Bufadienolide

Bufadienolide
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
CAS Number	29565-35-3 [EPA];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:83977 ;
ChemSpider	26286947 ;
PubChem CID	3035030;
CompTox Dashboard (EPA)	DTXSID70276154 ;
	InChI InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 Key: YBPMPRDOWHIVNA-JTSGVHQASA-N ; InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 Key: YBPMPRDOWHIVNA-JTSGVHQASA-N;
	SMILES CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5;
Properties
Chemical formula	C24H34O2
Molar mass	354.534 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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,^[2] and the saturated equivalent is bufanolide.^[3]

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:^[4]^[5]

Polycyclic compounds
- Steroids
  - Cardanolides
    - Cardiac glycosides
      - Bufanolides (includes bufenolides, bufadienolides, bufatrienolides)
        Proscillaridin
        
        Daigremontianin
      - Cardenolides

References

^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 534, 538. ISBN 3-8047-1763-2.
^ Glitsch, H. G.; Pusch, H.; Zylka, Ch. (1990). "The action of 22,23-dihydrobufalin and other cardioactive steroids on contraction and active sodium/potassium transport of sheep cardiac Purkinje fibres". Naunyn-Schmiedeberg's Archives of Pharmacology. 342 (5): 598–604. doi:10.1007/BF00169051. PMID 2090954. S2CID 21474014.
^ IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
^ Bufadienolides at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
^ Cardenolides at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

Etymology

Classification

References

Further reading