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}}

Category:Antineoplastic drugs

Category:Thioxanthones

{{antineoplastic-drug-stub}}