LUCANTHONE HYDROCHLORIDE

US Previously Marketed

First approved in 1960

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24N2OS.ClH
Molecular Weight	376.943
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LAOOXBLMIJHMFO-UHFFFAOYSA-N

InChI=1S/C20H24N2OS.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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
Design of small volume HX and triple-resonance probes for improved limits of detection in protein NMR experiments.	2003 Sep	12932464
Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone.	2004 Jul-Aug	15330152
Clonogenicity of human leukemic cells protected from cell-lethal agents by heat shock protein 70.	2005 Spring	15832946
The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target.	2007 Jun-Aug	17560642
[(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
Lucanthone is a novel inhibitor of autophagy that induces cathepsin D-mediated apoptosis.	2011 Feb 25	21148553

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:12:55 UTC 2023` Edited by `admin` on `Fri Dec 15 15:12:55 UTC 2023`
Record UNII	918K9N56QZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUCANTHONE HYDROCHLORIDE

Official Name

English

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

Common Name

English

MIRACIL D

Brand Name

English

MS-752

Code

English

MIRACOL

Brand Name

English

TIXANTONE

Brand Name

English

LUCANTHONE HYDROCHLORIDE [MI]

Common Name

English

RP-3735

Code

English

1-(2-DIETHYLAMINOETHYLAMINO)-4-METHYLTHIAXANTHONE HYDROCHLORIDE

Systematic Name

English

1-[[2-(Diethylamino)ethyl]amino]-4-methylthioxanthen-9-one monohydrochloride

Systematic Name

English

NSC-14574

Code

English

LUCANTHONE HCL

Common Name

English

79 T61

Code

English

LUCANTHONE HYDROCHLORIDE [HSDB]

Common Name

English

79-T61

Code

English

LUCANTHONE HYDROCHLORIDE [USAN]

Common Name

English

NILODIN

Brand Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471