Arsthinol

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title: "Arsthinol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiprotozoal-agents", "acetanilides", "hydroxymethyl-compounds", "phenols", "organoarsenic-dithiolates", "arsenic-heterocycles", "arsenic(iii)-compounds", "sulfur-heterocycles", "heterocyclic-compounds-with-1-ring"] topic_path: "general/antiprotozoal-agents" source: "https://en.wikipedia.org/wiki/Arsthinol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457817818 | ImageFile = Arsthinol.svg | ImageClass = skin-invert-image | ImageFile_Ref = | ImageSize = 244 | ImageName = Structural formula of arsthinol | PIN = N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide |Section1={{Chembox Identifiers | CASNo = 119-96-0 | CASNo_Ref = | ChEBI = 135465 | ChEMBL = 1788384 | ChemSpiderID = 8107 | ChemSpiderID_Ref = | DrugBank = DB08928 | EINECS = 204-361-7 | KEGG_Ref = | KEGG = D07356 | PubChem = 8414 | UNII_Ref = | UNII = QNT09A162Y | SMILES = CC(=O)NC1=C(O)C=CC(=C1)[As]1SCC(CO)S1 | SMILES1 = O=C(Nc2cc([As]1SCC(S1)CO)ccc2O)C | StdInChI = 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) | StdInChI_Ref = | 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) | StdInChIKey = MRUDSZSRLQAPOG-UHFFFAOYSA-N | StdInChIKey_Ref = | InChIKey = MRUDSZSRLQAPOG-UHFFFAOYAP}} |Section2={{Chembox Properties | C=11 | H=14 | As=1 | N=1 | O=3 | S=2}} |Section6={{Chembox Pharmacology | ATCCode_prefix = P01 | ATCCode_suffix = AR01 | ATC_Supplemental = | AdminRoutes = Oral | Metabolism = 89 % Hepatic}} Arsthinol (INN) is an organoarsenic compound with the formula . A antiprotozoal agent, it was first reported in 1949. It arises by the reaction of acetarsol with 2,3-dimercaptopropanol (British anti-Lewisite) and has been demonstrated to be effective against amoebiasis and yaws. It was marketed a few years later by Endo Products (Balarsen, Tablets, 0.1 g).

Among trivalent organoarsenicals, arsthinol was considered very well tolerated. Recently, it was studied for its anticancer activity.

Properties

For Arsthinol the hydrogen bond donor count of 3, a hydrogen bond acceptor count of 5, a complexity of 308, and contains no isotope atoms. It is chiral but marketed as the racemate.

References

References

  1. (1975). "Voies et cinétiques d'excrétion de l'arsenic chez le Cobaye après injection de divers médicaments organo-arséniés". [[Ann Pharm Fr]].
  2. (1949). "A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical". [[Am J Trop Med Hyg]].
  3. (1953). "New and nonofficial remedies; arsthinol". [[J Am Med Assoc]].
  4. (1956). "Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen)". [[JAMA (journal).
  5. (2006). "(2-Phenyl-[1, 3, 2] dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity". [[J Organomet Chem]].
  6. (2013). "The antitumor effects of an arsthinol-cyclodextrin complex in an heterotopic mouse model of glioma". [[Eur J Pharm Biopharm]].
  7. PubChem. "Arsthinol".

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antiprotozoal-agentsacetanilideshydroxymethyl-compoundsphenolsorganoarsenic-dithiolatesarsenic-heterocyclesarsenic(iii)-compoundssulfur-heterocyclesheterocyclic-compounds-with-1-ring