Arsthinol

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
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) 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