Arsthinol

Arsthinol
Names
Systematic IUPAC name
N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide
Identifiers
ATC code P01AR01
QP51AD01
119-96-0 
ChemSpider 8107 Yes
EC number 204-361-7
Jmol-3D images Image
Image
KEGG D07356 Yes
PubChem 8414
Properties
Molecular formula
C11H14AsNO3S2
Molar mass 347.29 g·mol−1
Pharmacology
Oral
Metabolism 89 % Hepatic[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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 few years latter by Endo Products (Balarsen, Tablets, 0.1 g).[3] Among trivalent organoarsenicals, arthinol was considered as very well tolerated.[4] Recently, it was studied for its anticancer activity.[5][6]


References

  1. 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
  2. Friedheim EAH. (1949) A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical. Am J Trop Med Hyg s1-29: 185
  3. Anonyme. (1953) New and nonofficial remedies; arsthinol. J Am Med Assoc 152: 531
  4. Brown CH, Gebhart WF, Reich A. (1956) Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen). JAMA 160: 360-363
  5. 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: 1081-1084
  6. 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. Eur J Pharm Biopharm, doi: http://dx.doi.org/10.1016/j.ejpb.2013.06.021