Hycanthone
Chemical compound
title: "Hycanthone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiparasitic-agents", "thioxanthones", "diethylamino-compounds"] description: "Chemical compound" topic_path: "general/antiparasitic-agents" source: "https://en.wikipedia.org/wiki/Hycanthone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 407389823 | IUPAC_name = 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone | image = Hycanthone.png | image_class = skin-invert-image
| 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 = | CAS_number = 3105-97-3 | ATC_prefix = none | ATC_suffix = | PubChem = 3634 | DrugBank_Ref = | DrugBank = | UNII_Ref = | UNII = 2BXX5EVN2A | ChEBI_Ref = | ChEBI = 52768 | KEGG_Ref = | KEGG = D00541 | ChEMBL_Ref = | ChEMBL = 22077 | ChemSpiderID_Ref = | ChemSpiderID =3508 | StdInChI_Ref = | StdInChI = 1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = MFZWMTSUNYWVBU-UHFFFAOYSA-N
| chemical_formula = | C=20 | H=24 | N=2 | O=2 | S=1 | smiles = CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O
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.
Anti-schistosomal activity
Hycanthone is shown to be an effective inhibitor of acetylcholinesterase (AChE) from Schistosoma mansoni, but is less potential against AChE from mammalian origin. This might come from differences in the configuration of active center between schistosome and mammalian AChE enzymes.
Hycanthone is shown to intercalate into DNA and inhibit RNA synthesis in vitro. A growing body of evidence has shown that hycathone has an antineoplastic activity.
Toxicity
Hycanthone is a dose-dependent hepatotoxin, causing hepatocellular injury.
Clinical trials
- Phase II Study of Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.
- Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)
Physical properties
::data[format=table]
| logP | 3.74 |
|---|---|
| :: |
References
References
- "hycanthone". NCI Cancer Dictionary.
- (September 1975). "Anticholinergic properties of the antischistosomal drug hycanthone". The American Journal of Tropical Medicine and Hygiene.
- (2010). "Sleisenger and Fordtran's Gastrointestinal and Liver Disease". Saunders Elsevier.
- (2013). "Hepatotoxicity of Antibiotics: A Review and Update for the Clinician". Clinics in Liver Disease.
- (June 1983). "Phase II study of hycanthone in patients with advanced colorectal carcinoma". Cancer Treatment Reports.
- "Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas". U.S. National Cancer Institute.
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