Acetarsol

Structural formula
General
Surname	Acetarsol
other names	N -acetyl-4-hydroxy- m -arsanilic acid; 3-acetamido-4-hydroxyphenylarsonic acid; Acetarsone; Acetphenarsine;
Molecular formula	C 8 H 10 AsNO 5
Brief description	white solid
External identifiers / databases
ECHA InfoCard	100.002.349
PubChem	1985
Wikidata	Q584079
Drug information
ATC code	A07 AX02 , G01 AB01 , P01 CD02
properties
Molar mass	275.09 g mol −1
Physical state	firmly
Melting point	225-227 ° C
solubility	practically insoluble in cold water and ethanol; soluble in dilute bases;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301-331-410
	P: 261-273-301 + 310 + 330-304-340-312-403 + 233-501
Toxicological data	4 mg kg −1 ( LD 50 , mouse , oral ) ; 155 mg kg −1 ( LD Lo , woman , intra vaginal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acetarsol is a chemical compound from the group of organic arsenic compounds .

history

Acetarsol was already used by Paul Ehrlich in 1911 as an intermediate for the production of arsphenamine- analogue. Ernest Fourneau arranged the production under the name Stovarsol by Poulenc Freres . It turned out to be a potent remedy for syphilis.

Extraction and presentation

Acetarsol can be obtained from 4-chloroaniline . By reaction thereof with sodium nitrite , Natriumorthoarsenit it is converted to 4-chloro-3-nitro-phenylarsonic acid, which with sodium thiosulfate or sodium hydroxide reacts to form 3-amino-4-hydroxy-phenylarsonic acid, which in turn with acetic anhydride is converted to Acetarsol.

properties

Acetarsol is a white odorless powder with a slightly sour taste that is practically insoluble in cold water and ethanol. The dimethylamine and sodium salts are also white odorless powders, but they are soluble in water.

use

Acetarsol is used to treat amoebiasis and trichomoniasis . The dimethylamine and sodium salts are also used.

safety instructions

Hallucinations and disturbed perceptions may occur when the connection is established. If swallowed, stomach irritation, nausea, vomiting and diarrhea can occur.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet Acetarsone, ≥99% from Sigma-Aldrich , accessed on December 26, 2015 ( PDF ).
↑ ^a ^b ^c ^d F. v. Bruchhausen, Siegfried Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 22 ( limited preview in Google Book search).
↑ Walter Sneader: Drug Discovery A History . John Wiley & Sons, 2005, ISBN 978-0-471-89979-2 , pp. 55 ( limited preview in Google Book search).
↑ ^a ^b P. H. List, L. Hörhammer: Chemicals and Drugs (Am - Ch) . Springer-Verlag, 2013, ISBN 978-3-642-80562-2 , p. 252 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet Acetarsone, ≥99% from Sigma-Aldrich , accessed on December 26, 2015 ( PDF ).

[F.v._Bruchhausen,_Siegfried_Ebel,_A.W._Frahm,_E._Hackenthal-2] F. v. Bruchhausen, Siegfried Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 22 ( limited preview in Google Book search).

[Walter_Sneader-3] Walter Sneader: Drug Discovery A History . John Wiley & Sons, 2005, ISBN 978-0-471-89979-2 , pp. 55 ( limited preview in Google Book search).

[P._H._List,_L._Hörhammer-4] P. H. List, L. Hörhammer: Chemicals and Drugs (Am - Ch) . Springer-Verlag, 2013, ISBN 978-3-642-80562-2 , p. 252 ( limited preview in Google Book search).