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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 of LUCANTHONE

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

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
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
[(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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:49 UTC 2023
Edited
by admin
on Fri Dec 15 15:19:49 UTC 2023
Record UNII
FC6D57000M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LUCANTHONE
INN   MI  
INN  
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
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
Code System Code Type Description
CHEBI
51052
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
NCI_THESAURUS
C83925
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
MESH
D008154
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
DRUG CENTRAL
1616
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
EVMPD
SUB08613MIG
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023230
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-532-4
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
FDA UNII
FC6D57000M
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
PUBCHEM
10180
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
INN
337
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
SMS_ID
100000082269
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
DRUG BANK
DB04967
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL279014
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
MERCK INDEX
m6920
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY Merck Index
CAS
479-50-5
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
WIKIPEDIA
LUCANTHONE
Created by admin on Fri Dec 15 15:19:49 UTC 2023 , Edited by admin on Fri Dec 15 15:19:49 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY