Arsthinol

Arsthinol

Structural formula of arsthinol
Names
Preferred IUPAC name N-{2-Hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide
Identifiers
CAS Number	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
PubChem CID	8414
UNII	QNT09A162Y  Y
CompTox Dashboard (EPA)	DTXSID40861753
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) 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
SMILES CC(=O)NC1=C(O)C=CC(=C1)[As]1SCC(CO)S1 O=C(Nc2cc([As]1SCC(S1)CO)ccc2O)C
Properties
Chemical formula	C11H14AsNO3S2
Molar mass	347.28 g·mol−1
Pharmacology
ATC code	P01AR01 ( WHO ) QP51AD01 ( WHO )
Routes of administration	Oral
Pharmacokinetics:
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  YN ?) Infobox references

Arsthinol (INN) is an organoarsenic compound with the formula 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) ^[2] 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). ^[3]

Among trivalent organoarsenicals, arsthinol was considered very well tolerated. ^[4] Recently, it was studied for its anticancer activity. ^{[5] [6]}

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. ^[7]

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, 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.
7. PubChem. "Arsthinol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-10-17.