Structure via PubChem · Public domain (PubChem)
lucanthone
Sign in to saveAlso known as 1-diethylaminoethylethylamino-4-methyl-thioxanthenone, 1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-one, 1-((2-(Diethylamino)ethyl)amino)-4-methylthioxanthen-9-one, Lucanthonum, Lucantona
Lucanthone (Miracil D, Myracyl D) is a drug used to treat parasitic diseases such as schistosomiasis, which was invented in 1938 by Hans Mauss and colleagues at Bayer AG. It is a prodrug and is converted to the active metabolite hycanthone. It is no longer commonly used in humans due to hepatotoxicity, especially after the subsequent development of safer drugs with similar efficacy such as praziquantel.
Chemical data
- Formula
- C20H24N2OS
- Molecular weight
- 340.5 g/mol
- IUPAC name
- 1-[2-(diethylamino)ethylamino]-4-methylthioxanthen-9-one
- SMILES
- CCN(CC)CCNC1=C2C(=C(C=C1)C)SC3=CC=CC=C3C2=O
- InChIKey
- FBQPGGIHOFZRGH-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 57.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
329 papersvia PubMed
Wikidata facts
- Mass
- 340.160934
- Has use
- medication
Show 4 more facts
- Commons category
- Lucanthone
- World Health Organisation international non-proprietary name
- lucanthone
- chemical formula
- C₂₀H₂₄N₂OS
- canonical SMILES
- CCN(CC)CCNC1=C2C(=C(C=C1)C)SC3=CC=CC=C3C2=O
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Mechanism of action
- Research
- Synthesis
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443927477 | IUPAC_name = 1-{[2-(diethylamino)ethyl]amino}-4-methyl-9H-thioxanthen-9-one | image = Lucanthone.png | image_class = skin-invert-image | width = 150 | image2 = Lucanthone molecule ball.png | image_class2 = bg-transparent | width2 = 220 | alt2 = Ball-and-stick model of the lucanthone molecule
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “lucanthone” article, available under the CC BY-SA 4.0 licence.