash Point	195.8±23.6 °C

Use of Bufotaline

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species; a novel anti-osteoblastoma agent.IC50 value:Target:in vitro: bufotalin induced osteoblastoma cell death and apoptosis in dose- and time-dependent manners. Further, bufotalin induced endoplasmic reticulum (ER) stress activation in osteoblastoma cells, the latter was detected by the induction of C/EBP homologous protein (CHOP), phosphorylation of inositol-requiring enzyme 1 (IRE1) and PKR-like endoplasmic reticulum kinase (PERK), as well as caspase-12 activation [1]. Bufotalin was the most potent active compound among these four bufadienolides, and it exerted stronger inhibitory effect on the viability of doxorubicin-induced multidrug resistant liver cancer cells (R-HepG2) than that of their parent cells HepG2. bufotalin treatment induced cell cycle arrest at G(2)/M phase through down-regulation of Aurora A, CDC25, CDK1, cyclin A and cyclin B1, as well as up-regulation of p53 and p21. Bufotalin treatment also induced apoptosis which was accompanied by decrease in mitochondrial membrane potential, increases in intracellular calcium level and reactive oxygen species production, activations of caspase-9 and -3, cleavage of poly ADP-ribose polymerase (PARP) as well as changes in the expressions of bcl-2 and bax [2]. Bufotalin promoted death receptor-mediated cell death, especially TRAIL-induced apoptosis, through activation of caspase-3 and PARP-1. Cotreatment of bufotalin with TRAIL resulted in the downregulation of anti-apoptotic proteins, including Bcl-XL, Mcl-1, survivin and XIAP, and the up-regulation of MAPKs and TRAIL receptor DR5. In addition, phosphorylation of STAT1 was strongly inhibited by bufotalin [3]. externalization of phosphatidylserine, accumulation of sub-G(1) cells, fragmentation of DNA, and formation of apoptotic bodies were observed in bufotalin-treated Hep 3B cells [4].

Name	Bufotaline
Synonym	More Synonyms

Description	Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species; a novel anti-osteoblastoma agent.IC50 value:Target:in vitro: bufotalin induced osteoblastoma cell death and apoptosis in dose- and time-dependent manners. Further, bufotalin induced endoplasmic reticulum (ER) stress activation in osteoblastoma cells, the latter was detected by the induction of C/EBP homologous protein (CHOP), phosphorylation of inositol-requiring enzyme 1 (IRE1) and PKR-like endoplasmic reticulum kinase (PERK), as well as caspase-12 activation [1]. Bufotalin was the most potent active compound among these four bufadienolides, and it exerted stronger inhibitory effect on the viability of doxorubicin-induced multidrug resistant liver cancer cells (R-HepG2) than that of their parent cells HepG2. bufotalin treatment induced cell cycle arrest at G(2)/M phase through down-regulation of Aurora A, CDC25, CDK1, cyclin A and cyclin B1, as well as up-regulation of p53 and p21. Bufotalin treatment also induced apoptosis which was accompanied by decrease in mitochondrial membrane potential, increases in intracellular calcium level and reactive oxygen species production, activations of caspase-9 and -3, cleavage of poly ADP-ribose polymerase (PARP) as well as changes in the expressions of bcl-2 and bax [2]. Bufotalin promoted death receptor-mediated cell death, especially TRAIL-induced apoptosis, through activation of caspase-3 and PARP-1. Cotreatment of bufotalin with TRAIL resulted in the downregulation of anti-apoptotic proteins, including Bcl-XL, Mcl-1, survivin and XIAP, and the up-regulation of MAPKs and TRAIL receptor DR5. In addition, phosphorylation of STAT1 was strongly inhibited by bufotalin [3]. externalization of phosphatidylserine, accumulation of sub-G(1) cells, fragmentation of DNA, and formation of apoptotic bodies were observed in bufotalin-treated Hep 3B cells [4].
Related Catalog	Signaling Pathways >> Others >> Others Natural Products >> Steroids Research Areas >> Cancer
References	[1]. Zhu YR, et al. Bufotalin-induced apoptosis in osteoblastoma cells is associated with endoplasmic reticulum stress activation. Biochem Biophys Res Commun. 2014 Aug 15;451(1):112-8. [2]. Zhang DM, et al. Bufotalin from Venenum Bufonis inhibits growth of multidrug resistant HepG2 cells through G2/M cell cycle arrest and apoptosis. Eur J Pharmacol. 2012 Oct 5;692(1-3):19-28. [3]. Waiwut P, et al. Bufotalin sensitizes death receptor-induced apoptosis via Bid- and STAT1-dependent pathways. Int J Oncol. 2012 Jan;40(1):203-8. [4]. Su CL, et al. Involvement of caspases and apoptosis-inducing factor in bufotalin-induced apoptosis of Hep 3B cells. J Agric Food Chem. 2009 Jan 14;57(1):55-61.

Description

Related Catalog

Signaling Pathways >> Others >> Others

Natural Products >> Steroids

Research Areas >> Cancer

References

[1]. Zhu YR, et al. Bufotalin-induced apoptosis in osteoblastoma cells is associated with endoplasmic reticulum stress activation. Biochem Biophys Res Commun. 2014 Aug 15;451(1):112-8.

[2]. Zhang DM, et al. Bufotalin from Venenum Bufonis inhibits growth of multidrug resistant HepG2 cells through G2/M cell cycle arrest and apoptosis. Eur J Pharmacol. 2012 Oct 5;692(1-3):19-28.

[3]. Waiwut P, et al. Bufotalin sensitizes death receptor-induced apoptosis via Bid- and STAT1-dependent pathways. Int J Oncol. 2012 Jan;40(1):203-8.

[4]. Su CL, et al. Involvement of caspases and apoptosis-inducing factor in bufotalin-induced apoptosis of Hep 3B cells. J Agric Food Chem. 2009 Jan 14;57(1):55-61.

Density	1.3±0.1 g/cm3
Boiling Point	591.7±50.0 °C at 760 mmHg
Melting Point	223°C (rough estimate)
Molecular Formula	C₂₆H₃₆O₆
Molecular Weight	444.560
Flash Point	195.8±23.6 °C
Exact Mass	444.251190
PSA	96.97000
LogP	2.54
Vapour Pressure	0.0±3.8 mmHg at 25°C
Index of Refraction	1.587
InChIKey	VOZHMAYHYHEWBW-NVOOAVKYSA-N
SMILES	CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1c1ccc(=O)oc1

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EI3150000

CHEMICAL NAME :: 5-beta-Bufa-20,22-dienolide, 3-beta,14,16-beta-trihydroxy-, 16-acetate

CAS REGISTRY NUMBER :: 471-95-4

LAST UPDATED :: 199109

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C26-H36-O6

MOLECULAR WEIGHT :: 444.62

WISWESSER LINE NOTATION :: L E5 B666TJ A1 E1 GOV1 IQ OQ F- ET6OVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 ug/kg

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

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 4,331,1971

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4130 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 :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1131 ug/kg

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

REFERENCE :: PHUZBI Pharmazie in Unserer Zeit. (VCH Pub., Inc., 303 N.W. 12th Ave., Deerfield Beach, FL 33441) V.1- 1972- Volume(issue)/page/year: 13,129,1984

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 980 ug/kg

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

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 152,571,1958

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 360 ug/kg

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

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 152,571,1958

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 136 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: 74,223,1942

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 130 ug/kg

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

REFERENCE :: PHUZBI Pharmazie in Unserer Zeit. (VCH Pub., Inc., 303 N.W. 12th Ave., Deerfield Beach, FL 33441) V.1- 1972- Volume(issue)/page/year: 13,129,1984

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 1200 ug/kg

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

REFERENCE :: AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. (Leipzig, Ger. Dem. Rep.) V.1-109, 1873-1925. For publisher information, see NSAPCC. Volume(issue)/page/year: 86,138,1920

RIDADR	UN 3172
Packaging Group	II
Hazard Class	6.1(a)
HS Code	29329990

Bufotaline

Bufotalin std.

16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide

BUFOTALIN(SH)

BUFOTALIN SULFATE

Bufa-20,22-dienolide, 16-(acetyloxy)-3,14-dihydroxy-, (3β,5β,16β)-

(3b,5b,16b)-16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide

(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate

5β-Bufa-20,22-dienolide, 3β,14,16β-trihydroxy-, 16-acetate (8CI)

Bufotalin

3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-Acetate

(3β,5β,16β)-16-Acetoxy-3,14-dihydroxybufa-20,22-dienolide

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Shanghai Nianxing Industrial Co., Ltd
China
Product Name: Bufotaline
Price: Check
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China
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DC Chemicals Limited
China
Product Name: Bufotaline
Price: $280.0/20mg
Purity: 98.0%
Delivery: 3 Day
Contact: Tony Cao
Email: sales@dcchemicals.com

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Bufotaline

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Bufotaline Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Synonyms

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.