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Arsthinol

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{{chembox | UNII_Ref = | UNII = QNT09A162Y | ImageFile = Arsthinol.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Structural formula of arsthinol | SystematicName = N-{2-Hydroxy-5-phenyl}acetamide | Section1 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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3D model (JSmol)

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| ChemSpider

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| ECHA InfoCard | 100.003.965 Edit this at Wikidata |- | EC Number

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  • 204-361-7

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| KEGG

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PubChem CID

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CompTox Dashboard (EPA)

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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

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SMILES
  • CC(=O)NC1=C(O)C=CC(=C1)1SCC(CO)S1
  • O=C(Nc2cc(1SCC(S1)CO)ccc2O)C

|- | Section2 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

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Chemical formula

| C11H14AsNO3S2

|- | Molar mass

| 347.28 g·mol

|- | Section3 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Pharmacology

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Routes of
administration

| Oral |- | colspan=2 style="text-align:left; background-color:#eaeaea;" | Pharmacokinetics: |- |-

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Metabolism

| 89 % Hepatic

|- |- }} 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) 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). Among trivalent organoarsenicals, arthinol was considered as very well tolerated . In 2006 it was studied for its antileukemic activity .

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- dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity. J Organomet Chem 691: 1081-1084
Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
Entamoeba
Tissue amebicides
Nitroimidazole derivatives
Other
Luminal amebicides
Hydroxyquinoline derivatives
Dichloroacetamide derivatives
Aminoglycoside
Other/ungrouped
Acanthamoeba
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