| Identification | Back Directory | [Name]
Bufalin | [CAS]
465-21-4 | [Synonyms]
BUFALIN
Bufalin std.
BUFALIN90%,99%
Bufalin, >=98%
5β,20(22)-Bufadienolide-3β,14-diol
3,14-dihydroxybufa-20,22-dienolide
3β,14-Dihydroxy-5β,20(22)-bufadienolide
5BETA,20[22]-BUFADIENOLIDE-3BETA,14-DIOL
(3β,5β)-3,14-Dihydroxy-bufa-20,22-dienolide
3-b,14-Dihydroxy-5-beta-bufa-20,22-dienolide
3BETA,14-DIHYDROXY-5BETA,20[22]-BUFADIENOLIDE
22-dienolide,3-beta,14-dihydroxy-5-beta-bufa-2
BUFA-20,22-DIENOLIDE, 3,14-DIHYDROXY-, (3B,5B)-
3-BETA-14-DIHYDROXY-5-BETA-BUFA-20,22-DIENOLIDE
(3BETA,5BETA)-3,14-DIHYDROXYBUFA-20,22-DIENOLIDE
22-dienolide,3,14-dihydroxy-,(3-beta,5-beta)-bufa-2
Bufa-20,22-dienolide, 3,14-dihydroxy-, (3-beta,5-beta)-
BUFALIN: BUFA-20,22-DIENOLIDE, 3,14-DIHYDROXY-, (3B,5B)-,
3β,14-Dihydroxy-5β,20(22)-bufadienolide, 5β,20(22)-Bufadienolide-3β,14-diol
Bufalin,3β,14-Dihydroxy-5β,20(22)-bufadienolide, 5β,20(22)-Bufadienolide-3β,14-diol
5-(3,14-Dihydroxy-13-methyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pyran-2-one
5-(3,14-Dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pyran-2-one | [Molecular Formula]
C24H34O4 | [MDL Number]
MFCD00056525 | [MOL File]
465-21-4.mol | [Molecular Weight]
386.52 |
| Chemical Properties | Back Directory | [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) | [form ]
White to off-white solid | [pka]
15.01±0.70(Predicted) | [color ]
White to off-white | [InChIKey]
QEEBRPGZBVVINN-ONGIWDLKSA-N |
| Hazard Information | Back Directory | [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. | [Hazard]
Toxic. | [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. | [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. |
| Safety Data | Back Directory | [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 |
| Questions And Answer | Back Directory | [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
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