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Home > Encyclopedia > N-Acetyl-4-hydroxy-m-arsanilic acid

N-Acetyl-4-hydroxy-m-arsanilic acid

N-Acetyl-4-hydroxy-m-arsanilic acid structure

N-Acetyl-4-hydroxy-m-arsanilic acid 

structure
  • CAS No:

    97-44-9

  • Formula:

    C8H10AsNO5

  • Chemical Name:

    N-Acetyl-4-hydroxy-m-arsanilic acid

  • Synonyms:

    Arsonic acid,As-[3-(acetylamino)-4-hydroxyphenyl]-;m-Arsanilic acid,N-acetyl-4-hydroxy-;Arsonic acid,[3-(acetylamino)-4-hydroxyphenyl]-;As-[3-(Acetylamino)-4-hydroxyphenyl]arsonic acid;3-Acetamido-4-hydroxybenzenearsonic acid;Acetarsol;Acetarsone;Acetphenarsine;3-Acetylamino-4-hydroxyphenylarsonic acid;3-Acetylamino-4-hydroxyphenyl-1-arsonic acid;N-Acetyl-4-hydroxy-m-arsanilic acid;Amarsan;Amoebal;Arsaphen;Chrlich 594;Devegan;Disparicida;Dynarsan;Ehrlich 594;Fourneau 190;Ginarsol;Goyl;Kharophen;Kubarsol;Limarsol;Malagride;Monargan;Nilacid;Oralcid;Orarsan;Osarsal;Osarsol;Osvarsan;Pallicid;Paroxyl;Spirocid;Spirozid;Stovarsol;Stovarsolan;SVC;Vagisept;Osarsole;190F;F 190;Gynoplix;3-Acetamido-4-hydroxyphenylarsonic acid;Vagoflor;Mexyl;Arsonine;Sanogyl;NSC 13160;NSC 3247

  • Categories:

    Organic Chemistry  >  Arsenicals

Description

Acetarsol is a member of acetamides and an anilide.|Acetarsol, with the molecular formula N-acetyl-4-hydroxy-m-arsanilic acid, is a pentavalent arsenical compound with antiprotozoal and antihelmintic properties. It was first discovered in 1921 by Ernest Fourneau at the Pasteur Institute. It was developed by Neolab Inc, and approved by Health Canada as an antifungal on December 31, 1964. It has been canceled and withdrawn from the market since August 12, 1997.|Acetarsol is a pentavalent arsenical compound with antiprotozoal and antihelmintic properties. Although its mechanism of action is not fully known, acetarsone may bind to protein-containing sulfhydryl groups located in the parasite, thereby forming lethal As-S bonds. This may prevent their functioning and eventually kill the parasite.

N-Acetyl-4-hydroxy-m-arsanilic acid Basic Attributes

275.09

275.09

202-582-3

806529YU1N

757386|13160|3247

DTXSID9045847

C61621

A - Alimentary tract and metabolism|G - Genito urinary system and sex hormones|P - Antiparasitic products, insecticides and repellents

2931900090

Characteristics

107

-1.01540

1.0325 g/cm3 @ Temp: 15 °C

220-221 °C

72.17°C

H2O: Slightly soluble

Oral-Mouse LD50: 4 mg/kg

Flammable; decomposes by heating to release extremely toxic nitrogen oxides and arsenic fumes

151.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

III

6.1(b)

UN 3465 6.1/PG 2

3

23/25-50/53

20/21-28-45-60-61

CF8400000

T,N

Warehouse ventilated, low temperature and dry

P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, P501

H301+H331

|Danger|H301+H331 (100%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]|P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

most toxic

The administration of inorganic arsenic is highly carcinogenic and thus acetarsol if thought to be dangerous when absorbed. Some reports indicate that acetarsol can produce effects in the eyes such as optic neuritis and optic atrophy.

This pharmacokinetic property was not addressed.

Drug Information

Acetarsol has been used for the treatment of different diseases such as syphilis, amoebiasis, yaws, trypanosomiasis, and malaria. Acetarsol was used commonly for the treatment of vaginitis due to _Trichomonas vaginalis_ and _Candida albicans_. When orally administered, acetarsol can be used for the treatment of intestinal amoebiasis and in the form of suppositories it has been researched for the treatment of proctitis. Protozoan infections are parasitic diseases characterized to be caused by organisms classified in the kingdom Protozoa which is formed by a great diversity of organisms.

Some reports indicate a certain infection remission with the use of acetarsol but this reports also demonstrate the absorption of systemic arsenic which can be physiologically dangerous.

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

The absorption seems to be very minimal but there are reports of allergic reactions after vaginal administration of acetarsol.|The arsenic found in acetarsol is excreted mainly in the urine. The level of arsenic after acetarsol administration almost reaches the toxic range in urine.|This pharmacokinetic property was not addressed.

This pharmacokinetic property was not addressed.

This pharmacokinetic property was not addressed.

The mechanism of action of acetarsol is not well known but it is thought to bind to protein-containing sulfhydryl groups located in the infective microorganism and to form a lethal As-S bond. The formation of this bond impairs the protein to function and it eventually kills the microorganism.

acetarsol

N-Acetyl-4-hydroxy-m-arsanilic acid Use and Manufacturing

antiprotozoal; diethylamine salt as antiphilitic

Computed Properties

Molecular Weight:275.09
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:274.977492
Monoisotopic Mass:274.977492
Topological Polar Surface Area:107
Heavy Atom Count:15
Complexity:289
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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    CAS No.: 97-44-9
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