Hycanthone

Hycanthone
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.512
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Chemical and physical data
FormulaC20H24N2O2S
Molar mass356.48 g·mol−1
3D model (JSmol)
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
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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 intercalates into DNA and inhibit RNA synthesis in vitro. A growing body of evidence has shown that hycathone has an antineoplastic activity.

Clinical trials

  • Phase II Study of Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.[3]
  • Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)[4]

Physical properties

Physical stateSolid
SolubilitySoluble in ethanol, methanol, DMSO, and water
Absorption maximum233, 258, 329, 438 nm
Melting point173-176 °C
logP3.74

References

  1. ↑ "hycanthone". NCI Cancer Dictionary.
  2. ↑ Hillman GR, Senft AW (September 1975). "Anticholinergic properties of the antischistosomal drug hycanthone". The American Journal of Tropical Medicine and Hygiene. 24 (5): 827–34. doi:10.4269/ajtmh.1975.24.827. PMID 1190369.
  3. ↑ Schutt AJ, Dalton RJ, Kovach JS, Moertel CG, O'Connell MJ (June 1983). "Phase II study of hycanthone in patients with advanced colorectal carcinoma". Cancer Treatment Reports. 67 (6): 593–4. PMID 6861166.
  4. ↑ "Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas". U.S. National Cancer Institute. Archived from the original on 13 February 2015.
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