Basic information
- CAS
479-50-5- Standard SMILES
CCN(CC)CCNc1ccc(C)c2sc3ccccc3c(=O)c12- InChIKey
FBQPGGIHOFZRGH-UHFFFAOYSA-N- Molecular formula
- C20H24N2OS
- Average molar mass
- 340.5 g/mol
- Monoisotopic mass
- 340.16093457
Overview
Lucanthone is a thioxanthen-9-one compound having a methyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. Formerly used for the treatment of schistosomiasis. It is a prodrug, being metabolised to hycanthone. It has a role as a mutagen, an antineoplastic agent, a schistosomicide drug, a photosensitizing agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and an adjuvant.
Names & identifiers
- Preferred name
- Lucanthone
- IUPAC
- 1-[2-(diethylamino)ethylamino]-4-methylthioxanthen-9-one
- English name
- lucanthone
- Molecular formula
- C20H24N2OS
- Molecular weight
- 340.48
Names & synonyms
LUCANTHONE479-50-5LucanthonumLucantona1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one1-((2-(diethylamino)ethyl)amino)-4-methyl-9H-thioxanthen-9-one1-{[2-(Diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-oneCHEBI:51052FC6D57000M9H-Thioxanthen-9-one, 1-((2-(diethylamino)ethyl)amino)-4-methyl-DTXSID60232301-diethylaminoethylethylamino-4-methyl-thioxanthenone
Show more names
LycanthoneLucanthone, 10 mM in DMSOAutophagy,inhibit,Lucanthone,Inhibitor1-(2-diethylaminoethylamino)-4-(methyl)thioxanthen-9-one1-[[2-(Diethylamino)ethyl]amino]-4-methyl-9H-thioxanthen-9-one
1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-one9H-Thioxanthen-9-one, 1-[[2-(diethylamino)ethyl]amino]-4-methyl-RefChem:154184DTXCID603230207-532-4LucanthonLucanthonum [INN-Latin]Lucantona [INN-Spanish]
Database identifiers
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 57.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 426
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility3.15e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 64.5 °C · 64.5°C
- Boiling point
- 512.4 · 512.4±50.0 °C(Predicted)
- Density
- 1.0915 · 1.0915 (rough estimate)
- refractive index
- 1.595 · 1.5950 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 25 mg/mL · DMSO : 25 mg/mL (73.43 mM)
- form
- Solid
- pka
- 10 · 10.00±0.25(Predicted)
- color
- Off-white to orange
- FDA UNII
- 6 D57000M · FC6D57000M
- NCI Drug Dictionary
Chemistry & industry
Pharmacology
Pharmacodynamics
Although lucanthone has structural and biochemical similarities to Actinomycin D, it has no hematological or gastro-intestinal toxicity at clinically tolerated doses. In trials, Lucanthone was found to be safe, practical and effective and was proposed for use in clinical protocols for the treatment of cancer. The specificity of lucanthone in combination with radiation for the treatment of brain tumors arises from the fact that lucanthone acts preferentially on cycling cells (most of the normal brain cells are non-cycling) and the fact that lucanthone crosses the blood brain barrier efficiently.
Mechanism of ActionRecent 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.
MeSH Pharmacological ClassificationAgents that act systemically to kill adult schistosomes.
Absorption, Distribution and ExcretionOrally available
Cellular LocationsCytoplasm
Applications
UsesLucanthone is an endonuclease inhibitor of Apurinic endonuclease-1 (APE-1).
Suppliers33 total
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
郑州汇聚化工有限公司13393710386 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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