4-Aminosalicylic acid

4-Aminosalicylic acid
Clinical data
Trade names	Paser, Granupas, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Aminosalicylic acid;
Routes of; administration	By mouth
ATC code	J04AA01 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	50–60%
Metabolism	liver
Excretion	kidney
Identifiers
	IUPAC name 4-Amino-2-hydroxybenzoic acid;
CAS Number	65-49-6 ;
PubChem CID	4649;
DrugBank	DB00233 ;
ChemSpider	4488 ;
UNII	5B2658E0N2;
KEGG	D00162 ;
ChEBI	CHEBI:27565 ;
ChEMBL	ChEMBL1169 ;
NIAID ChemDB	020064;
PDB ligand	BHA (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID2022591 ;
ECHA InfoCard	100.000.557
Chemical and physical data
Formula	C7H7NO3
Molar mass	153.137 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	150.5 °C (302.9 °F)
	SMILES OC(=O)c1ccc(N)cc1O;
	InChI InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11) ; Key:WUBBRNOQWQTFEX-UHFFFAOYSA-N ;
	(verify)

4-Aminosalicylic acid, also known as para-aminosalicylic acid (PAS) and sold under the brand name Paser among others, is an antibiotic primarily used to treat tuberculosis.^[2] Specifically it is used to treat active drug resistant tuberculosis together with other antituberculosis medications.^[3] It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease.^[3] It is typically taken by mouth.^[3]

Common side effects include nausea, abdominal pain, and diarrhea.^[3] Other side effects may include liver inflammation and allergic reactions.^[3] It is not recommended in people with end stage kidney disease.^[3] While there does not appear to be harm with use during pregnancy it has not been well studied in this population.^[3] 4-Aminosalicylic acid is believed to work by blocking the ability of bacteria to make folic acid.^[3]

4-Aminosalicylic acid was first made in 1902, and came into medical use in 1943.^[4] It is on the World Health Organization's List of Essential Medicines.^[5]

^ Cite error: The named reference Granupas EPAR was invoked but never defined (see the help page).
^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 140. hdl:10665/44053. ISBN 9789241547659.
^ ^a ^b ^c ^d ^e ^f ^g ^h "Aminosalicylic Acid". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ Donald PR, Diacon AH (September 2015). "Para-aminosalicylic acid: the return of an old friend". The Lancet. Infectious Diseases. 15 (9): 1091–1099. doi:10.1016/s1473-3099(15)00263-7. PMID 26277036.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[Granupas_EPAR-1] Cite error: The named reference Granupas EPAR was invoked but never defined (see the help page).

[WHO2008-2] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 140. hdl:10665/44053. ISBN 9789241547659.

[AHFS2016-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Aminosalicylic Acid". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[Lancet2015-4] Donald PR, Diacon AH (September 2015). "Para-aminosalicylic acid: the return of an old friend". The Lancet. Infectious Diseases. 15 (9): 1091–1099. doi:10.1016/s1473-3099(15)00263-7. PMID 26277036.

[WHO23rd-5] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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