Hycanthone

Hycanthone
Clinical data
ATC code
  • none
Identifiers
  • 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.512 Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2O2S
Molar mass356.48 g·mol−1
3D model (JSmol)
  • CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O
  • 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
 ☒NcheckY (what is this?)  (verify)

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.[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

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. ^ Teoh NC, Chitturi S, Farrell GC (2010). "Chapter 86: Liver Disease Caused by Drugs". In Feldman M, Friedman LS, Brandt LJ (eds.). Sleisenger and Fordtran's Gastrointestinal and Liver Disease. Vol. 2 (Ninth ed.). Saunders Elsevier. pp. 1413–1446. doi:10.1016/B978-1-4160-6189-2.00086-X. ISBN 978-1-4160-6189-2.
  4. ^ Stine JG, Lewis JH (2013). "Hepatotoxicity of Antibiotics: A Review and Update for the Clinician". Clinics in Liver Disease. 17 (4): 609–642. doi:10.1016/j.cld.2013.07.008. PMID 24099021.
  5. ^ 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.
  6. ^ "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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