DT-Web

DB04967 - Lucanthone


Identification
Name Lucanthone
Accession Number DB04967
Type small molecule
Description One of the schistosomicides, it has been replaced largely by hycanthone and more recently praziquantel. (From Martindale The Extrapharmacopoeia, 30th ed., p46). It is currently being tested as a radiation sensitizer.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 340.482
Groups approved
Monoisotopic Weight 340.16093409
Pharmacology
Indication Intended for use as a radiation sensitizer in the treatment of brain cancer.
Mechanism of action Recent data suggests that lucanthone inhibits post-radiation DNA repair in tumor cells. The ability of lucanthone to inhibit AP endonuclease and topoisomerase II probably account for the specific DNA repair inhibition in irradiated cells.
Absorption Orally available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


DNA topoisomerase 2-alpha
Name DNA topoisomerase 2-alpha
Gene Name TOP2A
Pharmacological action yes
Actions inhibitor
References
  • Bases RE, Mendez F: Topoisomerase inhibition by lucanthone, an adjuvant in radiation therapy. Int J Radiat Oncol Biol Phys. 1997 Mar 15;37(5):1133-7. - Pubmed
  • Dassonneville L, Bailly C: Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.6031
DNA-(apurinic or apyrimidinic site) lyase
Name DNA-(apurinic or apyrimidinic site) lyase
Gene Name APEX1
Pharmacological action yes
Actions inhibitor
References
  • Luo M, Kelley MR: Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. - Pubmed
DTHybrid score 0.806
DNA
Name DNA
Gene Name Not Available
Pharmacological action yes
Actions intercalation
References
  • Milligan AJ, Metz JA, Leeper DB: The effect of lucanthone on sublethal radiation damage, in vivo. Int J Radiat Oncol Biol Phys. 1984 Dec;10(12):2309-13. - Pubmed
  • Bailly C, Waring MJ: Preferential intercalation at AT sequences in DNA by lucanthone, hycanthone, and indazole analogs. A footprinting study. Biochemistry. 1993 Jun 15;32(23):5985-93. - Pubmed
  • Dassonneville L, Bailly C: Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. - Pubmed
DTHybrid score Not Available
DNA topoisomerase 1
Name DNA topoisomerase 1
Gene Name TOP1
Pharmacological action yes
Actions inhibitor
References
  • Bases RE, Mendez F: Topoisomerase inhibition by lucanthone, an adjuvant in radiation therapy. Int J Radiat Oncol Biol Phys. 1997 Mar 15;37(5):1133-7. - Pubmed
  • Dassonneville L, Bailly C: Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. - Pubmed
DTHybrid score 1.3671

Predictions


Id Partner name Gene Name Score
3552 DNA topoisomerase 1 topA 1.3671
477 DNA topoisomerase 4 subunit A parC 0.1361
886 DNA topoisomerase 4 subunit A parC 0.1361
6226 DNA topoisomerase 4 subunit A parC 0.1361
404 DNA gyrase subunit A gyrA 0.1336
6224 DNA gyrase subunit A gyrA 0.1336
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0797
1588 Multidrug resistance protein 1 ABCB1 0.0759
102 DNA topoisomerase I, mitochondrial TOP1MT 0.0647
4192 DNA topoisomerase 2-beta TOP2B 0.044
862 Multidrug resistance-associated protein 1 ABCC1 0.0438
4512 Cytochrome P450 3A4 CYP3A4 0.0418
4200 Cytochrome P450 1A2 CYP1A2 0.0389
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0278
118 Organic cation/carnitine transporter 2 SLC22A5 0.0211
4118 Cytochrome P450 3A5 CYP3A5 0.0198
588 Chromodomain-helicase-DNA-binding protein 1 CHD1 0.0192
6137 Multidrug resistance-associated protein 6 ABCC6 0.0163
4119 Cytochrome P450 2D6 CYP2D6 0.015
2539 Tubulin alpha-1 chain TUBA4A 0.0126
6107 Cytochrome P450 3A7 CYP3A7 0.0124
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.012
161 Tubulin beta chain TUBB 0.0117
312 Tubulin beta chain TUB2 0.0117
723 Cytosolic phospholipase A2 PLA2G4A 0.0114
4757 Cytochrome P450 2C9 CYP2C9 0.0112
1729 Solute carrier family 22 member 6 SLC22A6 0.0107
1898 Cytochrome P450 1B1 CYP1B1 0.0105
6016 Cytochrome P450 2C19 CYP2C19 0.0103
833 Organic cation/carnitine transporter 1 SLC22A4 0.0099
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0094
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0089
4604 Liver carboxylesterase 1 CES1 0.0086
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0076
6148 Multidrug resistance-associated protein 7 ABCC10 0.0075
6147 Solute carrier family 22 member 3 SLC22A3 0.007
6030 Cytochrome P450 2B6 CYP2B6 0.0067
6144 Solute carrier family 22 member 2 SLC22A2 0.0066
6013 Cytochrome P450 2E1 CYP2E1 0.0065
3923 Cholinesterase BCHE 0.0065
992 Protein tyrosine kinase 2 beta PTK2B 0.0064
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0064
587 Serum albumin ALB 0.0055
6024 Cytochrome P450 1A1 CYP1A1 0.0053
4120 NADPH--cytochrome P450 reductase POR 0.0053
3947 Xanthine dehydrogenase/oxidase XDH 0.0045
6228 Nuclear receptor coactivator 1 NCOA1 0.0044
6241 Nuclear receptor coactivator 2 NCOA2 0.0043
869 Estrogen receptor beta ESR2 0.0041
776 Bile salt export pump ABCB11 0.0041
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.004
373 Transthyretin TTR 0.0038
6172 ATP-binding cassette sub-family B member 8, mitochondrial ABCB8 0.0036
136 Estrogen receptor ESR1 0.0035
5718 Cytochrome P450 2A6 CYP2A6 0.0034
908 Glutathione S-transferase theta-1 GSTT1 0.0032
337 NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial NDUFS7 0.0029
214 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial NDUFS3 0.0029
803 NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NDUFS2 0.0029
6168 Solute carrier family 22 member 16 SLC22A16 0.0029
6861 Alcohol dehydrogenase [NADP+] AKR1A1 0.0026
904 Glutathione S-transferase P GSTP1 0.0025
5251 Carbonyl reductase [NADPH] 1 CBR1 0.0022
650 Aldo-keto reductase family 1 member C3 AKR1C3 0.0021
290 Prostaglandin G/H synthase 2 PTGS2 0.002
20 Prostaglandin G/H synthase 1 PTGS1 0.0019
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.0019
76 Nitric-oxide synthase, brain NOS1 0.0018
4924 Cytochrome P450 2C8 CYP2C8 0.0016
7 Nitric oxide synthase, inducible NOS2 0.0016
291 Nitric-oxide synthase, endothelial NOS3 0.0015
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