HYCANTHONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24N2O2S
Molecular Weight	356.482
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCNC1=CC=C(CO)C2=C1C(=O)C3=C(S2)C=CC=C3

InChI

InChIKey=MFZWMTSUNYWVBU-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/hycanthone | https://www.ncbi.nlm.nih.gov/pubmed/1720380 | https://www.ncbi.nlm.nih.gov/pubmed/1206768 | https://www.ncbi.nlm.nih.gov/pubmed/8270443 | https://www.ncbi.nlm.nih.gov/pubmed/1190369 | https://www.ncbi.nlm.nih.gov/pubmed/7229816 | https://www.ncbi.nlm.nih.gov/pubmed/21935361

Hycanthone is a thioxanthene derivative of lucanthone with anti-schistosomal activity and potential antineoplastic activity. It was clinically available for the treatment of human schistosomiasis. Anti-helmintic action relies on its ability to inhibit worm monoamine oxidase and cholinesterases. Hycanthone produced immediate side effects such as hepatotoxicity and gastrointestinal disturbances, and was consequently withdrawn. Hycanthone inhibits apurinic endonuclease-1 (APE1) by direct protein binding. Hycanthone was used in the 1980s as antitumor agents, it was pulled out of Phase II trials.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
UniProtKB: Q71SU7 (Carboxylic ester hydrolase) 4 Target ID: UniProtKB: Q71SU7 (Carboxylic ester hydrolase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1190369 \| https://www.ncbi.nlm.nih.gov/pubmed/7229816	Inhibitor 8297
monoamine oxidase activity 6 Target ID: GO:0097621 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7229816	Inhibitor 8297
DNA-(apurinic or apyrimidinic site) lyase 8 Target ID: CHEMBL5619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21935361	Inhibitor 8297	80.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schistosomiasis 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1206768	Curative		Withdrawn	Hycanthone Approved Use human schistosomiasis
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8270443 https://www.ncbi.nlm.nih.gov/pubmed/356976 https://www.cancer.gov/publications/dictionaries/cancer-drug/def/hycanthone	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BIB0	https://www.1pchem.com/search?query=1P00BIB0
Ambeed	A204944	http://www.ambeed.com/search/Search.html?keyword=A204944
AstaTech	C74594	http://astatechinc.com/CPSResult.php?CRNO=C74594
BLD Pharm	BD55249	http://www.bldpharm.com/search/Search.html?keyword=BD55249
BOC Sciences	3105-97-3	http://www.bocsci.com/description.asp?cas=3105-97-3
Chem Scene	CS-4690	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4690
Fluorochem	541743	http://www.fluorochem.co.uk/Products/Product?code=541743
Hairui	HR138995	http://www.hairuichem.com/en/product/search.do?q=HR138995
KeyOrganics	DS-12960	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-12960
Lab Network	LN01343044	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343044
MedChem Express	HY-B1099	https://www.medchemexpress.com/search.html?q=HY-B1099&ft=&fa=&fp=
MolPort	MolPort-003-665-576	https://www.molport.com/shop/molecule-link/MolPort-003-665-576
MuseChem	I007230	https://www.musechem.com/product/I007230.html
Tetrahedron	TS79357	http://www.thsci.com/search.do?q=TS79357
Toronto Research Chemicals	H674305	https://www.trc-canada.com/product-detail/?CatNum=H674305
eMolecules	33507342	https://orderbb.emolecules.com/search/#?query=33507342
eNovation Chemicals	D114144	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D114144&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7999395699	https://mcule.com/MCULE-7999395699/

PubMed

Title	Date	PubMed
Long-term hepatocellular effects of hycanthone and of two other anti-Schistosomal drugs in mice infected with Schistosoma mansoni.	1976 Jun	180276
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
The NIH-NIAID schistosomiasis resource center.	2008 Jul 30	18665228
Mefloquine--an aminoalcohol with promising antischistosomal properties in mice.	2009	19125172
Reduced susceptibility to praziquantel among naturally occurring Kenyan isolates of Schistosoma mansoni.	2009 Aug 18	19688043
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.	2009 Jul 14	19597541
RNA interference in Schistosoma mansoni schistosomula: selectivity, sensitivity and operation for larger-scale screening.	2010 Oct 19	20976050
Identification of novel p53 pathway activating small-molecule compounds reveals unexpected similarities with known therapeutic agents.	2010 Sep 27	20885994
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

Human schistosomiasis: single intramuscular dose (3.0, 2.5, 2.0, 1.5, and 1.0 mg/kg body weight).Unresectable pancreatic cancer: hycanthone was administered 60 mg/m2 intravenously within 2 to 4 hr during each day of the 5-day course of infusions during the first and fifth weeks of radiation therapy.

Route of Administration: Other

In Vitro Use Guide

Hycanthone stimulates motor activity of Schistosoma mansoni at concentrations of 10(-6) to 10(-5) M, and partially blocks the paralytic effects of carbachol and physostigmine.

Name

Type

Language

HYCANTHONE

Official Name

English

WIN 24,933

Code

English

HYCANTHONE [MART.]

Common Name

English

HYCANTHONE [MI]

Common Name

English

WIN-24933

Code

English

9H-THIOXANTHEN-9-ONE, 1-((2-(DIETHYLAMINO)ETHYL)AMINO)-4-(HYDROXYMETHYL)-

Systematic Name

English

HYCANTHONE [USAN]

Common Name

English

hycanthone [INN]

Common Name

English

NSC-142982

Code

English

1-[[2-(Diethylamino)ethyl]amino]-4-(hydroxymethyl)thioxanthen-9-one

Systematic Name

English

NSC-134434

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C250