Bufotalin

Bufotalin

Names
IUPAC name ((3S,5R,10S,13R,14S,16S,17R)-3,14-Dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl)acetate
Identifiers
CAS Number	471-95-4 Y
3D model (JSmol)	Interactive image
ChemSpider	16735710 Y
PubChem CID	10119
InChI 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 Y Key: VOZHMAYHYHEWBW-NVOOAVKYSA-N Y 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
SMILES 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
Chemical formula	C26H36O6
Molar mass	444.57 g·mol−1
Appearance	crystalline solid
Hazards
Main hazards	Toxic
Lethal dose or concentration (LD, LC):
LD50 (median dose)	4.13 mg·kg−1 (mouse, IV) 0.4 mg·kg−1 (mouse, SC) 0.136 mg·kg−1 (cat, IV)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

0.4 mg·kg⁻¹ (mouse, SC)
0.136 mg·kg⁻¹ (cat, IV)

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

Rhinella marina (Cane toad), Rhaebo guttatus (Smooth-sided toad), Bufo melanostictus (Asian toad), and Bufo bufo (common European toad) are sources of bufotalin.

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

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

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, cholestyramine, a bile salt, might help. Recent animal studies have shown that taurine restores cardiac functions.

Symptomatic measures include lignocaine, atropine and phenytoin for cardiac toxicity and intravenous potassium compounds to correct hyperkalaemia from its effect on the Na⁺/K⁺ ATPase pump.

Bufotalin is found to inhibit myocardial Na⁺/K⁺ ATPase activity by that increasing myocardial contractile force. Furthermore, bufotalin was not found to affect the heart-rate with those changes in myocardial Na⁺/K⁺ ATPase activity.