Arsthinol

Arsthinol

Names
Systematic IUPAC name N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide
Identifiers
CAS Number	119-96-0
ChemSpider	8107
EC Number	204-361-7
Jmol interactive 3D	Image Image
KEGG	D07356
PubChem	8414
UNII	QNT09A162Y
InChI InChI=1S/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15) Key: MRUDSZSRLQAPOG-UHFFFAOYSA-N InChI=1/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15) Key: MRUDSZSRLQAPOG-UHFFFAOYAP
SMILES CC(=O)NC1=C(O)C=CC(=C1)[As]1SCC(CO)S1 O=C(Nc2cc([As]1SCC(S1)CO)ccc2O)C
Properties
Chemical formula	C11H14AsNO3S2
Molar mass	347.28 g·mol^−1
Pharmacology
ATC code	P01AR01 QP51AD01
Routes of administration	Oral
Pharmacokinetics:
Metabolism	89 % Hepatic[1]
Except where otherwise noted, data are 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 later 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