Arsthinol
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Preferred IUPAC name N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide | |
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ECHA InfoCard | 100.003.965 ![]() |
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Properties | |
Chemical formula | C11H14AsNO3S2 |
Molar mass | 347.28 g·mol−1 |
Pharmacology | |
P01AR01 (WHO) QP51AD01 (WHO) | |
Routes of administration | Oral |
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Metabolism | 89 % Hepatic[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Chemical compound
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]
References
- ^ Cristau, B; Chabas, ME; Placidi, M (1975). "Voies et cinétiques d'excrétion de l'arsenic chez le Cobaye après injection de divers médicaments organo-arséniés". Ann Pharm Fr. 33: 577–89.
- ^ Friedheim, Ernst AH (1949). "A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical". Am J Trop Med Hyg. s1-29 (2): 185–188. doi:10.4269/ajtmh.1949.s1-29.185. PMID 18116845.
- ^ Anonyme (1953). "New and nonofficial remedies; arsthinol". J Am Med Assoc. 152: 531.
- ^ Brown, CH; Gebhart, WF; Reich, A (1956). "Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen)". JAMA. 160 (5): 360–363. doi:10.1001/jama.1956.02960400018005. PMID 13278204.
- ^ Gibaud, S; Alfonsi, R; Mutzenhardt, P; et al. (2006). "(2-Phenyl-[1, 3, 2] dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity". J Organomet Chem. 691 (5): 1081–1084. doi:10.1016/j.jorganchem.2005.11.007.
- ^ Becherirat, S.; Lanhers, M.-C.; Socha, M.; Yemloul, M.; Astier, A.; Loboda, C.; Aniceto, N.; Gibaud, S. (2013). "The antitumor effects of an arsthinol-cyclodextrin complex in an heterotopic mouse model of glioma" (PDF). Eur J Pharm Biopharm. 85 (3): 560–568. doi:10.1016/j.ejpb.2013.06.021. PMID 23831266.
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Tissue amebicides |
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Luminal amebicides |
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Other/ungrouped |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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