Lucanthone

Lucanthone
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one;
CAS Number	479-50-5 ;
PubChem CID	10180;
DrugBank	DB04967 ;
ChemSpider	9772 ;
UNII	FC6D57000M;
ChEBI	CHEBI:51052 ;
CompTox Dashboard (EPA)	DTXSID6023230 ;
ECHA InfoCard	100.006.849
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.

References

^ Blair DM (1958). "Lucanthone hydrochloride; a review". Bulletin of the World Health Organization. 18 (5–6): 989–1010. PMC 2537946. PMID 13573122.
^ 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.
^ 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.
^ 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.