Acetarsol

Identification

Name
Acetarsol
Accession Number
DB13268
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Acetarsol, with the molecular formula N-acetyl-4-hydroxy-m-arsanilic acid, is a pentavalent arsenical compound with antiprotozoal and antihelmintic properties.[8] It was first discovered in 1921 by Ernest Fourneau at the Pasteur Institute. It was developed by Neolab Inc, and approved by Health Canada as an antifungal on December 31, 1964. It has been canceled and withdrawn from the market since August 12, 1997.[L113]

Structure
Thumb
Synonyms
Not Available
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Neo VagexAcetarsol (100 mg) + Benzalkonium chloride (2 mg) + Clioquinol (50 mg)TabletVaginalNeolab Inc1964-12-311997-08-12Canada
Categories
UNII
806529YU1N
CAS number
97-44-9
Weight
Average: 275.0903
Monoisotopic: 274.977493852
Chemical Formula
C8H10AsNO5
InChI Key
ODFJOVXVLFUVNQ-UHFFFAOYSA-N
InChI
InChI=1S/C8H10AsNO5/c1-5(11)10-7-4-6(9(13,14)15)2-3-8(7)12/h2-4,12H,1H3,(H,10,11)(H2,13,14,15)
IUPAC Name
(3-acetamido-4-hydroxyphenyl)arsonic acid
SMILES
CC(=O)NC1=CC(=CC=C1O)[As](O)(O)=O

Pharmacology

Indication

Acetarsol has been used for the treatment of different diseases such as syphilis, amoebiasis, yaws, trypanosomiasis, and malaria.[9] Acetarsol was used commonly for the treatment of vaginitis due to Trichomonas vaginalis and Candida albicans.[1, 2] When orally administered, acetarsol can be used for the treatment of intestinal amoebiasis and in the form of suppositories it has been researched for the treatment of proctitis.[10]

Protozoan infections are parasitic diseases characterized to be caused by organisms classified in the kingdom Protozoa which is formed by a great diversity of organisms.[11]

Associated Conditions
Pharmacodynamics

Some reports indicate a certain infection remission with the use of acetarsol but this reports also demonstrate the absorption of systemic arsenic which can be physiologically dangerous.[3]

Mechanism of action

The mechanism of action of acetarsol is not well known but it is thought to bind to protein-containing sulfhydryl groups located in the infective microorganism and to form a lethal As-S bond. The formation of this bond impairs the protein to function and it eventually kills the microorganism.[8]

Absorption

The absorption seems to be very minimal but there are reports of allergic reactions after vaginal administration of acetarsol.[1]

Volume of distribution

This pharmacokinetic property was not addressed.

Protein binding

This pharmacokinetic property was not addressed.

Metabolism

This pharmacokinetic property was not addressed.

Route of elimination

The arsenic found in acetarsol is excreted mainly in the urine.[5] The level of arsenic after acetarsol administration almost reaches the toxic range in urine.[4]

Half life

This pharmacokinetic property was not addressed.

Clearance

This pharmacokinetic property was not addressed.

Toxicity

The administration of inorganic arsenic is highly carcinogenic and thus acetarsol if thought to be dangerous when absorbed.[4] Some reports indicate that acetarsol can produce effects in the eyes such as optic neuritis and optic atrophy.[6]

Affected organisms
  • Humans and other mammals
  • Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Acetarsol which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AlprazolamAlprazolam may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AmilorideAmiloride may increase the excretion rate of Acetarsol which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAcetarsol may decrease the excretion rate of Amitriptyline which could result in a higher serum level.
AmlodipineAmlodipine may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AmoxicillinAmoxicillin may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AmphetamineAmphetamine may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AmpicillinAmpicillin may decrease the excretion rate of Acetarsol which could result in a higher serum level.
AuranofinAuranofin may decrease the excretion rate of Acetarsol which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. PECK BJ: Exfoliative dermatitis after acetarsol vaginal pessaries. Br Med J. 1954 Oct 9;2(4892):850-1. [PubMed:13199327]
  2. WHITE A: Acute systemic reaction to acetarsol. Br Med J. 1956 Dec 29;2(5008):1528-9. [PubMed:13374373]
  3. Lawrance IC: Novel topical therapies for distal colitis. World J Gastrointest Pharmacol Ther. 2010 Oct 6;1(5):87-93. doi: 10.4292/wjgpt.v1.i5.87. [PubMed:21577301]
  4. Kiely CJ, Clark A, Bhattacharyya J, Moran GW, Lee JC, Parkes M: Acetarsol Suppositories: Effective Treatment for Refractory Proctitis in a Cohort of Patients with Inflammatory Bowel Disease. Dig Dis Sci. 2018 Apr;63(4):1011-1015. doi: 10.1007/s10620-017-4890-6. Epub 2018 Feb 19. [PubMed:29457211]
  5. Nath R. (2000). Health and disease role of micronutrients and trace elements. New Apcon. [ISBN:81-7648-125-4]
  6. Morton W. and Schuman J. (1993). Toxicology of the eye (4th ed.). Charles C Thomas. [ISBN:0-398-05860-1]
  7. Health Canada [Link]
  8. National Cancer Institute [Link]
  9. NIH [Link]
  10. NHS [Link]
  11. NIH [Link]
External Links
ChemSpider
1908
ChEBI
135135
ChEMBL
CHEMBL1330792
Wikipedia
Acetarsol
ATC Codes
P01CD02 — AcetarsolG01AB01 — AcetarsolA07AX02 — Acetarsol
MSDS
Download (79.7 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)225-227 ºC'MSDS'
water solubilitySlightly soluble Schnitzer J. and Hawking F. 1963. Experimental chemotherapy.
Predicted Properties
PropertyValueSource
Water Solubility2.8 mg/mLALOGPS
logP-0.15ALOGPS
logP-0.031ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.89 m3·mol-1ChemAxon
Polarizability21.45 Å3ChemAxon
Number of Rings1ChemAxon
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 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 / Pentaorganoarsanes / Acetamides / Secondary carboxylic acid amides / Oxygen-containing organoarsenic compounds / Organic metalloid salts / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Acetanilide / N-acetylarylamine / N-arylamide / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Pentaorganoarsane / Acetamide / Carboxamide group / Secondary carboxylic acid amide / Carboxylic acid derivative
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:38 / Updated on August 02, 2018 06:50