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Identification
NameAminosalicylic Acid
Accession NumberDB00233  (APRD00749, EXPT00693)
TypeSmall Molecule
GroupsApproved
Description

An antitubercular agent often administered in association with isoniazid. The sodium salt of the drug is better tolerated than the free acid. [PubChem]

Structure
Thumb
Synonyms
2-HYDROXY-4-aminobenzoic acid
4-aminosalicylate
4-aminosalicylic acid
Aminosalicylic acid
p-aminosalicylic acid
para-amino salicylic acid
para-aminosalicylic acid
PAS
Paser
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nemasol Sodium Tab 500mgtablet500 mgoralIcn Canada Ltd.1966-12-312005-04-26Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pasergranule, delayed release4 g/1oralJacobus Pharmaceutical Company, Inc.1995-02-152016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
PamisylParke-Davis
RexipasBristol-Myers Squibb
RezipasBristol-Myers Squibb
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Aminosalicylate Sodium
Thumb
  • InChI Key: FVVDKUPCWXUVNP-UHFFFAOYSA-M
  • Monoisotopic Mass: 175.024537738
  • Average Mass: 175.1172
DBSALT000354
Categories
UNII5B2658E0N2
CAS number65-49-6
WeightAverage: 153.1354
Monoisotopic: 153.042593095
Chemical FormulaC7H7NO3
InChI KeyInChIKey=WUBBRNOQWQTFEX-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
IUPAC Name
4-amino-2-hydroxybenzoic acid
SMILES
NC1=CC(O)=C(C=C1)C(O)=O
Taxonomy
DescriptionThis compound 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
Substituents
  • Aminosalicylic acid
  • Salicylic acid
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Substituted aniline
  • Benzoyl
  • Aminophenol
  • Phenol
  • Aniline
  • Primary aromatic amine
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of tuberculosis
PharmacodynamicsAminosalicylic 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 Mycobacterium tuberculosis (prevents the multiplying of bacteria without destroying them). It also inhibits the onset of bacterial resistance to streptomycin and isoniazid.
Mechanism of actionThere 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding50-60%
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=4 gm/kg (orally in mice); LD50=3650 mg/kg (orally in rabbits)
Affected organisms
  • Mycobacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9356
Blood Brain Barrier-0.7101
Caco-2 permeable-0.852
P-glycoprotein substrateNon-substrate0.8405
P-glycoprotein inhibitor INon-inhibitor0.9777
P-glycoprotein inhibitor IINon-inhibitor0.9905
Renal organic cation transporterNon-inhibitor0.9337
CYP450 2C9 substrateNon-substrate0.8174
CYP450 2D6 substrateNon-substrate0.8358
CYP450 3A4 substrateNon-substrate0.7782
CYP450 1A2 substrateNon-inhibitor0.8645
CYP450 2C9 inhibitorNon-inhibitor0.8281
CYP450 2D6 inhibitorNon-inhibitor0.9627
CYP450 2C19 inhibitorInhibitor0.5778
CYP450 3A4 inhibitorNon-inhibitor0.7324
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9157
Ames testNon AMES toxic0.9388
CarcinogenicityNon-carcinogens0.8045
BiodegradationReady biodegradable0.6246
Rat acute toxicity1.5761 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9689
hERG inhibition (predictor II)Non-inhibitor0.9676
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Century pharmaceuticals inc
  • Hexcel chemical products
  • Panray corp sub ormont drug and chemical co inc
  • Lannett co inc
  • Consolidated midland corp
  • Jacobus pharmaceutical co
  • Bristol myers squibb co
Packagers
Dosage forms
FormRouteStrength
Tabletoral500 mg
Granule, delayed releaseoral4 g/1
Prices
Unit descriptionCostUnit
Paser granules 4 gm packet3.59USD packet
Aminosalicylic acid powder2.4USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point150.5 dec °CPhysProp
water solubility1690 mg/L (at 23 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.89SANGSTER (1994)
pKa2.05 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility11.8 mg/mLALOGPS
logP0.62ALOGPS
logP0.83ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m3·mol-1ChemAxon
Polarizability14.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.18 KB)
SpectraNot Available
References
Synthesis Reference

Thomas M. Parkinson, Joseph P. Brown, Robert E. Wingard, Jr., “Pharmaceutical preparations containing a polymeric agent for releasing 5-aminosalicylic acid or its salts into the gastrointestinal tract.” U.S. Patent US4298595, issued January, 1975.

US4298595
General ReferencesNot Available
External Links
ATC CodesJ04AA01
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
AbciximabAminosalicylic Acid may increase the anticoagulant activities of Abciximab.
AcenocoumarolAminosalicylic Acid may increase the anticoagulant activities of Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Acetazolamide.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Aminosalicylic Acid.
AlteplaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Alteplase.
Ammonium chlorideThe serum concentration of Aminosalicylic Acid can be increased when it is combined with Ammonium chloride.
AnistreplaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Anistreplase.
Citric AcidAminosalicylic Acid may increase the anticoagulant activities of Citric Acid.
DalteparinAminosalicylic Acid may increase the anticoagulant activities of Dalteparin.
DesmopressinThe risk or severity of adverse effects can be increased when Desmopressin is combined with Aminosalicylic Acid.
DexketoprofenThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Dexketoprofen.
DiclofenamideThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Diclofenamide.
DicoumarolAminosalicylic Acid may increase the anticoagulant activities of Dicoumarol.
Edetic AcidAminosalicylic Acid may increase the anticoagulant activities of Edetic Acid.
EnoxaparinAminosalicylic Acid may increase the anticoagulant activities of Enoxaparin.
EthoxzolamideThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Ethoxzolamide.
Ethyl biscoumacetateAminosalicylic Acid may increase the anticoagulant activities of Ethyl biscoumacetate.
FludrocortisoneThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Fludrocortisone.
Fondaparinux sodiumAminosalicylic Acid may increase the anticoagulant activities of Fondaparinux sodium.
Ginkgo bilobaGinkgo biloba may increase the anticoagulant activities of Aminosalicylic Acid.
HeparinAminosalicylic Acid may increase the anticoagulant activities of Heparin.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Aminosalicylic Acid.
Insulin HumanAminosalicylic Acid may increase the hypoglycemic activities of Insulin Regular.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Aminosalicylic Acid.
PerindoprilAminosalicylic Acid may decrease the antihypertensive activities of Perindopril.
PhenindioneAminosalicylic Acid may increase the anticoagulant activities of Phenindione.
PhenprocoumonAminosalicylic Acid may increase the anticoagulant activities of Phenprocoumon.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Aminosalicylic Acid.
ProbenecidThe therapeutic efficacy of Probenecid can be decreased when used in combination with Aminosalicylic Acid.
ReteplaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Reteplase.
RidogrelThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Ridogrel.
StreptokinaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Streptokinase.
SulodexideAminosalicylic Acid may increase the anticoagulant activities of Sulodexide.
TenecteplaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Tenecteplase.
TorasemideAminosalicylic Acid may decrease the diuretic activities of Torasemide.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Aminosalicylic Acid.
UrokinaseThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Urokinase.
Valproic AcidThe serum concentration of Valproic Acid can be increased when it is combined with Aminosalicylic Acid.
WarfarinAminosalicylic Acid may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Scaffold protein binding
Specific Function:
Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or other cellular stresses. Acts as part of the canonical IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B on serine residues. These modifications...
Gene Name:
CHUK
Uniprot ID:
O15111
Molecular Weight:
84638.88 Da
References
  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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Iron ion binding
Specific Function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular Weight:
77982.595 Da
References
  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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
unknown
General Function:
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:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular Weight:
15988.525 Da
References
  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 ]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
Actions
unknown
General Function:
Coenzyme transport and metabolism
Specific Function:
Not Available
Gene Name:
folK
Uniprot ID:
P64143
Molecular Weight:
20732.0 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
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:
MPO
Uniprot ID:
P05164
Molecular Weight:
83867.71 Da
References
  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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08