U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C7H6NO3.Na.2H2O
Molecular Weight 211.1478
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOSALICYLATE SODIUM

SMILES

O.O.[Na+].NC1=CC=C(C([O-])=O)C(O)=C1

InChI

InChIKey=GMUQJDAYXZXBOT-UHFFFAOYSA-M
InChI=1S/C7H7NO3.Na.2H2O/c8-4-1-2-5(7(10)11)6(9)3-4;;;/h1-3,9H,8H2,(H,10,11);;2*1H2/q;+1;;/p-1

HIDE SMILES / InChI

Description

4-AMINOSALICYLIC ACID (Paser) is an anti-tuberculosis drug used to treat tuberculosis in combination with other active agents. 4-AMINOSALICYLIC ACID (Paser) is most commonly used in patients with Multi-drug Resistant TB (MDR-TB) or when isoniazid and rifampin use is not possible due to a combination of resistance and/or intolerance. There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against Mycobacterium tuberculosis. 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 the 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 slow. Secondly, the aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by M. tuberculosis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PASER
Primary
PASER
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
82.69 mg/L
8 g 1 times / day multiple, oral
AMINOSALICYLIC ACID plasma
Homo sapiens
53.63 mg/L
4 g 2 times / day multiple, oral
AMINOSALICYLIC ACID plasma
Homo sapiens
16.36 mg/L
8 g 1 times / day multiple, oral
4-ACETAMIDOSALICYLIC ACID plasma
Homo sapiens
14.59 mg/L
4 g 2 times / day multiple, oral
4-ACETAMIDOSALICYLIC ACID plasma
Homo sapiens
20 μg/mL
4 g single, oral
AMINOSALICYLIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
690.35 mg × h/L
8 g 1 times / day multiple, oral
AMINOSALICYLIC ACID plasma
Homo sapiens
414.07 mg × h/L
4 g 2 times / day multiple, oral
AMINOSALICYLIC ACID plasma
Homo sapiens
142.49 mg × h/L
8 g 1 times / day multiple, oral
4-ACETAMIDOSALICYLIC ACID plasma
Homo sapiens
145.02 mg × h/L
4 g 2 times / day multiple, oral
4-ACETAMIDOSALICYLIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.62 h
4 g single, oral
AMINOSALICYLIC ACID plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
4 g single, oral
AMINOSALICYLIC ACID plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
The adult dosage of four grams (one packet) three times per day or correspondingly smaller doses in children.
Route of Administration: Oral
In Vitro Use Guide
5.0 ug/mL MIC against mycobacterium tuberculosis.