lucanthone
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443927477
| IUPAC_name = 1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
| image = Lucanthone.png
| width = 150
| image2 = Lucanthone molecule ball.png
| width2 = 220
| alt2 = Ball-and-stick model of the lucanthone molecule
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 479-50-5
| ATC_prefix = none
| ATC_suffix =
| PubChem = 10180
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04967
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 51052
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 9772
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FC6D57000M
| C=20 | H=24 | N=2 | O=1 | S=1
}}
Lucanthone is a drug used to treat parasitic diseases such as bilharziasis{{cite journal | vauthors = Blair DM | title = Lucanthone hydrochloride; a review | journal = Bulletin of the World Health Organization | volume = 18 | issue = 5–6 | pages = 989–1010 | date = 1958 | pmid = 13573122 | pmc = 2537946 | doi = | url = }} and schistosomiasis{{cite book | vauthors = Standen O | chapter = Chemotherapy of Helminthic Infections | veditors = Schnitzer RJ, Hawking F |title=Experimental chemotherapy. | volume = 1 |date=1963 |publisher=Academic Press |location=New York, New York |isbn=978-1-4832-7308-2 |page=770 | chapter-url = https://books.google.com/books?id=3C0SBQAAQBAJ&dq=Lucanthone&pg=PA770}} It is a prodrug and is converted to the active metabolite hycanthone.{{cite journal | vauthors = Rosi D, Peruzzotti G, Dennis EW, Berberian DA, Freele H, Tullar BF, Archer S | title = Hycanthone, a new active metabolite of lucanthone | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 5 | pages = 867–76 | date = September 1967 | pmid = 4963368 | doi = 10.1021/jm00317a025 }}
Mechanism of action
Hycanthone binds to acetylcholine receptors in the worm{{cite journal | vauthors = Hillman GR, Senft AW | title = Anticholinergic properties of the antischistosomal drug hycanthone | journal = The American Journal of Tropical Medicine and Hygiene | volume = 24 | issue = 5 | pages = 827–34 | date = September 1975 | pmid = 1190369 | doi = 10.4269/ajtmh.1975.24.827 }} 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
{{Reflist}}
{{Anthelmintics}}
{{Chemotherapeutic agents}}
{{antineoplastic-drug-stub}}