Arsthinol

Identification

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Name
Arsthinol
Accession Number
DB08928
Type
Small Molecule
Groups
Experimental
Description

Arsthinol (INN) is an antiprotozoal agent that was first synthesized by Ernst A.H. Friedheim in 1949 via the complexing of acetarsol with 2,3-dimercaptopropanol. It has since been demonstrated that the agent possesses activity against amoebas and yaws. Considered well tolerated when compared to other related trivalent organoarsenicals, arsthinol has even undergone recent studies as a potential anticancer agent.

Structure
Thumb
Synonyms
  • Arsthinenol
International/Other Brands
Balarsen (Endo Products)
Categories
UNII
QNT09A162Y
CAS number
119-96-0
Weight
Average: 347.285
Monoisotopic: 346.963106116
Chemical Formula
C11H14AsNO3S2
InChI Key
MRUDSZSRLQAPOG-UHFFFAOYSA-N
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)
IUPAC Name
N-{2-hydroxy-5-[4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl]phenyl}acetamide
SMILES
CC(=O)NC1=CC(=CC=C1O)[As]1SCC(CO)S1

Pharmacology

Indication

Antiprotozoal agent effective against amoebiasis and yaws.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

89% Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral,mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.

Affected organisms
  • Protozoa
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Cristau B, Chabas E, Placidi M: [Pathways and kinetics of arsenic excretion in the guinea pig after injections of various organo-arsenic drugs]. Ann Pharm Fr. 1975 Nov;33(11):577-89. [PubMed:1231604]
External Links
KEGG Drug
D07356
PubChem Compound
8414
PubChem Substance
175427160
ChemSpider
8107
ChEBI
135465
ChEMBL
CHEMBL1788384
Wikipedia
Arsthinol
ATC Codes
P01AR01 — Arsthinol
MSDS
Download (607 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP1.11ChemAxon
pKa (Strongest Acidic)8.52ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.33 m3·mol-1ChemAxon
Polarizability30.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Acetanilides
Alternative Parents
N-acetylarylamines / 1-hydroxy-2-unsubstituted benzenoids / Acetamides / Trivalent organic arsenic compounds / Secondary carboxylic acid amides / Oxygen-containing organoarsenic compounds / Organoheterocyclic compounds / Organoarsenic sulfides / Organic metalloid salts / Primary alcohols
show 4 more
Substituents
Acetanilide / N-acetylarylamine / N-arylamide / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Acetamide / Carboxamide group / Secondary carboxylic acid amide / Trivalent organic arsenic compound / Carboxylic acid derivative
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 08, 2013 14:49 / Updated on June 04, 2019 07:04