Hycanthone

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]

Hycanthone

Clinical data
ATC code	none
Identifiers
IUPAC name 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone
CAS Number	3105-97-3 Y
PubChem CID	3634
ChemSpider	3508 N
UNII	2BXX5EVN2A
KEGG	D00541 Y
ChEBI	CHEBI:52768 N
ChEMBL	ChEMBL22077 N
CompTox Dashboard (EPA)	DTXSID9023128
ECHA InfoCard	100.019.512
Chemical and physical data
Formula	C20H24N2O2S
Molar mass	356.48 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O
InChI InChI=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 N Key:MFZWMTSUNYWVBU-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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.^{[citation needed]}

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