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  Y
PubChem CID	10180
DrugBank	DB04967  Y
ChemSpider	9772  N
UNII	FC6D57000M
ChEBI	CHEBI:51052  N
CompTox Dashboard (EPA)	DTXSID6023230
ECHA InfoCard	100.006.849
Chemical and physical data
Formula	C20H24N2OS
Molar mass	340.49 g·mol−1
NY  (what is this?)    (verify)

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

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.