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CAS 471-95-4

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Bufotalin

Description:
Bufotalin is a naturally occurring cardiac glycoside primarily derived from the skin of certain toads, particularly the Bufo species. It is known for its potent pharmacological effects, particularly in the context of its ability to influence cardiac function. Bufotalin exhibits a structure characterized by a steroid nucleus with a lactone ring, which is typical of cardiac glycosides. This compound has been studied for its potential therapeutic applications, including its use in traditional medicine for treating heart conditions, although it also poses risks due to its toxicity. Bufotalin functions by inhibiting the Na+/K+ ATPase enzyme, leading to increased intracellular calcium levels, which enhances cardiac contractility. However, its narrow therapeutic window necessitates caution, as overdoses can result in severe side effects, including arrhythmias and gastrointestinal disturbances. Research continues to explore its mechanisms of action and potential benefits in various medical applications, while also addressing safety concerns associated with its use.
Formula:C26H36O6
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
InChI key:InChIKey=VOZHMAYHYHEWBW-NVOOAVKYSA-N
SMILES:C[C@@]12[C@H]([C@@H](OC(C)=O)C[C@]1(O)[C@]3([C@](CC2)([C@]4(C)[C@](CC3)(C[C@@H](O)CC4)[H])[H])[H])C=5C=CC(=O)OC5
Synonyms:
  • (3Beta,5Beta,8Xi,9Xi,16Beta)-16-(Acetyloxy)-3,14-Dihydroxybufa-20,22-Dienolide
  • (3β,5β,16β)-16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide
  • 16-(Acetyloxy)-3,14-Dihydroxybufa-20,22-Dienolide
  • 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate
  • 5β-Bufa-20,22-dienolide, 3β,14,16β-trihydroxy-, 16-acetate
  • Bufa-20,22-dienolide, 16-(acetyloxy)-3,14-dihydroxy-, (3β,5β,16β)-
  • Bufotalin
  • NSC 89596
Found 7 products.