Lucanthone

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Lucanthone
Lucanthone.png
Lucanthone molecule ball.png
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
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ECHA InfoCard 100.006.849 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H24N2OS
Molar mass 340.49 g·mol−1
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Lucanthone is a drug used to treat parasitic diseases such as bilharziasis [1] and schistosomiasis [2] It is a prodrug and is converted to the active metabolite hycanthone. [3]

Mechanism of action

Hycanthone binds to acetylcholine receptors in the worm [4] 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.

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Hycanthone is the schistosomicide approved by the FDA in 1975. It is a metabolite of lucanthone. Hycanthone interferes with parasite nerve function, resulting in paralysis and death. This agent also intercalates into DNA and inhibits RNA synthesis in vitro and shows potential antineoplastic activity.

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References

  1. Blair DM (1958). "Lucanthone hydrochloride; a review". Bulletin of the World Health Organization. 18 (5–6): 989–1010. PMC   2537946 . PMID   13573122.
  2. Standen O (1963). "Chemotherapy of Helminthic Infections". In Schnitzer RJ, Hawking F (eds.). Experimental chemotherapy. Vol. 1. New York, New York: Academic Press. p. 770. ISBN   978-1-4832-7308-2.
  3. Rosi D, Peruzzotti G, Dennis EW, Berberian DA, Freele H, Tullar BF, Archer S (September 1967). "Hycanthone, a new active metabolite of lucanthone". Journal of Medicinal Chemistry. 10 (5): 867–76. doi:10.1021/jm00317a025. PMID   4963368.
  4. Hillman GR, Senft AW (September 1975). "Anticholinergic properties of the antischistosomal drug hycanthone". The American Journal of Tropical Medicine and Hygiene. 24 (5): 827–34. doi:10.4269/ajtmh.1975.24.827. PMID   1190369.