arsthinol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 457817818

| ImageFile = Arsthinol.svg

| ImageFile_Ref = {{Chemboximage|correct|??}}

| 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 = {{Cascite|correct|CAS}}

| ChEBI = 135465

| ChEMBL = 1788384

| ChemSpiderID = 8107

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| DrugBank = DB08928

| EINECS = 204-361-7

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07356

| PubChem = 8414

| UNII_Ref = {{fdacite|correct|FDA}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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 = {{ATCvet|P51|AD01}}

| AdminRoutes = Oral

| Metabolism = 89 % Hepatic{{cite journal | last1 = Cristau | first1 = B | last2 = Chabas | first2 = ME | last3 = Placidi | first3 = M | year = 1975 | title = Voies et cinétiques d'excrétion de l'arsenic chez le Cobaye après injection de divers médicaments organo-arséniés | journal = Ann Pharm Fr | volume = 33 | pages = 577–89 }}}}

}}

Arsthinol (INN) is an organoarsenic compound with the formula {{chem2|HOCH2CHCH2S2AsC6H3(OH)NHCOCH3}}. A antiprotozoal agent, it was first reported in 1949. It arises by the reaction of acetarsol with 2,3-dimercaptopropanol (British anti-Lewisite){{cite journal | last1 = Friedheim | first1 = Ernst AH | year = 1949 | title = A Five Day Peroral Treatment of Yaws with STB, a New Trivalent Arsenical | journal = Am J Trop Med Hyg | volume = s1-29 | issue = 2 | pages = 185–188 | doi = 10.4269/ajtmh.1949.s1-29.185 | pmid = 18116845 }} 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).{{cite journal | last1 = Anonyme | year = 1953 | title = New and nonofficial remedies; arsthinol | journal = J Am Med Assoc | volume = 152 | page = 531 }}

Among trivalent organoarsenicals, arsthinol was considered very well tolerated.{{cite journal | last1 = Brown | first1 = CH | last2 = Gebhart | first2 = WF | last3 = Reich | first3 = A | year = 1956 | title = Intestinal amebiasis: incidence, symptoms, and treatment with arsthinol (Balarsen) | journal = JAMA | volume = 160 | issue = 5| pages = 360–363 | doi=10.1001/jama.1956.02960400018005| pmid = 13278204 }} Recently, it was studied for its anticancer activity.{{cite journal | last1 = Gibaud | first1 = S | last2 = Alfonsi | first2 = R | last3 = Mutzenhardt | first3 = P |display-authors=et al | year = 2006 | title = (2-Phenyl-[1, 3, 2] dithiarsolan-4-yl)-methanol derivatives show in vitro antileukemic activity | journal = J Organomet Chem | volume = 691 | issue = 5| pages = 1081–1084 | doi=10.1016/j.jorganchem.2005.11.007}}{{cite journal | last1 = Becherirat | first1 = S. | last2 = Lanhers | first2 = M.-C. | last3 = Socha | first3 = M. | last4 = Yemloul | first4 = M. | last5 = Astier | first5 = A. | last6 = Loboda | first6 = C. | last7 = Aniceto | first7 = N. | last8 = Gibaud | first8 = S. | year = 2013 | title = The antitumor effects of an arsthinol-cyclodextrin complex in an heterotopic mouse model of glioma | url = https://hal.archives-ouvertes.fr/hal-01169157/file/Eur%20J%20Pharm%20Biopharm%202013%20Becherirat.pdf| journal = Eur J Pharm Biopharm | volume = 85| issue = 3| pages = 560–568| doi = 10.1016/j.ejpb.2013.06.021 | pmid = 23831266 }}