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 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
- ^ 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.
- ^ 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. doi:10.1001/jama.1956.02960400018005.
- ^ 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.
{{cite journal}}: Explicit use of et al. in:|last4=(help) - ^ 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.
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