Acetarsol
Identification
- Name
- Acetarsol
- Accession Number
- DB13268
- 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 It has been canceled and withdrawn from the market since August 12, 1997.[L113]
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Acetarsol (DB13268)
- Weight
- Average: 275.0903
Monoisotopic: 274.977493852 - Chemical Formula
- C8H10AsNO5
- Synonyms
- Not Available
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
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- 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
- 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
- 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 Canada 
Categories
- ATC Codes
- G01AB01 — Acetarsol
- G01AB — Arsenic compounds
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- P01CD — Arsenic compounds
- P01C — AGENTS AGAINST LEISHMANIASIS AND TRYPANOSOMIASIS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Agents Against Leishmaniasis and Trypanosomiasis
- Alimentary Tract and Metabolism
- Anti-Infective Agents
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Arsenicals
- Drugs that are Mainly Renally Excreted
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Intestinal Antiinfectives
- Organometallic Compounds
- 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 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
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. [PubMed:13199327]
- WHITE A: Acute systemic reaction to acetarsol. Br Med J. 1956 Dec 29;2(5008):1528-9. [PubMed:13374373]
- 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]
- 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]
- 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
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 14:38 / Updated on June 12, 2020 10:53
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