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 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 ;
(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 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 (Completed)
Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)[3]

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

NCI Cancer Dictionary
Hillman, GR; Senft, AW (1975). "Anticholinergic properties of the antischistosomal drug hycanthone". The American Journal of Tropical Medicine and Hygiene. 24 (5): 827–834. PMID 1190369.
http://www.cancer.gov/clinicaltrials/search/results?protocolsearchid=10235377

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] NCI Cancer Dictionary

[2] Hillman, GR; Senft, AW (1975). "Anticholinergic properties of the antischistosomal drug hycanthone". The American Journal of Tropical Medicine and Hygiene. 24 (5): 827–834. PMID 1190369.

[3] ttp://www.cancer.gov/clinicaltrials/search/results?protocolsearchid=10235377