Arsthinol
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457817818 | ImageFile = Arsthinol.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Structural formula of arsthinol | SystematicName = N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide |Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers
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| ECHA InfoCard | 100.003.965 |- | EC Number
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- 204-361-7
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- 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
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- CC(=O)NC1=C(O)C=CC(=C1)[As]1SCC(CO)S1
- O=C(Nc2cc([As]1SCC(S1)CO)ccc2O)C
|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Properties
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| C11H14AsNO3S2
|- | Molar mass
| 347.28 g·mol−1
|- |Section6=! colspan=2 style="background: #f8eaba; text-align: center;" |Pharmacology
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| P01AR01 (WHO) QP51AD01 (WHO) |-
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| Oral |- | colspan=2 style="text-align:left; background-color:#eaeaea;" | Pharmacokinetics: |- |-
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| 89 % Hepatic[1]
|- |- }} 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
- ^ 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 EAH. (1949) A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical. Am J Trop Med Hyg s1-29: 185
- ^ 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: 360-363
- ^ 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
- ^ 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
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