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Acetarsol

Names
Preferred IUPAC name (3-Acetamido-4-hydroxyphenyl)arsonic acid
Other names Acetarsone
Identifiers
CAS Number	97-44-9
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:135135
ChEMBL	ChEMBL1330792
ChemSpider	1908
DrugBank	DB13268
ECHA InfoCard	100.002.349
EC Number	202-582-3
KEGG	D07110
MeSH	Acetarsol
PubChem CID	1985
UNII	806529YU1N
UN number	3465
CompTox Dashboard (EPA)	DTXSID9045847
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)Key: ODFJOVXVLFUVNQ-UHFFFAOYSA-N 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
SMILES CC(=O)Nc1cc(ccc1O)(O)(O)=O CC(=O)NC1=CC(=CC=C1O)(O)(O)=O
Properties
Chemical formula	C8H10AsNO5
Molar mass	275.0903 g mol
Pharmacology
ATC code	A07AX02 (WHO) G01AB01 (WHO), P01CD02 (WHO), P51AD05 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H331, H410
Precautionary statements	P261, P273, P301+P310, P311, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Acetarsol (or acetarsone) is an anti-infective drug.

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

Acetarsol can be used to make arsthinol.

It has been cancelled and withdrawn from the market since August 12th, 1997.

Medical uses

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.

Mechanism of action

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.

Chemistry and pharmacokinetics

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. Some reports indicate a remission of arsenic which can be physiologically dangerous.

Toxicity

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

References

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. ^ 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.

• Antiprotozoal agents
• Acetanilides
• Arsonic acids
• Phenols