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479-50-5 molecular structure
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1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one

ChemBase ID: 4403
Molecular Formular: C20H24N2OS
Molecular Mass: 340.48236
Monoisotopic Mass: 340.1609344
SMILES and InChIs

SMILES:
s1c2c(c(NCCN(CC)CC)ccc2C)c(=O)c2c1cccc2
Canonical SMILES:
CCN(CCNc1ccc(c2c1c(=O)c1c(s2)cccc1)C)CC
InChI:
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
InChIKey:
FBQPGGIHOFZRGH-UHFFFAOYSA-N

Cite this record

CBID:4403 http://www.chembase.cn/molecule-4403.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one
IUPAC Traditional name
lucanthone
Brand Name
Nilodin
Miracil D
Scapuren
Tixantone
Miracol
Synonyms
Lucantona [inn-spanish]
Lucanthonum [inn-latin]
Lucanthone monohydrochloride
Lucanthone hydrochloride
Lucanthon
1-[[2-(Diethylamino)ethyl]amino]-4-methylthioxanthone
1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one
lucanthone
Lucanthone
CAS Number
479-50-5
PubChem SID
46507260
160967835
PubChem CID
10180

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB04967 external link
PubChem 10180 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 18.841316  H Acceptors
H Donor LogD (pH = 5.5) 1.9962958 
LogD (pH = 7.4) 3.7037666  Log P 5.0165625 
Molar Refractivity 106.0109 cm3 Polarizability 39.79871 Å3
Polar Surface Area 32.34 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.72  LOG S -5.03 
Solubility (Water) 3.15e-03 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB04967 external link
Item Information
Drug Groups approved; investigational
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.
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.
Affected Organisms
Humans and other mammals
Absorption Orally available
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]
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]
External Links
Wikipedia

REFERENCES

REFERENCES

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  • • 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
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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