Lucanthone

Chemical compound From Wikipedia, the free encyclopedia

Lucanthone (Miracil D, Myracyl D) is a drug used to treat parasitic diseases such as schistosomiasis,[1][2][3] which was invented in 1938 by Hans Mauss and colleagues at Bayer AG.[4][5] It is a prodrug and is converted to the active metabolite hycanthone.[6][7] It is no longer commonly used in humans due to hepatotoxicity,[8] especially after the subsequent development of safer drugs with similar efficacy such as praziquantel.

ATC code
  • none
Quick facts Clinical data, ATC code ...
Lucanthone
Ball-and-stick model of the lucanthone molecule
Clinical data
ATC code
  • none
Identifiers
  • 1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.006.849 Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2OS
Molar mass340.49 g·mol−1
 ☒NcheckY (what is this?)  (verify)
Close

Mechanism of action

Hycanthone binds to acetylcholine receptors in the worm[9] and results in increased sensitivity to stimulation by 5-HT causing increase in motility, paired worms are separated and reproduction is stopped. It causes damage of the integument and vitelline duct.

Research

Lucanthone also shows anti-cancer activity, and while it has never been approved for medical use as a chemotherapy drug due to its toxicity, it has been tested in human clinical trials as an adjuvant therapy to increase the effectiveness of other chemotherapy medications, and continues to be used in cancer research.[10][11][12][13][14][15][16][17][18][19][20]

Synthesis

The original synthesis route by Mauss and colleagues produces a mixture of isomers which then needs to be separated,[21] this was subsequently improved upon in the 1950s.[22]

Lucanthone synthesis
Lucanthone improved precursor

References

Related Articles

Wikiwand AI