4-aminosalicylic acid

Structural formula
General
Surname	4-aminosalicylic acid
other names	PAS; 4-amino-2-hydroxybenzoic acid;
Molecular formula	C 7 H 7 NO 3
External identifiers / databases
EC number	200-613-5
ECHA InfoCard	100,000,557
PubChem	4649
DrugBank	DB00233
Wikidata	Q229924
Drug information
ATC code	J04 AA01 ; J04 AA02 ;
Drug class	Antibiotic , antituberculotic
properties
Molar mass	153.14 g · mol -1
Physical state	firmly
Melting point	150.5 ° C
pK s value	2.05
solubility	heavy in water (1.69 g l −1 at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-280-302 + 352-305 + 351 + 338
Toxicological data	3898 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-aminosalicylic acid ( para -aminosalicylic acid , PAS, trade name: PAS-Fatol N (D), manufacturer: Riemser , GRANUPAS (D), manufacturer: Lucane Pharma) is an antibiotic for the treatment of tuberculosis .

presentation

It is represented by carboxylation of 3-aminophenol .

properties

4-Aminosalicylic acid crystallizes in the monoclinic crystal system in the space group P 2 ₁ / c (space group no. 14) with the lattice parameters a = 728 pm , b = 382 pm, c = 2533 pm and β = 103 °. In the unit cell contains four formula units . Template: room group / 14

use

PAS is less effective than other antibiotics used against tuberculosis ( isoniazid , rifampicin , ethambutol , pyrazinamide or streptomycin ). It is no longer used on its own, but it plays a role in the combination of drugs for the treatment of multi- drug- resistant tuberculosis. It is a prodrug in Mycobacterium tuberculosis because, like the actual substrate p-aminobenzoic acid , it is incorporated in the bacterium by dihydropteroate synthase in the folate metabolism , which leads to an inhibition of dihydrofolate reductase .

PAS was also used at times for the treatment of chronic inflammatory bowel diseases ( ulcerative colitis and Crohn's disease ).

Individual evidence

↑ ^a ^b ^c ^d Entry on 4-aminosalicylic acid in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b Entry on 4-aminosalicylic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ SC Mitchell, RH Waring: Aminophenols. In: Ullmann's Encyclopedia of Industrial Chemistry. 2002 Wiley-VCH, doi : 10.1002 / 14356007.a02_099 .
^ F. Bertinotti, G. Giacomello, AM Liquori: Crystal and Molecular Structure of p-Amino-Salicylic Acid. In: Acta Cryst. 1954; 7, p. 808; doi: 10.1107 / S0365110X54002502 .
↑ J. Zheng, EJ Rubin a. a .: para-Aminosalicylic Acid Is a Prodrug Targeting Dihydrofolate Reductase in Mycobacterium tuberculosis. In: The Journal of biological chemistry . Volume 288, Number 32, August 2013, pp. 23447-23456, doi: 10.1074 / jbc.M113.475798 . PMID 23779105 .
^ F. Daniel, P. Seksik, W. Cacheux, R. Jian, P. Marteau: Tolerance of 4-aminosalicylic acid enemas in patients with inflammatory bowel disease and 5-aminosalicylic-induced acute pancreatitis . In: Inflamm Bowel Dis . tape 10 , no. 3 , 2004, p. 258-260 , doi : 10.1097 / 00054725-200405000-00013 , PMID 15290921 .

[GESTIS-1] Entry on 4-aminosalicylic acid in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[ChemIDplus-2] Entry on 4-aminosalicylic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Mitchell_Waring-3] SC Mitchell, RH Waring: Aminophenols. In: Ullmann's Encyclopedia of Industrial Chemistry. 2002 Wiley-VCH, doi : 10.1002 / 14356007.a02_099 .

[Bertinotti-4] F. Bertinotti, G. Giacomello, AM Liquori: Crystal and Molecular Structure of p-Amino-Salicylic Acid. In: Acta Cryst. 1954; 7, p. 808; doi: 10.1107 / S0365110X54002502 .

[5] J. Zheng, EJ Rubin a. a .: para-Aminosalicylic Acid Is a Prodrug Targeting Dihydrofolate Reductase in Mycobacterium tuberculosis. In: The Journal of biological chemistry . Volume 288, Number 32, August 2013, pp. 23447-23456, doi: 10.1074 / jbc.M113.475798 . PMID 23779105 .

[6] F. Daniel, P. Seksik, W. Cacheux, R. Jian, P. Marteau: Tolerance of 4-aminosalicylic acid enemas in patients with inflammatory bowel disease and 5-aminosalicylic-induced acute pancreatitis . In: Inflamm Bowel Dis . tape 10 , no. 3 , 2004, p. 258-260 , doi : 10.1097 / 00054725-200405000-00013 , PMID 15290921 .