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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:34 UTC
HMDB IDHMDB15607
Secondary Accession NumbersNone
Metabolite Identification
Common NameLucanthone
DescriptionLucanthone is only found in individuals that have used or taken this drug. It is 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.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.
Structure
Thumb
Synonyms
ValueSource
1-((2-(diethylamino)Ethyl)amino)-4-methylthioxanthen-9-oneChEBI
1-diethylaminoethylethylamino-4-Methyl-thioxanthenoneChEBI
1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-oneChEBI
LucanthonumChEBI
LucantonaChEBI
1-[[2-(diethylamino)Ethyl]amino]-4-methylthioxanthoneHMDB
LucanthonHMDB
Lucanthone monohydrochlorideHMDB
Chemical FormulaC20H24N2OS
Average Molecular Weight340.482
Monoisotopic Molecular Weight340.16093409
IUPAC Name1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
Traditional Namelucanthone
CAS Registry Number479-50-5
SMILES
CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(C)C=C1
InChI Identifier
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
InChI KeyInChIKey=FBQPGGIHOFZRGH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiochromenes. These are organosulfur compounds that are analogues to chromene, with the difference that a sulfur atom replaces the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiochromenes
Sub ClassNot Available
Direct ParentThiochromenes
Alternative Parents
Substituents
  • Thiochromene
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anticancer Agents
  • Radiation-Sensitizing Agents
  • Schistosomicides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.15e-03 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 mg/mLALOGPS
logP4.72ALOGPS
logP5.02ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)18.84ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.01 m3·mol-1ChemAxon
Polarizability39.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04967
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04967
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04967
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9772
KEGG Compound IDC11715
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLucanthone
NuGOwiki LinkHMDB15607
Metagene LinkHMDB15607
METLIN IDNot Available
PubChem Compound10180
PDB IDNot Available
ChEBI ID51052
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [15330152 ]
  2. Del Rowe JD, Bello J, Mitnick R, Sood B, Filippi C, Moran J, Freeman K, Mendez F, Bases R: Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone. Int J Radiat Oncol Biol Phys. 1999 Jan 1;43(1):89-93. [9989518 ]

Enzymes

General function:
Involved in DNA binding
Specific function:
Repairs oxidative DNA damages in vitro. May have a role in protection against cell lethality and suppression of mutations. Removes the blocking groups from the 3'-termini of the DNA strand breaks generated by ionizing radiations and bleomycin
Gene Name:
APEX1
Uniprot ID:
P27695
Molecular weight:
35554.2
References
  1. 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. [15330152 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. 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. [9169823 ]
  2. 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. [10487533 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]