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Names | |
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Preferred IUPAC name N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.003.965 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C11H14AsNO3S2 | |
Molar mass | 347.28 g·mol−1 |
Pharmacology | |
P01AR01 ( WHO ) QP51AD01 ( WHO ) | |
Oral | |
Pharmacokinetics: | |
89 % Hepatic [1] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Arsthinol (INN) is an antiprotozoal agent. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of acetarsol with 2,3-dimercaptopropanol (British anti-Lewisite) [2] and has been demonstrated to be effective against amoebiasis and yaws. It was marketed a few years later by Endo Products (Balarsen, Tablets, 0.1 g). [3]
Among trivalent organoarsenicals, arsthinol was considered very well tolerated. [4] Recently, it was studied for its anticancer activity. [5] [6]
Arsthinol has IUPAC name of N-[2-hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl] acetamide with a molecular formula of C11H14AsNO3S2 and is represented by the SMILES notation, CC(=O)NC1=C(C=CC(=C1)[As]2SCC(S2)CO)O. [7]
The molecular weight of Arsthinol is 347.3 g/mol, with a hydrogen bond donor count of 3 and a hydrogen bond acceptor count of 5. It has 3 rotatable bonds, an exact mass of 347.279 g/mol, and a monoisotopic mass of 346.963105 g/mol. The topological polar surface area is 120Ų, and the compound contains 18 heavy atoms. It has no formal charge, a complexity of 308, and contains no isotope atoms. There are no defined atom stereocenters, but there is 1 undefined atom stereocenter. The compound has no defined or undefined bond stereocenters, includes 1 covalently bonded unit, and is canonicalized. [8] [9]