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Lucanthone

Lucanthone structure

CAS No:
479-50-5
Formula:
C20H24N2OS
Chemical Name:
Lucanthone
Synonyms:
9H-Thioxanthen-9-one,1-[[2-(diethylamino)ethyl]amino]-4-methyl-;Thioxanthen-9-one,1-[[2-(diethylamino)ethyl]amino]-4-methyl-;1-[[2-(Diethylamino)ethyl]amino]-4-methyl-9H-thioxanthen-9-one;1-(2-Diethylaminoethylamino)-4-methylthiaxanthen-9-one;Lucanthone;NSC 20530
Categories:
Organic Chemistry > Heterocyclic Ring

Description

Lucanthone is an endonuclease inhibitor of Apurinic endonuclease-1 (APE-1).

Solid

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 schistosomicide drug, an antineoplastic agent, a photosensitizing agent, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, a prodrug, an adjuvant and a mutagen.|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.|Lucanthone is an orally available thioxanthone-based DNA intercalator and inhibitor of the DNA repair enzyme apurinic-apyrimidinic endonuclease 1 (APEX1 or APE1), with anti-schistosomal and potential antineoplastic activity. Lucanthone intercalates DNA and interferes with the activity of topoisomerases I and II during replication and transcription, thereby inhibiting the synthesis of macromolecules. In addition, this agent specifically inhibits the endonuclease activity of APE1, without affecting its redox activity, resulting in un-repaired DNA strand breaks which may induce apoptosis. Therefore, lucanthone may sensitize tumor cells to radiation and chemotherapy. Furthermore, lucanthone inhibits autophagy through the disruption of lysosomal function. The multifunctional nuclease APE1 is a key component for DNA repair; its expression is often correlated with tumor cell resistance to radio- and chemotherapy.|One of the SCHISTOSOMICIDES, it has been replaced largely by HYCANTHONE and more recently PRAZIQUANTEL. (From Martindale The Extrapharmacopoeia, 30th ed., p46)

Lucanthone Basic Attributes

Molecular Weight：

340.485

Exact Mass：

340.48

EC Number：

207-532-4

UNII：

FC6D57000M

DSSTox ID：

DTXSID6023230

NCI Thesaurus Code：

C83925

Characteristics

PSA：

57.6

XLogP3：

4.54980

Appearance：

Solid

Density：

1.184g/cm3

Melting Point：

64-65 °C @ Solvent: Ethanol

Boiling Point：

512.4ºC at 760 mmHg

Flash Point：

263.7ºC

Refractive Index：

1.638

Water Solubility：

3.15e-03 g/L

Drug Information

Drug Indication：

Intended for use as a radiation sensitizer in the treatment of brain cancer.

Pharmacology：

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.

MeSH：

Agents that act systemically to kill adult schistosomes. (See all compounds classified as Schistosomicides.)

Absorption：

Orally available

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.

MeSH Entry Terms：

Lucanthone

Computed Properties

Molecular Weight:340.5
XLogP3:4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:340.16093457
Monoisotopic Mass:340.16093457
Topological Polar Surface Area:57.6
Heavy Atom Count:24
Complexity:426
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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lucanthone

CAS No.: 479-50-5

Grade: Industrial Grade

Content: 99%

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