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Lucanthone

July 24, 2017
Common Name

Lucanthone Description

Lucanthone 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 Lucanthone hydrochlorideMeSH TixantoneMeSH Miracil DMeSH

Chemical Formlia

C20H24N2OS Average Molecliar Weight

340.482 Monoisotopic Molecliar Weight

340.16093409 IUPAC Name

1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one Traditional Name

lucanthone CAS Registry Number

479-50-5 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 Key

FBQPGGIHOFZRGH-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as thiochromenes. These are organoslifur compounds that are analogues to chromene, with the difference that a slifur atom replaces the oxygen atom. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Thiochromenes Sub Class

Not Available Direct Parent

Thiochromenes Alternative Parents

  • 1-benzothiopyrans
  • Secondary alkylarylamines
  • Benzenoids
  • Vinylogous amides
  • Heteroaromatic compounds
  • Trialkylamines
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Thiochromene
  • Benzothiopyran
  • 1-benzothiopyran
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • thioxanthenes (CHEBI:51052 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticancer Agents
  • Radiation-Sensitizing Agents
  • Schistosomicides

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility3.15e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04967

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04967

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04967 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    9772 KEGG Compound ID

    C11715 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Lucanthone NuGOwiki Link

    HMDB15607 Metagene Link

    HMDB15607 METLIN ID

    Not Available PubChem Compound

    10180 PDB ID

    Not Available ChEBI ID

    51052

    Product: SGI-1028

    References Synthesis Reference Not 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10487533 ]
    3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 2384136

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