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{{short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| IUPAC_name = 1-(2-diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone |
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| Watchedfields = changed |
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| image = Hycanthone.png |
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| verifiedrevid = 407389823 |
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| CAS_number = 3105-97-3 |
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| IUPAC_name = 1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone |
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| ATC_prefix = none |
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| image = Hycanthone.png |
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| ATC_suffix = |
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| PubChem = 3634 |
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<!--Clinical data--> |
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| DrugBank = |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 3105-97-3 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 3634 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 2BXX5EVN2A |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 52768 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00541 |
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| KEGG = D00541 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| chemical_formula = |
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| ChEMBL = 22077 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID =3508 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MFZWMTSUNYWVBU-UHFFFAOYSA-N |
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<!--Chemical data--> |
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| chemical_formula = |
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| C=20 | H=24 | N=2 | O=2 | S=1 |
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| C=20 | H=24 | N=2 | O=2 | S=1 |
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| smiles = CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O |
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| molecular_weight = 356.48 g/mol |
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| smiles = CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Hycanthone''' is the ] approved by the FDA in 1975. It is a metabolite of ]. Hycanthone interferes with ] nerve function, resulting in ] and death. This agent also intercalates into DNA and inhibits RNA synthesis '']'' and shows potential ] activity.<ref>{{cite web | title = hycanthone | url = http://www.cancer.gov/drugdictionary?cdrid=39477 | work = NCI Cancer Dictionary }}</ref> |
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'''Hycanthone''' is a ]. It is a metabolite of ]. |
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==Anti-schistosomal activity== |
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Hycanthone is shown to be an effective inhibitor of ] (AChE) from '']'', 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.<ref>{{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 }}</ref> |
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Hycanthone is shown to ] into DNA and inhibit RNA synthesis '']''. A growing body of evidence has shown that hycathone has an ] activity.{{cn|date=December 2022}} |
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==Toxicity== |
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Hycanthone is a dose-dependent ],<ref>{{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}}</ref> causing hepatocellular injury.<ref>{{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}}</ref> |
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==Clinical trials== |
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* Phase II Study of Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.<ref name="pmid6861166">{{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 }}</ref> |
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* Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)<ref>{{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 }}</ref> |
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==Physical properties== |
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{| class="wikitable" |
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| ''']''' || Solid |
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| ''']''' || Soluble in ethanol, methanol, DMSO, and water |
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| ''']''' || 233, 258, 329, 438 nm |
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| ''']''' || 173-176 °C |
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| ''']''' || 3.74 |
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== References == |
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{{reflist}} |
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{{pharma-stub}} |
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{{Anthelmintics}} |
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] |
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] |
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] |
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] |
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] |