Bufalin

Bufalin Basic information
Pharmacological effects Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Product Name:Bufalin
Synonyms:22-dienolide,3,14-dihydroxy-,(3-beta,5-beta)-bufa-2;Bufalin, 98%, from bufonis venenum;Bufalin, >=98%;22-dienolide,3-beta,14-dihydroxy-5-beta-bufa-2;BUFA-20,22-DIENOLIDE, 3,14-DIHYDROXY-, (3B,5B)-;BUFALIN;(3BETA,5BETA)-3,14-DIHYDROXYBUFA-20,22-DIENOLIDE;3-BETA-14-DIHYDROXY-5-BETA-BUFA-20,22-DIENOLIDE
CAS:465-21-4
MF:C24H34O4
MW:386.52
EINECS:
Product Categories:Inhibitors;reference standards from Chinese medicinal herbs (TCM).;chemical reagent;pharmaceutical intermediate;phytochemical;standardized herbal extract;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
Mol File:465-21-4.mol
Bufalin Structure
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)


pka15.01±0.70(Predicted)
form White to off-white solid
InChIKeyQEEBRPGZBVVINN-ONGIWDLKSA-N
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 Information
Bufalin Usage And Synthesis
Pharmacological effectsBufalin 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.

CategoryToxic substances
Toxicity gradingHighly toxic
Acute toxicityIntraperitoneal-mouse LD50: 2.2 mg/kg
Flammability and hazard characteristicsFlammable,the fire produces acrid smoke .
Storage CharacteristicsVentilated, low-temperature ,dry storeroom,separate from food raw materials .
Extinguishing agentWater, carbon dioxide, dry powder,sandy soil
UsesA 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.
UsesBufalin 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

DefinitionChEBI: 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 DescriptionBufalin 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.
HazardToxic.
Biochem/physiol ActionsBufalin 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 inhibitorThis 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 Preparation Products And Raw materials
Plinol 7-OCTEN-2-OL, 2-METHYL-6-METHYLENE 1-ETHOXY-1-HEXENE VINYL ACRYLATE 1-ETHOXY-1-HEPTENE hex-1-enyl acetate ALLYLCYCLOPENTANE 1-BUTENYL ETHYL ETHER (-)-NEOMENTHOL CIS-2-NONEN-1-OL hept-1-enyl acetate 3-(Hydrogen suberoyl)bufalin,Bufalin-3-hydrogen suberate 2,6-DIMETHYLCYCLOHEXANOL 1-CYCLOHEXYL-2,2-DIMETHYL-1-PROPANOL ALPHA-PYRONE ALLYL VINYL ETHER 1-ETHOXY-1-PENTENE Bufalin

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