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Arsthinol

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, arsthinol was considered as very well tolerated.[4] Recently, it was studied for its anticancer activity.[5][6]

Arsthinol
Names
Preferred IUPAC name
N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide
Identifiers
  • 119-96-0 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:135465
ChEMBL
  • ChEMBL1788384
ChemSpider
  • 8107 Y
DrugBank
  • DB08928
ECHA InfoCard 100.003.965
EC Number
  • 204-361-7
KEGG
  • D07356 Y
  • 8414
UNII
  • QNT09A162Y Y
  • 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) Y
    Key: MRUDSZSRLQAPOG-UHFFFAOYSA-N Y
  • 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
  • CC(=O)NC1=C(O)C=CC(=C1)[As]1SCC(CO)S1
  • O=C(Nc2cc([As]1SCC(S1)CO)ccc2O)C
Properties
C11H14AsNO3S2
Molar mass 347.28 g·mol−1
Pharmacology
P01AR01 (WHO) QP51AD01 (WHO)
Oral
Pharmacokinetics:
89 % Hepatic[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

References edit

  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, 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. doi:10.4269/ajtmh.1949.s1-29.185. PMID 18116845.
  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 (5): 360–363. doi:10.1001/jama.1956.02960400018005. PMID 13278204.
  5. ^ 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 (5): 1081–1084. doi:10.1016/j.jorganchem.2005.11.007.
  6. ^ 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" (PDF). Eur J Pharm Biopharm. 85 (3): 560–568. doi:10.1016/j.ejpb.2013.06.021. PMID 23831266.

arsthinol, antiprotozoal, agent, synthesized, first, time, 1949, ernst, friedheim, complexation, acetarsol, with, dimercaptopropanol, british, anti, lewisite, been, demonstrated, effective, against, amoebiasis, yaws, marketed, years, later, endo, products, bal. 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 arsthinol was considered as very well tolerated 4 Recently it was studied for its anticancer activity 5 6 Arsthinol NamesPreferred IUPAC name N 2 Hydroxy 5 4 hydroxymethyl 1 3 2 dithiarsolan 2 yl phenyl acetamideIdentifiersCAS Number 119 96 0 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 135465ChEMBL ChEMBL1788384ChemSpider 8107 YDrugBank DB08928ECHA InfoCard 100 003 965EC Number 204 361 7KEGG D07356 YPubChem CID 8414UNII QNT09A162Y YInChI 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 YKey MRUDSZSRLQAPOG UHFFFAOYSA N YInChI 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 UHFFFAOYAPSMILES CC O NC1 C O C CC C1 As 1SCC CO S1O C Nc2cc As 1SCC S1 CO ccc2O CPropertiesChemical formula C 11H 14As N O 3S 2Molar mass 347 28 g mol 1PharmacologyATC code P01AR01 WHO QP51AD01 WHO Routes ofadministration OralPharmacokinetics Metabolism 89 Hepatic 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesReferences edit Cristau B Chabas ME Placidi M 1975 Voies et cinetiques d excretion de l arsenic chez le Cobaye apres injection de divers medicaments organo arsenies 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 doi 10 4269 ajtmh 1949 s1 29 185 PMID 18116845 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 5 360 363 doi 10 1001 jama 1956 02960400018005 PMID 13278204 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 5 1081 1084 doi 10 1016 j jorganchem 2005 11 007 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 PDF Eur J Pharm Biopharm 85 3 560 568 doi 10 1016 j ejpb 2013 06 021 PMID 23831266 nbsp This antiinfective drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Arsthinol amp oldid 1104699953, wikipedia, wiki, book, books, library,

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