hycanthone

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 407389823

| IUPAC_name = 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone

| image = Hycanthone.png

| tradename =

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| routes_of_administration =

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 3105-97-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3634

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 2BXX5EVN2A

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 52768

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00541

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 22077

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID =3508

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MFZWMTSUNYWVBU-UHFFFAOYSA-N

| chemical_formula =

| C=20 | H=24 | N=2 | O=2 | S=1

| smiles = CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O

}}

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.{{cite web | title = hycanthone | url = http://www.cancer.gov/drugdictionary?cdrid=39477 | work = NCI Cancer Dictionary }}

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.{{cite journal | vauthors = Hillman GR, Senft AW | title = Anticholinergic properties of the antischistosomal drug hycanthone | journal = The American Journal of Tropical Medicine and Hygiene | volume = 24 | issue = 5 | pages = 827–34 | date = September 1975 | pmid = 1190369 | doi = 10.4269/ajtmh.1975.24.827 }}

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.{{cn|date=December 2022}}

Toxicity

Hycanthone is a dose-dependent hepatotoxin,{{cite book|vauthors=Teoh NC, Chitturi S, Farrell GC|chapter=Chapter 86: Liver Disease Caused by Drugs|title=Sleisenger and Fordtran's Gastrointestinal and Liver Disease|edition=Ninth|pages=1413-1446|volume=2|year=2010|veditors=Feldman M, Friedman LS, Brandt LJ|publisher=Saunders Elsevier|isbn=978-1-4160-6189-2|doi=10.1016/B978-1-4160-6189-2.00086-X}} causing hepatocellular injury.{{cite journal|vauthors=Stine JG, Lewis JH|title=Hepatotoxicity of Antibiotics: A Review and Update for the Clinician|journal=Clinics in Liver Disease|volume=17|issue=4|year=2013|pages=609-642|doi=10.1016/j.cld.2013.07.008|pmid=24099021}}

Clinical trials

Phase II Study of Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.{{cite journal | vauthors = Schutt AJ, Dalton RJ, Kovach JS, Moertel CG, O'Connell MJ | title = Phase II study of hycanthone in patients with advanced colorectal carcinoma | journal = Cancer Treatment Reports | volume = 67 | issue = 6 | pages = 593–4 | date = June 1983 | pmid = 6861166 }}
Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed){{cite web | title = Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas | url = http://www.cancer.gov/clinicaltrials/search/view?cdrid=77360&version=HealthProfessional&protocolsearchid=10235377 | archive-url = https://web.archive.org/web/20150213213104/http://www.cancer.gov/clinicaltrials/search/view?cdrid=77360&version=HealthProfessional&protocolsearchid=10235377 | archive-date = 13 February 2015 | work = U.S. National Cancer Institute }}

Physical properties

class="wikitable"
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

Category:Antiparasitic agents

Category:Thioxanthones

Category:Diethylamino compounds