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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 479-50-5
• PubChem SID: 160967835; 46507260
• PubChem CID: 10180

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.841316
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9962958
• LogD (pH = 7.4): 3.7037666
• Log P: 5.0165625
• Molar Refractivity: 106.0109 cm^3
• Polarizability: 39.79871 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.72
• LOG S: -5.03
• Solubility (Water): 3.15e-03 g/l

DETAILS

DrugBank - DB04967

• 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

• 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