Hycanthone

Hycanthone
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone;
CAS Number	3105-97-3 ;
PubChem CID	3634;
ChemSpider	3508 ;
UNII	2BXX5EVN2A;
KEGG	D00541 ;
ChEBI	CHEBI:52768 ;
ChEMBL	ChEMBL22077 ;
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 ; Key:MFZWMTSUNYWVBU-UHFFFAOYSA-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 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

^ "hycanthone". NCI Cancer Dictionary.
^ 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.
^ 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.
^ 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.
^ 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.
^ "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.

[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.

[pmid6861166-5] 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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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
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