Acetarsol

Identification

Summary

Acetarsol is an anti infective used to treat a wide variety of infections in the body.

Generic Name

Acetarsol

DrugBank Accession Number

DB13268

Background

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 It has been canceled and withdrawn from the market since August 12, 1997.⁷

Type

Small Molecule

Groups

Approved, Withdrawn

Structure

Similar Structures

Weight: Average: 275.0903
Monoisotopic: 274.977493852
Chemical Formula: C₈H₁₀AsNO₅

Synonyms

Acetarsol

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

Pharmacology

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Associated Conditions

Contraindications & Blackbox Warnings

Contraindications

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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.

Adverse Effects

Adverseeffects

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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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: Not Available

Products

Products2

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dosage, form, labeller, route of administration, and marketing period.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Neo Vagex	Acetarsol (100 mg) + Benzalkonium chloride (2 mg) + Clioquinol (50 mg)	Tablet	Vaginal	Neolab Inc	1964-12-31	1997-08-12

Categories

ATC Codes

G01AB01 — Acetarsol

P01CD02 — Acetarsol

A07AX02 — Acetarsol

Drug Categories

Chemical TaxonomyProvided by Classyfire

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 / Carbonyl compounds
show 1 more
Substituents: 1-hydroxy-2-unsubstituted benzenoid / Acetamide / Acetanilide / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / N-acetylarylamine / N-arylamide
show 13 more
Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: Not Available

Affected organisms

Humans and other mammals
Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica

Chemical Identifiers

UNII: 806529YU1N
CAS number: 97-44-9
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

References

General References

PECK BJ: Exfoliative dermatitis after acetarsol vaginal pessaries. Br Med J. 1954 Oct 9;2(4892):850-1. [Article]
WHITE A: Acute systemic reaction to acetarsol. Br Med J. 1956 Dec 29;2(5008):1528-9. [Article]
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. [Article]
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. [Article]
Nath R. (2000). Health and disease role of micronutrients and trace elements. New Apcon. [ISBN:81-7648-125-4]
Morton W. and Schuman J. (1993). Toxicology of the eye (4th ed.). Charles C Thomas. [ISBN:0-398-05860-1]
Health Canada [Link]
National Cancer Institute [Link]
NIH [Link]
NHS [Link]
NIH [Link]

External Links

ChemSpider: 1908
BindingDB: 50240028
ChEBI: 135135
ChEMBL: CHEMBL1330792
Wikipedia: Acetarsol

MSDS

Download (79.7 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Vaginal

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	225-227 ºC	'MSDS'
water solubility	Slightly soluble	Schnitzer J. and Hawking F. 1963. Experimental chemotherapy.

Predicted Properties

Property	Value	Source
Water Solubility	2.8 mg/mL	ALOGPS
logP	-0.15	ALOGPS
logP	-0.031	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.89 m³·mol^-1	ChemAxon
Polarizability	21.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Drug created on June 23, 2017 20:38 / Updated on April 24, 2021 16:10