Bufotalin

Source: Wikipedia, the free encyclopedia.
Bufotalin
Names
IUPAC name
3β,14-Dihydroxy-5β-bufa-20,22-dienolid-16β-yl acetate
Systematic IUPAC name
(1R,2S,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-Dihydroxy-9a,11a-dimethyl-1-(1-oxo-1H-oxan-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1 checkY
    Key: VOZHMAYHYHEWBW-NVOOAVKYSA-N checkY
  • InChI=1/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1
    Key: VOZHMAYHYHEWBW-NVOOAVKYBX
  • CC(=O)O[C@H]1C[C@@]2(C3CC[C@@H]4C[C@H](CC[C@@]4(C3CC[C@@]2([C@H]1C5=COC(=O)C=C5)C)C)O)O
Properties
C26H36O6
Molar mass 444.568 g·mol−1
Appearance crystalline solid
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Lethal dose or concentration (LD, LC):
4.13 mg·kg−1 (mouse,
IV
)

0.4 mg·kg−1 (mouse,

SC
)
0.136 mg·kg−1 (cat, IV)[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Bufotalin is a

cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species.[2][3] Bufotalin can be extracted from the skin parotoid glands
of several types of toad.

Sources

Bufo bufo (common European toad) are sources of bufotalin.[2][3][4]

Traditional medicine

Bufotalin is part of Ch'an Su, a traditional Chinese medicine used for cancer. It is also known as Venenum Bufonis or senso (Japanese).[5]

Toxicity

Specifically, in cats the lethal median dose is 0.13 mg/kg.[1] and in dogs is 0.36 mg/kg (intravenous).[6]

Knowing this it is advisable to monitor those functions continuously using an EKG. As there is no antidote against bufotalin all occurring symptoms need to be treated separately or if possible in combination with others. To increase the clearance theoretically, due to the similarities with digitoxin,

bile salt, might help.[6] Recent animal studies have shown that taurine restores cardiac functions.[7]

Symptomatic measures include

hyperkalaemia from its effect on the Na+/K+ ATPase pump.[6]

Pharmacology and mechanism of action

After a single intravenous injection, bufotalin gets quickly distributed and eliminated from the blood plasma with a half-time of 28.6 minutes and a MRT of 14.7 min. After 30 minutes after an administration of bufotalin, the concentrations within the brain and lungs are significantly higher than those in blood and other tissues.

BH3 interacting domain death agonist and STAT proteins.[9]

Bufotalin induces apoptosis

apoptosis inducing factor (AIF).[10]
The use of bufotalin as a cancer treating compound is still in the experimental phase. It also arrests cell cycle at G(2)/M, by up- and down- regulation of several enzymes.

Pharmacokinetics

The mechanism of the biotransformation of bufotalin is still unknown. Researches found, that bufotalin is biotransformed into at least 5 different compounds.[11]

The five known biotransformation products of bufotalin.

Chemical properties

If bufotalin is

esterified with suberyl arginine, the bufotalin-like steroid bufotoxin is obtained.[12]

References

  1. ^ a b "Datasheet: Bufotalin sc-202509" Santa Cruz Biotechnology, Inc.http://datasheets.scbt.com/sc-202509.pdf
  2. ^
    PMID 1325343. Archived from the original
    (PDF) on 2014-10-11. Retrieved 2014-03-05.
  3. ^
    PMID 9473822
    .
  4. PMID 23796725
    .
  5. PMID 22841670
    .
  6. ^ a b c Spoerke, DG (November 1986). "Toad Toxins".
  7. S2CID 7187045
    .
  8. S2CID 27185931
    .
  9. PMID 21887462
    .
  10. PMID 19055367
    .
  11. PMID 21636103
    .
  12. ISBN 978-0521363778
    .
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