LUCANTHONE

US Previously Marketed

First approved in 1960

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24N2OS
Molecular Weight	340.482
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCNC1=CC=C(C)C2=C1C(=O)C3=CC=CC=C3S2

InChI

InChIKey=FBQPGGIHOFZRGH-UHFFFAOYSA-N

InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C20H24N2OS
Molecular Weight	340.482
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21935361 | https://www.ncbi.nlm.nih.gov/pubmed/9169823 | https://www.ncbi.nlm.nih.gov/pubmed/18866998 | https://adisinsight.springer.com/drugs/800016008

Lucanthone is a thioxanthenone DNA intercalator. It inhibits topoisomerases and the dual function base excision repair enzyme apurinic endonuclease 1. Lucanthone has been devised for the treatment of schistosomiasis. It is also an antitumor agent. Lucanthone was being developed by Spectrum Pharmaceuticals for the treatment of malignant brain tumours.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA-(apurinic or apyrimidinic site) lyase 8 Target ID: CHEMBL5619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25280182\|https://www.ncbi.nlm.nih.gov/pubmed/25131339\|http://drugcentral.org/drugcard/1616\|https://www.ncbi.nlm.nih.gov/pubmed/21935361	Inhibitor 8297		5.0 µM [IC50]
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9169823\|https://www.ncbi.nlm.nih.gov/pubmed/10487533	Inhibitor 8297

AUC

Value	Dose	Co-administered	Analyte	Population
96 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9989518/	10 mg/kg 1 times / 2 days steady-state, oral dose: 10 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		LUCANTHONE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51052	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51052
MolPort	MolPort-006-111-398	https://www.molport.com/shop/molecule-link/MolPort-006-111-398
ZINC	ZINC000003831012	http://zinc15.docking.org/substances/ZINC000003831012

PubMed

Title	Date	PubMed
Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone.	1999 Jan 1	9989518
Abasic sites in DNA of HeLa cells induced by lucanthone.	2002	12449731
Radiation resistance in glioma cells determined by DNA damage repair activity of Ape1/Ref-1.	2010	20679741
[(1,2,5,6-η)-1,5-Cyclo-octa-diene](1-isopropyl-3-methyl-imidazolin-2-yl-idene)(triphenyl-phosphine)iridium(I) tetra-fluorido-borate dichloro-methane solvate.	2010 Aug 18	21588520
4-(Piperidin-1-yl)-4H-benzo[b]tetra-zolo[1,5-d][1,4]diazepin-5(6H)-one.	2010 Dec 4	21522729
2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1,3(2H)-dione.	2010 Feb 13	21580382
2-Propyl 3,3-dibromo-2-hydroxy-pyrrolidine-1-carboxyl-ate.	2010 Feb 13	21580358

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:19:49 GMT 2023` Edited by `admin` on `Fri Dec 15 15:19:49 GMT 2023`
Record UNII	FC6D57000M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUCANTHONE

Official Name

English

1-(2-DIETHYLAMINOETHYLAMINO)-4-METHYLTHIAXANTHONE

Systematic Name

English

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

Systematic Name

English

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

Systematic Name

English

LUCANTHONE [MI]

Common Name

English

lucanthone [INN]

Common Name

English

1-((2-(DIETHYLAMINO)ETHYL)AMINO)-4-METHYLTHIOXANTHEN-9-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C250