Acetarsol

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Acetarsol
Kekulé, skeletal formula of acetarsol
Names
Preferred IUPAC name
(3-Acetamido-4-hydroxyphenyl)arsonic acid
Other names
Acetarsone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.349 Edit this at Wikidata
EC Number
  • 202-582-3
KEGG
MeSH Acetarsol
UNII
UN number 3465
  • 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 ?)

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

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.

It has been cancelled and withdrawn from the market since August 12th, 1997.[3]

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.[3]

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. [3]

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.[3] Some reports indicate a remission of arsenic which can be physiologically dangerous. [3]

Toxicity

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

References

  1. ^ "FDA Substance Registration System: Acetarsol". 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.
  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.