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
3D model (Jmol)	Interactive image Interactive image
ChemSpider	8107
ECHA InfoCard	100.003.965
EC Number	204-361-7
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 (WHO) QP51AD01 (WHO)
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, 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.
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. doi:10.1001/jama.1956.02960400018005.
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. doi:10.1016/j.jorganchem.2005.11.007.
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. 85: 560–568. doi:10.1016/j.ejpb.2013.06.021.