Hycanthone Explained

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.^[1]

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.^[2]

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,^[3] causing hepatocellular injury.^[4]

Clinical trials

• Phase II Study of Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.^[5]
• Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)^[6]

Physical properties

Physical state	Solid
Solubility	Soluble in ethanol, methanol, DMSO, and water
Absorption maximum	233, 258, 329, 438 nm
Melting point	173-176 °C
logP	3.74

Notes and References

1. Web site: hycanthone . NCI Cancer Dictionary .
2. Hillman GR, Senft AW . Anticholinergic properties of the antischistosomal drug hycanthone . The American Journal of Tropical Medicine and Hygiene . 24 . 5 . 827–34 . September 1975 . 1190369 . 10.4269/ajtmh.1975.24.827 .
3. Book: Teoh NC, Chitturi S, Farrell GC. Chapter 86: Liver Disease Caused by Drugs. Sleisenger and Fordtran's Gastrointestinal and Liver Disease. Ninth. 1413-1446. 2. 2010. Feldman M, Friedman LS, Brandt LJ. Saunders Elsevier. 978-1-4160-6189-2. 10.1016/B978-1-4160-6189-2.00086-X.
4. Stine JG, Lewis JH. Hepatotoxicity of Antibiotics: A Review and Update for the Clinician. Clinics in Liver Disease. 17. 4. 2013. 609-642. 10.1016/j.cld.2013.07.008. 24099021.
5. Schutt AJ, Dalton RJ, Kovach JS, Moertel CG, O'Connell MJ . Phase II study of hycanthone in patients with advanced colorectal carcinoma . Cancer Treatment Reports . 67 . 6 . 593–4 . June 1983 . 6861166 .
6. Web site: Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas . https://web.archive.org/web/20150213213104/http://www.cancer.gov/clinicaltrials/search/view?cdrid=77360&version=HealthProfessional&protocolsearchid=10235377 . 13 February 2015 . U.S. National Cancer Institute .