Bufadienolide

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Bufadienolide
Bufadienolide skeletal.svg
Names
IUPAC name
5-[(5R, 8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
Identifiers
ChEBI CHEBI:83977 N
ChemSpider 26286947 YesY
Jmol-3D images Image
PubChem 3035030
Properties
C24H34O2
Molar mass 354.53 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest.[1]

Etymology[edit]

The term derives from the toad genus Bufo that contains bufadienolide glycosides, the suffix -adien- that refers to the two double bonds in the lactone ring, and the ending -olide that denotes the lactone structure. Consequently, related structures with only one double bond are called bufenolides,[citation needed] and the saturated equivalent is bufanolide.[2]

Bufanolide

Classification[edit]

According to MeSH, bufadienolides and bufanolides are classified as follows:[3][4]

Cardenolides have been classified under cardanolides as well as cardiac glycosides in this classification.

References[edit]

  1. ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 534, 538. ISBN 3-8047-1763-2. 
  2. ^ IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
  3. ^ Bufadienolides at the US National Library of Medicine Medical Subject Headings (MeSH)
  4. ^ Cardenolides at the US National Library of Medicine Medical Subject Headings (MeSH)