CANTHIN-6-ONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H8N2O
Molecular Weight	220.2261
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1C=CC2=C3N1C4=CC=CC=C4C3=CC=N2

InChI

InChIKey=ZERVJPYNQLONEK-UHFFFAOYSA-N

InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28161479 | https://www.ncbi.nlm.nih.gov/pubmed/21134431 | https://www.ncbi.nlm.nih.gov/pubmed/16949231 | https://www.ncbi.nlm.nih.gov/pubmed/12820240

Canthin-6-one is a natural product isolated from various plant genera and from fungi with potential antitumor activity. It induces cell death, cell cycle arrest and differentiation in human myeloid leukemia cells. Canthin-6-one is main compound isolated from Zanthoxylum chiloperone var angustifolium with broad spectrum antifungal, leishmanicidal and trypanocidal activities. Canthin-6-one exhibited trypanocidal activity in vivo in the mouse model of acute or chronic infection. Canthin-6-one exhibited a broad spectrum of activities against Aspergillus fumigatus, A. niger, A. terreus, Candida albicans, C. tropicalis, C. glabrata, Cryptococcus neoformans, Geotrichum candidum, Saccharomyces cerevisiae, Trichosporon beigelii, Trichosporon cutaneum and Trichophyton mentagrophytes var. interdigitale with MICs values between 5.3 and 46 umol/L.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25379743	Activator 1447
Leishmania sp. 3 Target ID: CHEMBL612241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12007711	Inhibitor 8504
Trypanosoma cruzi 12 Target ID: CHEMBL368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949231	Inhibitor 8504
Candida albicans 14 Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820240	Inhibitor 8504
Cryptococcus neoformans var. neoformans 2 Target ID: CHEMBL2367317 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820240	Inhibitor 8504
Trichosporon beigelii 1 Target ID: CHEMBL612874 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820240	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Leukemia 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28161479	Primary	Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25379743 https://www.ncbi.nlm.nih.gov/pubmed/25348942	Primary	Basic research	Unknown Approved Use Unknown
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12007711	Primary	Preclinical	Unknown Approved Use Unknown
Chagas disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949231	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.	2005-11	16309303
Antifungal compounds from Zanthoxylum chiloperone var. angustifolium.	2003-06	12820240

Patents

Sample Use Guides

In Vivo Use Guide

The mice were treated for 5 weeks postinfection with Canthin-6-one by oral (14 days) or intralesional route (4 days) at 10 mg/kg daily.

Route of Administration: Other

In Vitro Use Guide

Canthin-6-one induced cell cycle arrest at G0/G1 (7uM) and G2 (45uM) evidenced by DNA content, BrdU incorporation and cyclin B1/histone 3 quantification in Kasumi-1 human myeloid leukemia cells.

Name

Type

Language

NSC-103003

Preferred Name

English

CANTHIN-6-ONE

Common Name

English

6H-INDOLO(3,2,1-DE)(1,5)NAPHTHYRIDIN-6-ONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

97176