Acetarsol: Difference between revisions

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			{{cs1 config\|name-list-style=vanc}}
	{{Chembox		{{Chembox
	\| Verifiedfields = changed		\| Verifiedfields = changed
			\| Watchedfields = changed
	\| verifiedrevid = 477238724		\| verifiedrevid = 477238724
	\| ImageFile = Acetarsol.svg		\| ImageFile = Acetarsol.svg
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	\| 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_Ref = {{cascite\|~~changed~~\|??}}
	\| CASNo = 97-44-9		\| CASNo = 97-44-9
			\| ChEBI = 135135
	\| ChEMBL_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 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}}
			\|Section7={{Chembox Hazards
	\| EUClass = {{Hazchem T}} {{Hazchem N}}
	\| ~~RPhrases~~ = {{~~R23/25~~}}, {{~~R50/53~~}}		\| GHSPictograms = {{GHS skull and crossbones}} {{GHS environment}}
		⚫	\| GHSSignalWord = Danger
	\| SPhrases = {{S20/21}}, {{S28}}, {{S45}}, {{S60}}, {{S61}}
		⚫	\| HPhrases = {{H-phrases\|301\|331\|410}}
		⚫	\| PPhrases = {{P-phrases\|261\|273\|301+310\|311\|501}}
	}}		}}
	}}		}}

	'''Acetarsol''' is an anti-infective.<ref name="pmid12035784">{{cite journal \|~~author~~=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 \|~~year~~=1999 ~~\|month=April~~ \|pmid=12035784 \|doi= 10.1258/0956462991913943\|url=http://ijsa.rsmjournals.com/cgi/pmidlookup?view=long&pmid=12035784}}</ref>		'''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 ], and sold under the brand name '''Stovarsol''' ~~(''fourneau'' is the French word for stove)~~. <ref></ref> <ref>''Traité de chimie organique'', sous la direction de Victor Grignard, Paul Baud, vol. 22, Masson, 1959, p. 1127-1130.</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 given in ].<ref name="pmid15352902">{{cite journal \|author=Gionchetti P, Rizzello F, Morselli C, Campieri M \|title=Review article: problematic proctitis and distal colitis \|journal=Aliment. Pharmacol. Ther. \|volume=20 Suppl 4 \|issue= \|pages=93–6 \|year=2004 \|month=October \|pmid=15352902 \|doi=10.1111/j.1365-2036.2004.02049.x \|url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0269-2813&date=2004&volume=20&issue=&spage=93}}</ref>

			It has been cancelled and withdrawn from the market since August 12th, 1997.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

			== Medical uses ==
⚫	{{Reflist}}
			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 ==
	{{Gastrointestinal-drug-stub}}
			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" />
	{{Antiinfective-drug-stub}}

	{{Genito-urinary-drug-stub}}
			== 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}}		{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}
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	]		]
	]		]

	]
	]
	]
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Latest revision as of 07:38, 20 June 2024

Acetarsol
Names
Kekulé, skeletal formula of acetarsol
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

Chemical compound

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

"FDA Substance Registration System: Acetarsol". Archived from the original on 8 January 2021. Retrieved 6 May 2021.
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.
^ 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.

v t e Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (+atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone Hydrocortisone Prednisone Betamethasone Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
WHO-EM Withdrawn from market Clinical trials: Phase III Never to phase III

Antiparasitics – antiprotozoal agents – Chromalveolata antiparasitics (P01)

Alveo-
late

Apicom-
plexa

Conoidasida/
(Coccidiostats)

Cryptosporidiosis	thiazolides (nitazoxanide)
Isosporiasis	trimethoprim/sulfamethoxazole
Toxoplasmosis	pyrimethamine sulfadiazine clindamycin atovaquone

Individual
agents

4-Methanolquinolines

Other

lumefantrine
- + artemether

halofantrine

Antifolates

DHFR inhibitors

biguanides
- chlorproguanil
- proguanil

Sulfonamides

Co-formulation

sulfadoxine/pyrimethamine (SP)

Sesquiterpene
lactones

Other

Combi-
nations

Fixed-dose (co-formulated) ACTs	artemether/lumefantrine arterolane/piperaquine artesunate/amodiaquine (ASAQ) artesunate/mefloquine (ASMQ) artesunate/pyronaridine piperaquine/dihydroartemisinin
Other combinations (not co-formulated)	artesunate/mefloquine artesunate/SP quinine/clindamycin quinine/doxycycline quinine/tetracycline

Babesiosis

clindamycin

Cilio-
phora

Balantidiasis: tetracycline

Stramen-
opile

Blastocystosis: metronidazole

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Categories: