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Acetarsol

Summary

Acetarsol (or acetarsone[1]) is an anti-infective drug.[2]

Acetarsol
Kekulé, skeletal formula of acetarsol
Names
Preferred IUPAC name
(3-Acetamido-4-hydroxyphenyl)arsonic acid
Other names
Acetarsone
Identifiers
  • 97-44-9 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:135135
ChEMBL
  • ChEMBL1330792 checkY
ChemSpider
  • 1908 checkY
DrugBank
  • DB13268
ECHA InfoCard 100.002.349 Edit this at Wikidata
EC Number
  • 202-582-3
KEGG
  • D07110 checkY
MeSH Acetarsol
  • 1985
UNII
  • 806529YU1N checkY
UN number 3465
  • DTXSID9045847 Edit this at Wikidata
  • 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) checkY
    Key: ODFJOVXVLFUVNQ-UHFFFAOYSA-N checkY
  • InChI=1/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)
    Key: ODFJOVXVLFUVNQ-UHFFFAOYAX
  • CC(=O)Nc1cc(ccc1O)[As](O)(O)=O
  • CC(=O)NC1=CC(=CC=C1O)[As](O)(O)=O
Properties
C8H10AsNO5
Molar mass 275.0903 g mol−1
Pharmacology
A07AX02 (WHO) G01AB01 (WHO), P01CD02 (WHO), P51AD05 (WHO)
Hazards
GHS labelling:
GHS06: Toxic GHS09: Environmental hazard
Danger
H301, H331, H410
P261, P273, P301+P310, P311, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

It was first discovered in 1921 at Pasteur Institute by Ernest Fourneau,[3] and sold under the brand name Stovarsol.[4][5] It has been given in the form of suppositories.[6]

Acetarsol can be used to make arsthinol.[citation needed]

It has been cancelled and withdrawn from the market since August 12th, 1997.[3]

Medical uses edit

Acetarsol has been used for the treatment of diseases such as syphilis, amoebiasis, yaws, trypanosomiasisiasis and malaria. Acetarsol was used for the treatment of Trichomonas Vaginalis and Candida Albicans. In the oral form, acetarsol can be used for the treatment of intestinal amoebiasis. As a suppository, acetarsol was researched to be used for the treatment of proctitis.[3]

Mechanism of Action edit

Although the mechanism of action is not fully known, acetarsol may bind to protein-containing sulfhydryl groups located in the parasite, which then creates lethal As-S bonds, which then kills the parasite. [3]

Chemistry and pharmacokinetics edit

Acetarsol has the molecular formula N-acetyl-4-hydroxy-m-arsinillic acid, and it is a pentavalent arsenical compound with antiprotozoal and anthelmintic properties. The arsenic found in acetarsol is excreted mainly in urine. The level of arsenic after acetarsol administration reaches close to the toxic range in urine.[3] Some reports indicate a remission of arsenic which can be physiologically dangerous. [3]

Toxicity edit

Some reports indicate that acetarsol can produce effects in the eyes such as optic neuritis and optic atrophy.[7]

References edit

  1. ^ "FDA Substance Registration System: Acetarsol". Archived from the original on 8 January 2021. Retrieved 6 May 2021.
  2. ^ Chen MY, Smith NA, Fox EF, Bingham JS, Barlow D (April 1999). "Acetarsol pessaries in the treatment of metronidazole resistant Trichomonas vaginalis". Int J STD AIDS. 10 (4): 277–80. doi:10.1258/0956462991913943. PMID 12035784. S2CID 27353282.
  3. ^ a b c d e f PubChem. "Acetarsol". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-03-31.
  4. ^ "Éric Fouassier, Ces poisons qui guérissent, oct. 1996, p. 5" (PDF). Archived from the original (PDF) on 2011-10-05. Retrieved 2010-04-01.
  5. ^ Traité de chimie organique, sous la direction de Victor Grignard, Paul Baud, vol. 22, Masson, 1959, p. 1127-1130.
  6. ^ Gionchetti P, Rizzello F, Morselli C, Campieri M (October 2004). "Review article: problematic proctitis and distal colitis". Aliment. Pharmacol. Ther. 20 (Suppl 4): 93–6. doi:10.1111/j.1365-2036.2004.02049.x. PMID 15352902. S2CID 72699260.
  7. ^ PubChem. "Acetarsol". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-01-16.