Bufalin
Bufalin Basic information
- 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:
- 386.53
- 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 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
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
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.
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
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.
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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