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Revision as of 19:50, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456778200 of page Acetarsol for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').  Latest revision as of 07:38, 20 June 2024 edit ObserveOwl (talk | contribs)Extended confirmed users, Rollbackers5,586 editsm Reverted 2 edits by 2409:4050:E1F:494A:0:0:4EC8:C011 (talk) to last revision by MarbletanTags: Twinkle Undo 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 399304535 | verifiedrevid = 477238724
| ImageFile = Acetarsol.svg | ImageFile = Acetarsol.svg
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 244 | ImageSize = 244
| ImageName = Kekulé, skeletal formula of acetarsol | ImageName = Kekulé, skeletal formula of acetarsol
| PIN = (3-Acetamido-4-hydroxyphenyl)arsonic acid
| PIN = Acetarsone{{Citation needed|date = June 2011}}
| OtherNames = Acetarsone
| SystematicName = (3-Acetamido-4-hydroxyphenyl)arsonic acid<ref>{{Cite web|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1985|title = acetarsol - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>
⚫ |Section1={{Chembox Identifiers
| OtherNames = 3-Acetamido-4-hydroxyphenylarsonic acid{{Citation needed|date = June 2011}}
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | Section1 = {{Chembox Identifiers
| CASNo = 97-44-9
⚫ | CASNo_Ref = {{cascite|correct|??}}
| ChEBI = 135135
| CASNo = <!-- blanked - oldvalue: 97-44-9 -->
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1330792 --> | ChEMBL = 1330792
| PubChem = 1985 | DrugBank = DB13268
| PubChem = 1985
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
| ChemSpiderID = 1908 | ChemSpiderID = 1908
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 806529YU1N | UNII = 806529YU1N
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 202-582-3 | EINECS = 202-582-3
| UNNumber = 3465 | UNNumber = 3465
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07110 | KEGG = D07110
| MeSHName = Acetarsol | MeSHName = Acetarsol
⚫ | SMILES = CC(=O)Nc1cc(ccc1O)(O)(O)=O
⚫ | ATCCode_prefix = A07
⚫ | SMILES1 = CC(=O)NC1=CC(=CC=C1O)(O)(O)=O
⚫ | ATCCode_suffix = AX02
⚫ | StdInChI = 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)
⚫ | ATC_Supplemental = {{ATC|G01|AB01}}, {{ATC|P01|CD02}}, {{ATC|P51|AD05}}
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | SMILES = CC(=O)Nc1cc(ccc1O)(O)(O)=O
⚫ | 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)
⚫ | SMILES1 = CC(=O)NC1=CC(=CC=C1O)(O)(O)=O
⚫ | StdInChIKey = ODFJOVXVLFUVNQ-UHFFFAOYSA-N
⚫ | StdInChI = 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)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChIKey = ODFJOVXVLFUVNQ-UHFFFAOYAX}}
⚫ | 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)
⚫ |Section2={{Chembox Properties
⚫ | StdInChIKey = ODFJOVXVLFUVNQ-UHFFFAOYSA-N
| C=8|As=1|N=1|H=10|O=5
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | MolarMass = 275.0903 g mol<sup>−1</sup>
⚫ | InChIKey = ODFJOVXVLFUVNQ-UHFFFAOYAX}}
⚫ | Section2 = {{Chembox Properties
| Formula = {{Chem|C|8|AsNH|10|O|5}}
⚫ | MolarMass = 275.0903 g mol<sup>-1</sup>
| ExactMass = 274.977493852 g mol<sup>-1</sup>
}} }}
| Section3 = {{Chembox Hazards |Section6={{Chembox Pharmacology
⚫ | ATCCode_prefix = A07
⚫ | GHSPictograms = {{GHS skull and crossbones}} {{GHS environment}}
⚫ | ATCCode_suffix = AX02
⚫ | GHSSignalWord = Danger
⚫ | ATC_Supplemental = {{ATC|G01|AB01}}, {{ATC|P01|CD02}}, {{ATC|P51|AD05}}
⚫ | HPhrases = {{H-phrases|301|331|410}}
⚫ | PPhrases = {{P-phrases|261|273|301+310|311|501}}
| EUClass = {{Hazchem T}} {{Hazchem N}}
| RPhrases = {{R23/25}}, {{R50/53}}
| SPhrases = {{S20/21}}, {{S28}}, {{S45}}, {{S60}}, {{S61}}
}} }}
|Section7={{Chembox Hazards
⚫ | GHSPictograms = {{GHS skull and crossbones}} {{GHS environment}}
⚫ | GHSSignalWord = Danger
⚫ | HPhrases = {{H-phrases|301|331|410}}
⚫ | PPhrases = {{P-phrases|261|273|301+310|311|501}}
}} }}
}}

'''Acetarsol''' (or '''acetarsone'''<ref>{{cite web|url=https://fdasis.nlm.nih.gov/srs/unii/806529YU1N|title=FDA Substance Registration System: Acetarsol|accessdate=6 May 2021|archive-date=8 January 2021|archive-url=https://web.archive.org/web/20210108134948/https://fdasis.nlm.nih.gov/srs/unii/806529yu1n|url-status=dead}}</ref>) is an anti-] drug.<ref name="pmid12035784">{{cite journal |vauthors=Chen MY, Smith NA, Fox EF, Bingham JS, Barlow D |title=Acetarsol pessaries in the treatment of metronidazole resistant Trichomonas vaginalis |journal=Int J STD AIDS |volume=10 |issue=4 |pages=277–80 |date=April 1999 |pmid=12035784 |doi= 10.1258/0956462991913943|s2cid=27353282 |url=http://ijsa.rsmjournals.com/cgi/pmidlookup?view=long&pmid=12035784}}</ref>

It was first discovered in 1921 at ] by ],<ref name=":0">{{cite web|last=PubChem|title=Acetarsol|url=https://pubchem.ncbi.nlm.nih.gov/compound/1985|access-date=2021-03-31|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref> and sold under the brand name '''Stovarsol'''.<ref>{{cite web |url=http://www.ordre.pharmacien.fr/upload/Syntheses/161.pdf |title=Éric Fouassier, ''Ces poisons qui guérissent'', oct. 1996, p. 5. |access-date=2010-04-01 |archive-date=2011-10-05 |archive-url=https://web.archive.org/web/20111005185843/http://www.ordre.pharmacien.fr/upload/Syntheses/161.pdf |url-status=dead }}</ref><ref>''Traité de chimie organique'', sous la direction de Victor Grignard, Paul Baud, vol. 22, Masson, 1959, p. 1127-1130.</ref> It has been given in the form of ].<ref name="pmid15352902">{{cite journal |vauthors=Gionchetti P, Rizzello F, Morselli C, Campieri M |title=Review article: problematic proctitis and distal colitis |journal=Aliment. Pharmacol. Ther. |volume=20 |pages=93–6 |date=October 2004 |issue=Suppl 4 |pmid=15352902 |doi=10.1111/j.1365-2036.2004.02049.x |s2cid=72699260 |doi-access=free }}</ref>

Acetarsol can be used to make ].{{cn|date=December 2022}}

It has been cancelled and withdrawn from the market since August 12th, 1997.<ref name=":0" />

== Medical uses ==
Acetarsol has been used for the treatment of diseases such as ], ], ], trypanosomiasisiasis and ]. Acetarsol was used for the treatment of ''Trichomonas Vaginalis'' and ''Candida Albicans.'' In the oral form, acetarsol can be used for the treatment of ]. As a suppository, acetarsol was researched to be used for the treatment of proctitis.<ref name=":0" />

== Mechanism of action ==
Although the mechanism of action is not fully known, acetarsol may bind to protein-containing ] groups located in the parasite, which then creates lethal As-S bonds, which then kills the parasite. <ref name=":0" />

== Chemistry and pharmacokinetics ==
Acetarsol has the molecular formula ''N''-acetyl-4-hydroxy-''m''-arsinillic acid, and it is a ] ] compound with ] and ] 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.<ref name=":0" /> Some reports indicate a remission of arsenic which can be physiologically dangerous. <ref name=":0" />

== Toxicity ==
Some reports indicate that acetarsol can produce effects in the eyes such as optic ] and ].<ref>{{cite web|last=PubChem|title=Acetarsol|url=https://pubchem.ncbi.nlm.nih.gov/compound/1985|access-date=2022-01-16|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>

==References==
{{Reflist}}

{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}
{{Agents against leishmaniasis and trypanosomiasis}}

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