Bufalin Chemical Properties

Melting point:

242-243°

alpha 

D -20°

Boiling point:

556.6±50.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO:36.0(Max Conc. mg/mL);93.14(Max Conc. mM)
DMF:25.0(Max Conc. mg/mL);64.68(Max Conc. mM)
Ethanol:27.5(Max Conc. mg/mL);71.15(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:2):0.3(Max Conc. mg/mL);0.78(Max Conc. mM)

pka

15.01±0.70(Predicted)

form 

White to off-white solid

color 

White to off-white

InChIKey

QEEBRPGZBVVINN-ONGIWDLKSA-N

SMILES

O[C@]12CC[C@H](C3=COC(C=C3)=O)[C@]1(CC[C@]1([H])[C@]3(CC[C@@H](C[C@@]3([H])CC[C@@]21[H])O)C)C

Safety Information

Hazard Codes 

T+

Risk Statements 

28

Safety Statements 

28-36/37-45

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

EI2962500

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29322090

MSDS

• Language:English Provider:3-b,14-Dihydroxy-5-beta-bufa-20,22-dienolide
• Language:English Provider:SigmaAldrich

Bufalin Usage And Synthesis

Pharmacological effects

Bufalin is one of the main components of dried secretions of toad which is Bufo , Bufalin has a strong surface anesthetic effect, and it has a long-lasting effect in rabbit cornea and human tongue tests which is stronger than cocaine, about 90 times of cocaine. intravenous fluid Toad (0.05mg/kg) on Anesthetized rabbits , anesthetized rabbits can be caused breathing excitement, cat can also be caused breathe excitement . Its effect is stronger than nikethamide , pentylenetetrazol, lobeline, etc. and it can antagonize morphine respiratory depression. Respiratory stimulant order: Bufalin>Resibufogenin= Cinobufagin =cinobufotaline> Japanese toad toxins.
Bufalin low concentrations (10-4) promote release of presynaptic acetylcholine on rat diaphragm , while high concentrations promote first then inhibit, and partly antagonize the neuromuscular blocking effects of Mg2 +,but no inhibition on choline esterase.
The above information is edited by the Chemicalbook of Tian Ye.

Category

Toxic substances

Toxicity grading

Highly toxic

Acute toxicity

Intraperitoneal-mouse LD50: 2.2 mg/kg

Flammability and hazard characteristics

Flammable,the fire produces acrid smoke .

Storage Characteristics

Ventilated, low-temperature ,dry storeroom,separate from food raw materials .

Extinguishing agent

Water, carbon dioxide, dry powder,sandy soil

Chemical Properties

It comes from the dried secretions of toads such as the Chinese giant toad Bufo bufo gargarizans Cantor or the black-spotted toad Bufo melanostictus Schneider.

Uses

Bufalin has been used:

• to test its effect on invasion and activation of nuclear factor kappa- B (NF-κB) cells and tumor necrosis factor-α (TNF-α) stimulated rheumatoid arthritis fibroblast-like synoviocytes (RAFLSs)
• as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytes
• to test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib

Uses

A bufadienolide derivative, cardiac steroid, a component of bufadienolides present in the traditional Chinese medicine Chan'su, used therapeutically for the treatment of heart disease, also has been reported as a protective factor in many tumors.

Definition

ChEBI: A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.

General Description

Bufalin is a C-24 steroid with an α-pyrone ring positioned at C-17. It is present in the venom glands and skin of toad, Venenum Bufonis. Bufalin is a cardiotonic steroid and is digoxin-like component of Chan Su.

Hazard

Toxic.

Biochem/physiol Actions

Bufalin is an anti-metastasis drug, which elicits anti-tumor functionality by favoring cell cycle arrest and apoptosis in various cancer types including hepatocellular, bladder and osteosarcoma. It also promotes autophagic cell death and possesses anti-inflammatory properties. Bufalin is a steroid receptor coactivator (SRC) inhibitor.

Enzyme inhibitor

This cardioactive C-24 steroid (FW = 386.52 g/mol; CAS 465-21-4; Solubility: 5 mg/mL chloroform, 25 mg/mL DMSO), also named 3,14- dihydroxybufa-20,22-dienolide;5β,20(22)-bufadienolide-3β,14-diol and 3β,14-dihydroxy-5β,20(22)-bufadienolide, is the major digoxin-like immunoreactive component of Chansu, a traditional Chinese medicine prepared from the skin and venom-containing parotid gland of a poisonous toad. Bufalin increases the doubling time of three prostate cancer cell lines, inducing apoptosis and the caspase-3 activity. Expression of other proapoptoptic factors, such as mitochondrial Bax and cytosolic cytochrome c, were also increased. Bufalin also reduces serum-induced invasiveness of human hepatocellular cancer SK-Hep1 cells, markedly inhibiting MMP-2 and MMP-9 activities. It also attenuates phosphoinisitide-3-kinase (PI3K) and AKT phosphorylation was associated with reduced levels of NF- κB. Bufalin also suppresses protein levels of FAK, Rho A, VEGF, MEKK3, MKK7, and uPA. Such observations indicate that bufalin is as an antiinvasive agent that inhibits MMP-2 and -9 and alters PI3K/AKT and NF- κB signaling pathways.

Bufalin(465-21-4)Related Product Information

• Cinobufagin
• Costunolide
• CIS-2-NONEN-1-OL
• VINYL ACRYLATE
• 2,6-DIMETHYLCYCLOHEXANOL
• 1-BUTENYL ETHYL ETHER
• ALLYLCYCLOPENTANE
• 7-OCTEN-2-OL, 2-METHYL-6-METHYLENE
• Bufalin
• ALPHA-PYRONE
• ALLYL VINYL ETHER
• NEORUSCOGENIN
• (-)-NEOMENTHOL
• hex-1-enyl acetate
• 1-ETHOXY-1-PENTENE
• 1-ETHOXY-1-HEXENE
• 3α-Bufalin
• 1-ETHOXY-1-HEPTENE