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Acetarsol
View on Wikipedia
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| Names | |
|---|---|
| Preferred IUPAC name
(3-Acetamido-4-hydroxyphenyl)arsonic acid | |
| Other names
Acetarsone
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.002.349 |
| EC Number |
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| KEGG | |
| MeSH | Acetarsol |
PubChem CID
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| UNII | |
| UN number | 3465 |
CompTox Dashboard (EPA)
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| Properties | |
| C8H10AsNO5 | |
| Molar mass | 275.0903 g mol−1 |
| Pharmacology | |
| A07AX02 (WHO) G01AB01 (WHO), P01CD02 (WHO), P51AD05 (WHO) | |
| Hazards | |
| GHS labelling: | |
 
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| 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).
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Acetarsol (or acetarsone,[1] also known as spirocid[2]) is an anti-infective drug.[3] It was first discovered in 1921 at Pasteur Institute by Ernest Fourneau,[4] and sold under the brand name Stovarsol.[5][6] It was available in oral form and also as a suppository.[7] It has been cancelled and withdrawn from the market since August 12, 1997.[4]
Acetarsol can be used to make arsthinol.[citation needed]
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.[4]
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. [4]
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.[4] Some reports indicate a remission of arsenic which can be physiologically dangerous. [4]
Toxicity
[edit]Some reports indicate that acetarsol can produce effects in the eyes such as optic neuritis and optic atrophy.[8]
References
[edit]- ^ "FDA Substance Registration System: Acetarsol". Archived from the original on 8 January 2021. Retrieved 6 May 2021.
- ^ Rosenbaum HA (1932). "Stovarsol in the Treatment of Syphilis in Infants and in Children". American Journal of Diseases of Children. 44 (1): 25–30.
- ^ 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.
- ^ a b c d e f PubChem. "Acetarsol". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-03-31.
- ^ "Éric Fouassier, Ces poisons qui guérissent, oct. 1996, p. 5" (PDF). Archived from the original (PDF) on 2011-10-05. Retrieved 2010-04-01.
- ^ Traité de chimie organique, sous la direction de Victor Grignard, Paul Baud, vol. 22, Masson, 1959, p. 1127-1130.
- ^ 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.
- ^ PubChem. "Acetarsol". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-01-16.