Drug/Small Molecule:
aminosalicylic acid

2D structure

Overview

Generic Names: 4-ASA; 4-aminosalicylic acid; APAS; Amino-PAS; Aminosalicylate Sodium; P-Aminosalicylic Acid; PAS; PASK; Para-Amino Salicylic Acid; Para-aminosalicylic acid
Trade Names: Aminopar; Aminox; Apacil; Deapasil; Entepas; Ferrosan; Gabbropas; Hellipidyl; Kyselina P-Aminosalicylova; Neopasalate; Osacyl; PAS-C; Pamacyl; Pamisyl; Para-Pas; Paramycin; Parasal; Parasalicil; Parasalindon; Pasa; Pasalon; Pasara; Pascorbic; Pasdium; Pasem; Paser; Pasmed; Pasnodia; Pasolac; Propasa; Rezipas; Sanipirol-4; Sanipriol-4
PharmGKB Accession Id: PA448382

Description

An antitubercular agent often administered in association with isoniazid. The sodium salt of the drug is better tolerated than the free acid. PubChem (source: Drug Bank)

Indication

For the treatment of tuberculosis (source: Drug Bank)

ATC Therapeutic Category

  • J04AA:Aminosalicylic acid and derivatives

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against <i>Mycobacterium tuberculosis</i>. Firstly, aminosalicylic acid inhibits folic acid synthesis (without potentiation with antifolic compounds). The binding of para-aminobenzoic acid to pteridine synthetase acts as the first step in folic acid synthesis. Aminosalicylic acid binds pteridine synthetase with greater affinity than para-aminobenzoic acid, effectively inhibiting the synthesis of folic acid. As bacteria are unable to use external sources of folic acid, cell growth and multiplication slows. Secondly, aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by <i>M. tuberculosis</i>. (source: Drug Bank)

Pharmacology

Aminosalicylic acid is an anti-mycobacterial agent used with other anti-tuberculosis drugs (most often isoniazid) for the treatment of all forms of active tuberculosis due to susceptible strains of tubercle bacilli. The two major considerations in the clinical pharmacology of aminosalicylic acid are the prompt production of a toxic inactive metabolite under acid conditions and the short serum half life of one hour for the free drug. Aminosalicylic acid is bacteriostatic against <i>Mycobacterium tuberculosis</i> (prevents the multiplying of bacteria without destroying them). It also inhibits the onset of bacterial resistance to streptomycin and isoniazid. (source: Drug Bank)

Food Interactions

Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. (source: Drug Bank)

Protein Binding

50-60% (source: Drug Bank)

Toxicity

LD<sub>50</sub>=4 gm/kg (orally in mice); LD<sub>50</sub>=3650 mg/kg (orally in rabbits) (source: Drug Bank)

Isomeric SMILES Code:

NC1=CC(O)=C(C=C1)C(O)=O (source: Drug Bank)

A list of non-curated publications that mention this drug along with other genes is available.

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
azathioprine Uncurated Annotation The 5-ASA derivative increases the toxicity of thiopurine (source: Drug Bank)
mercaptopurine Uncurated Annotation The 5-ASA derivative increases the toxicity of thiopurine (source: Drug Bank)
thioguanine Uncurated Annotation The 5-ASA derivative increases the toxicity of thiopurine (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00233
KEGG Compound ID:
C02518
KEGG Drug ID:
D00162
PubChem Compound ID:
4649
PubChem Substance ID:
5528

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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