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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:31 UTC
Secondary Accession Numbers
  • HMDB14378
Metabolite Identification
Common NameAminosalicylic Acid
DescriptionAminosalicylic Acid is only found in individuals that have used or taken this drug. It is an antitubercular agent often administered in association with isoniazid. The sodium salt of the drug is better tolerated than the free acid. [PubChem]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 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 M. tuberculosis.
2-HYDROXY-4-aminobenzoIC ACIDChEBI
p-Aminosalicylic acidChEBI
Para-amino salicylic acidChEBI
4-Aminosalicylic acidKegg
Para-amino salicylateGenerator
Aminosalicylate sodiumHMDB
Para-aminosalicylic acidHMDB
4 Aminosalicylic acidHMDB
p-Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid, monosodium salt, dihydrateHMDB
Acid, aminosalicylicHMDB
Alumino 4 aminosalicylic acidHMDB
p Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acidHMDB
p Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, aluminum (2:1) saltHMDB
Para aminosalicylic acidHMDB
Alumino-4-aminosalicylic acidHMDB
p-Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, calcium (2:1) saltHMDB
Aminosalicylic acidChEBI
Chemical FormulaC7H7NO3
Average Molecular Weight153.1354
Monoisotopic Molecular Weight153.042593095
IUPAC Name4-amino-2-hydroxybenzoic acid
Traditional Nameaminosalicylic acid
CAS Registry Number65-49-6
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminosalicylic acids
Alternative Parents
  • 4-aminosalicylic acid
  • Aminosalicylic acid
  • Salicylic acid
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Aniline or substituted anilines
  • M-aminophenol
  • Aminophenol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.8 g/LNot Available
LogP1.6Not Available
Predicted Properties
Water Solubility11.8 g/LALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.29 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2900000000-f96d42a6d732787e860eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-2190000000-77c54a0901141e0c25ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-9edb9b6028f854f76708Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-e893f1439cefbeef271aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-5900000000-09273d1390d26a8def2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-9200000000-e029b385a8c32e95b6b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00ku-9000000000-58cccd83d40f8fade4dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-06dr-2900200000-832b5b02326d8b11bac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-a497dd61e37afd19159fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-771daa6ebfd132e803a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9400000000-a2c0beef5eb5e0f96f27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-1900000000-f74138cc6d19303f955cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-82ef8276edc66459ee1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9500000000-347557516c4726a8670dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00233 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00233 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00233
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4488
KEGG Compound IDC02518
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminosalicylic_Acid
METLIN IDNot Available
PubChem Compound4649
ChEBI ID27565
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. JUHASZ P, GALAMBOS G: [A simple paper-indicator method for the demonstration of paraaminosalicylic acid (PAS) in urine]. Tuberkulozis. 1961 Jun;14:186-7. [PubMed:13790963 ]
  2. Iyawoo K: Tuberculosis in Malaysia: problems and prospect of treatment and control. Tuberculosis (Edinb). 2004;84(1-2):4-7. [PubMed:14670340 ]
  3. Authors unspecified: Controlled trial of short-course regimens of chemotherapy in the ambulatory treatment of spinal tuberculosis. Results at three years of a study in Korea. Twelfth report of the Medical Research Council Working Party on Tuberculosis of the Spine. J Bone Joint Surg Br. 1993 Mar;75(2):240-8. [PubMed:8444944 ]
  4. Tiitinen H, Mattila MJ: Modification of the serum isoniazid levels by different preparations of paraaminosalicylic acid. Arzneimittelforschung. 1968 May;18(5):623-5. [PubMed:5755895 ]
  5. ARTIS RD, JOHNSON PK, FREE AH: A simplified test for the detection of paraaminosalicylic acid and acetylsalicylic acid metabolites in urine. Am Rev Respir Dis. 1961 Sep;84:435-9. [PubMed:13684569 ]
  6. Ojo OA, Onifade A, Akande EO, Bannerman RH: The pattern of female genital tuberculosis in Ibadan. Isr J Med Sci. 1971 Feb;7(2):280-7. [PubMed:5560983 ]
  7. Shah A, Panjabi C, Maurya V, Khanna P: Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient. Saudi Med J. 2004 Oct;25(10):1468-70. [PubMed:15494824 ]
  8. NAITO M: [Combined therapy of massive doses of isoniazid, pyrazinamide, and sulfisoxazole for patients with pulmonary tuberculosis resistant to streptomycin, paraaminosalicylic acid, and isoniazid]. Kyoto Daigaku Kekkaku Kenkyusho Kiyo. 1961 Mar;9:136-41. [PubMed:14478036 ]
  9. KENDIG EL Jr, HUDGENS RO: The effect of rubeola on tuberculosis under antimicrobial therapy. II. Tuberculous meningitis treated with isoniazid, streptomycin and paraaminosalicylic acid. Pediatrics. 1959 Oct;24:619-22. [PubMed:14408481 ]
  10. Joshi JV, Joshi UM, Sankolli GM, Gupta K, Rao AP, Hazari K, Sheth UK, Saxena BN: A study of interaction of a low-dose combination oral contraceptive with anti-tubercular drugs. Contraception. 1980 Jun;21(6):617-29. [PubMed:7428368 ]
  11. MITROIU O, POPA M, NEGREANU W, BILCU M, POPPER M, KAUFMANN S, NICULESCU V, VANCOV Z: [The differential diagnosis of jaundices appearing during treatment with paraaminosalicylic acid (PAS) by means of serum aldolase determination]. Stud Cercet Inframicrobiol. 1960;11:125-31. [PubMed:14423031 ]
  12. MILLER FF, GREEN RA: Loeffler's syndrome due to paraaminosalicylic acid. Dis Chest. 1962 Jul;42:100-3. [PubMed:14473996 ]
  13. Miroshnichenko II, Sokolova GB, Mokhireva LV: [Clinical pharmacokinetics of para-aminosalicylic acid tablets]. Antibiot Khimioter. 2009;54(1-2):20-4. [PubMed:19499713 ]
  14. SCHMITTOVA M, ENGELBERTH O, SRAMKOVA J: [Effect of aminopyrine, paraaminobenzoic acid and paraaminosalicylic acid on experimental carditis in mice]. Cas Lek Cesk. 1959 Oct 30;98:1365-9. [PubMed:14443158 ]
  15. Wong SC, Ali MA: Hemoglobin E diseases: hematological, analytical, and biosynthetic studies in homozygotes and double heterozygotes for alpha-thalassemia. Am J Hematol. 1982 Aug;13(1):15-21. [PubMed:7137163 ]
  16. Costello HD, Caras GJ, Snider DE Jr: Drug resistance among previously treated tuberculosis patients, a brief report. Am Rev Respir Dis. 1980 Feb;121(2):313-6. [PubMed:6767427 ]
  18. Vachova-Fribova M, Elis J: [Effect of theophylline and isoprenaline on N-acetylation activity in the rat liver]. Farmakol Toksikol. 1978 Mar-Apr;41(2):191-3. [PubMed:658363 ]
  19. Bader G: [Electron microscopic studies on pathological liver regeneration under the influence of thioacetamide, paraaminosalicylic acid and barbiturate]. Acta Hepatosplenol. 1969 May-Jun;16(3):160-73. [PubMed:5799611 ]


General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
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Molecular weight:
  1. von Ritter C, Grisham MB, Granger DN: Sulfasalazine metabolites and dapsone attenuate formyl-methionyl-leucyl-phenylalanine-induced mucosal injury in rat ileum. Gastroenterology. 1989 Mar;96(3):811-6. [PubMed:2563347 ]
  2. Gorgulu S, Yagci G, Kaymakcioglu N, Ozkara M, Kurt B, Ozcan A, Kaya O, Sadir S, Tufan T: Hyperbaric oxygen enhances the efficiency of 5-aminosalicylic acid in acetic acid-induced colitis in rats. Dig Dis Sci. 2006 Mar;51(3):480-7. [PubMed:16614956 ]
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Nielsen OH, Bukhave K, Elmgreen J, Ahnfelt-Ronne I: Inhibition of 5-lipoxygenase pathway of arachidonic acid metabolism in human neutrophils by sulfasalazine and 5-aminosalicylic acid. Dig Dis Sci. 1987 Jun;32(6):577-82. [PubMed:2882965 ]
  2. Allgayer H, Eisenburg J, Paumgartner G: Soybean lipoxygenase inhibition: studies with the sulphasalazine metabolites N-acetylaminosalicylic acid, 5-aminosalicylic acid and sulphapyridine. Eur J Clin Pharmacol. 1984;26(4):449-51. [PubMed:6428914 ]
  3. Sircar JC, Schwender CF, Carethers ME: Inhibition of soybean lipoxygenase by sulfasalazine and 5-aminosalicylic acid: a possible mode of action in ulcerative colitis. Biochem Pharmacol. 1983 Jan 1;32(1):170-2. [PubMed:6131674 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
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  1. Mifflin RC, Saada JI, Di Mari JF, Valentich JD, Adegboyega PA, Powell DW: Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8. [PubMed:14742690 ]
  2. Generini S, Fiori G, Matucci Cerinic M: Therapy of spondylarthropathy in inflammatory bowel disease. Clin Exp Rheumatol. 2002 Nov-Dec;20(6 Suppl 28):S88-94. [PubMed:12463455 ]
  3. Distrutti E, Sediari L, Mencarelli A, Renga B, Orlandi S, Russo G, Caliendo G, Santagada V, Cirino G, Wallace JL, Fiorucci S: 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3yl)-phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol Exp Ther. 2006 Oct;319(1):447-58. Epub 2006 Jul 19. [PubMed:16855178 ]
  4. Cipolla G, Crema F, Sacco S, Moro E, de Ponti F, Frigo G: Nonsteroidal anti-inflammatory drugs and inflammatory bowel disease: current perspectives. Pharmacol Res. 2002 Jul;46(1):1-6. [PubMed:12208114 ]
  5. Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [PubMed:9256165 ]
General function:
Involved in protein kinase activity
Specific function:
Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. As part of the non-canonical pathway of NF-kappa-B activation, the MAP3K14-activated CHUK/IKKA homodimer phosphorylates NFKB2/p100 associated with RelB, inducing its proteolytic processing to NFKB2/p52 and the formation of NF-kappa-B RelB-p52 complexes. Also phosphorylates NCOA3. Phosphorylates 'Ser-10' of histone H3 at NF- kappa-B-regulated promoters during inflammatory responses triggered by cytokines
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  1. Bantel H, Berg C, Vieth M, Stolte M, Kruis W, Schulze-Osthoff K: Mesalazine inhibits activation of transcription factor NF-kappaB in inflamed mucosa of patients with ulcerative colitis. Am J Gastroenterol. 2000 Dec;95(12):3452-7. [PubMed:11151876 ]
  2. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [PubMed:12950415 ]
  3. Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [PubMed:11054378 ]