para-aminosalicylic acid   Click here for help

GtoPdb Ligand ID: 13652

Synonyms: 4-aminosalicylic acid | Granupas® | p-aminosalicylic acid | Paser® | Rezipas®
Approved drug PDB Ligand
para-aminosalicylic acid is an approved drug (FDA, EMA (2014))
Compound class: Synthetic organic
Comment: Para-aminosalicylic acid is a structural analogue of 4-aminobenzoic acid (pABA) with activity against mycobacteria. It was one of the first drugs to be introduced as a treatment for tuberculosis (TB) [2-3].

para-aminosalicylic acid is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 83.55
Molecular weight 153.14
XLogP 0.2
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C1=C(C=C(C(=C1)C(=O)O)O)N
Isomeric SMILES C1=CC(=C(C=C1N)O)C(=O)O
InChI InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
InChI Key WUBBRNOQWQTFEX-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Para-aminosalicylic acid is indicated for the treatment of active TB when first-line therapies cannot be used because of resistance and/or intolerance. It is administered orally and in conjunction with other TB medicines. The World Health Organization's Model List of Essential Medicines includes para-aminosalicylic acid on the complementary list, under the category of antituberculosis medicines.
It has been used off-label in the US, for the treatment of mild to moderate ulcerative colitis in patients intolerant of sulfasalazine and in the treatment of Crohn's disease.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
In Mycobacterium tuberculosis, studies indicate that para-aminosalicylic acid acts as a prodrug that is bioactivated within the folate pathway, leading to disruption of folate synthesis by inhibition of dihydrofolate reductase (DHFR) [1,4].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)