U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of LUCANTHONE HYDROCHLORIDE

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
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.

Approval Year

AUC

AUC

ValueDoseCo-administeredAnalytePopulation
96 μg × h/mL
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
PubMed

PubMed

TitleDatePubMed
Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone.
1999 Jan 1
Abasic sites in DNA of HeLa cells induced by lucanthone.
2002
Design of small volume HX and triple-resonance probes for improved limits of detection in protein NMR experiments.
2003 Sep
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
Clonogenicity of human leukemic cells protected from cell-lethal agents by heat shock protein 70.
2005 Spring
The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target.
2007 Jun-Aug
Radiation resistance in glioma cells determined by DNA damage repair activity of Ape1/Ref-1.
2010
[(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
4-(Piperidin-1-yl)-4H-benzo[b]tetra-zolo[1,5-d][1,4]diazepin-5(6H)-one.
2010 Dec 4
2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1,3(2H)-dione.
2010 Feb 13
2-Propyl 3,3-dibromo-2-hydroxy-pyrrolidine-1-carboxyl-ate.
2010 Feb 13
Lucanthone is a novel inhibitor of autophagy that induces cathepsin D-mediated apoptosis.
2011 Feb 25
Name Type Language
LUCANTHONE HYDROCHLORIDE
HSDB   MI   USAN  
USAN  
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
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
Code System Code Type Description
MERCK INDEX
m6920
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY Merck Index
NSC
14574
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
HSDB
7095
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID20878506
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
FDA UNII
918K9N56QZ
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL279014
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
CAS
548-57-2
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
NCI_THESAURUS
C76055
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
PUBCHEM
11054
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
DRUG BANK
DBSALT000826
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-951-5
Created by admin on Fri Dec 15 15:12:55 GMT 2023 , Edited by admin on Fri Dec 15 15:12:55 GMT 2023
PRIMARY