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Identification
NameMesalazine
Accession NumberDB00244  (APRD01098)
TypeSmall Molecule
GroupsApproved
Description

An anti-inflammatory agent, structurally related to the salicylates, which is active in inflammatory bowel disease. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed)

Structure
Thumb
Synonyms
3-carboxy-4-hydroxyaniline
5-aminosalicylic acid
5-ASA
Asacol
Asacolitin
Canasa
Claversal
Fisalamine
Iialda
Lixacol
m-Aminosalicylic acid
Mesalamine
Mesalazina
Mesalazine
Mesalazinum
Mesasal
P-Aminosalicylsaeure
Pentasa
Rowasa
Salofalk
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
5-asatablet (enteric-coated)400 mgoralSanis Health Inc2010-11-022012-08-03Canada
Aprisocapsule, extended release375 mg/1oralPhysicians Total Care, Inc.2010-08-18Not applicableUs
Aprisocapsule, extended release375 mg/1oralSalix Pharmaceuticals, Inc.2008-10-31Not applicableUs
Asacoltablet, delayed release400 mg/1oralKAISER FOUNDATION HOSPITALS2012-02-23Not applicableUs
Asacoltablet (enteric-coated)400 mgoralWarner Chilcott Canada Co1993-12-31Not applicableCanada
Asacoltablet, delayed release400 mg/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Asacoltablet400 mg/1oralREMEDYREPACK INC.2011-08-17Not applicableUs
Asacoltablet, delayed release400 mg/1oralCardinal Health1992-04-01Not applicableUs
Asacoltablet, delayed release400 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Asacoltablet, delayed release400 mg/1oralCardinal Health1992-04-01Not applicableUs
Asacoltablet, delayed release400 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-23Not applicableUs
Asacoltablet, delayed release400 mg/1oralWarner Chilcott (US), LLC1992-04-01Not applicableUs
Asacoltablet, delayed release400 mg/1oralREMEDYREPACK INC.2012-03-30Not applicableUs
Asacoltablet, delayed release400 mg/1oralAmerican Health Packaging2012-01-232015-12-29Us
Asacoltablet, delayed release400 mg/1oralREMEDYREPACK INC.2011-03-09Not applicableUs
Asacol 800tablet (delayed-release)800 mgoralWarner Chilcott Canada Co2005-06-13Not applicableCanada
Asacol Hdtablet, delayed release800 mg/1oralWarner Chilcott (US), LLC2008-05-28Not applicableUs
Canasasuppository1000 mg/1rectalAptalis Pharma Us Inc2001-01-05Not applicableUs
Canasasuppository1000 mg/1rectalPhysicians Total Care, Inc.2010-08-18Not applicableUs
Delzicolcapsule, delayed release400 mg/1oralCarilion Materials Management2013-03-01Not applicableUs
Delzicolcapsule, delayed release400 mg/1oralWarner Chilcott (US), LLC2013-03-01Not applicableUs
Delzicolcapsule, delayed release400 mg/1oralWarner Chilcott (US), LLC2016-03-312016-04-13Us
Lialdatablet, delayed release1.2 g/1oralShire US Manufacturing Inc.2007-01-16Not applicableUs
Lialdatablet, delayed release1.2 g/1oralKAISER FOUNDATION HOSPITALS2013-12-06Not applicableUs
Mesalaminesuspension4 g/60mLrectalFranklin Pharmaceutical LLC2010-04-01Not applicableUs
Mesalaminecapsule500 mg/1oralPrasco Laboratories2004-07-08Not applicableUs
Mesalaminecapsule250 mg/1oralPrasco Laboratories1993-05-10Not applicableUs
Mesasaltablet (enteric-coated)500 mgoralGlaxosmithkline Inc1992-12-31Not applicableCanada
Mezavanttablet (delayed and extended release)1.2 goralShire Pharma Canada Ulc2007-07-27Not applicableCanada
Ntp-5-aminosalicylic Acidtablet (enteric-coated)400 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Pendo-5 Asatablet (enteric-coated)400 mgoralPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
Pentasacapsule250 mg/1oralShire US Manufacturing Inc.1993-05-10Not applicableUs
Pentasacapsule500 mg/1oralREMEDYREPACK INC.2011-10-04Not applicableUs
Pentasacapsule250 mg/1oralCardinal Health1993-05-10Not applicableUs
Pentasacapsule250 mg/1oralCarilion Materials Management1993-05-10Not applicableUs
Pentasacapsule500 mg/1oralShire US Manufacturing Inc.2004-07-08Not applicableUs
Pentasatablet (extended-release)1.00 goralFerring Inc2013-03-12Not applicableCanada
Pentasacapsule250 mg/1oralAvera Mc Kennan Hospital2015-04-27Not applicableUs
Pentasa Enema 1g/100mlenema; liquid1 grectalFerring Inc1995-12-31Not applicableCanada
Pentasa Enema 2g/100mlenema; liquid2 grectalFerring Inc1995-12-312004-08-05Canada
Pentasa Enema 4g/100mlenema; liquid4 grectalFerring Inc1995-12-31Not applicableCanada
Pentasa Extended-release Tablets 250mgtablet (extended-release)250 mgoralFerring Inc1995-12-312004-08-05Canada
Pentasa Extended-release Tablets 500mgtablet (extended-release)500 mgoralFerring Inc1994-12-31Not applicableCanada
Pentasa Suppository - 1gsuppository1 grectalFerring Inc1995-12-31Not applicableCanada
Rowasaenema4 g/60mLrectalAlaven Pharmaceutical LLC1988-01-31Not applicableUs
Rowasasuspension4 g/60mLrectalMEDA Pharmaceuticals2016-03-29Not applicableUs
Salofalksuppository1000 mgrectalAptalis Pharma Canada Inc2000-06-01Not applicableCanada
Salofalktablet (enteric-coated)500 mgoralAptalis Pharma Canada Inc1995-12-31Not applicableCanada
Salofalksuppository500 mgrectalAptalis Pharma Canada Inc1995-12-31Not applicableCanada
Salofalksuspension2 grectalAptalis Pharma Canada Inc1995-12-31Not applicableCanada
Salofalksuspension4 grectalAptalis Pharma Canada Inc1995-12-31Not applicableCanada
Salofalk (r) 5-asa Enteric Coated Tab- 250mgtablet (enteric-coated)250 mgoralAxcan Pharma Inc1995-12-311998-08-03Canada
Salofalk (r) 5-asa Suppositories - 250mgsuppository250 mgrectalAxcan Pharma Inc1995-12-312006-09-12Canada
Sf Rowasasuspension4 g/60mLrectalAlaven Pharmaceutical LLC2009-09-01Not applicableUs
Sfrowasa Sulfite-free Formulationsuspension4 g/60mLrectalMEDA Pharmaceuticals2016-03-29Not applicableUs
Teva-5 Asatablet (enteric-coated)400 mgoralTeva Canada Limited1995-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mesalamineenema4 g/60mLrectalGAVIS Pharmaceuticals, LLC2009-12-16Not applicableUs
MesalaminekitPerrigo New York Inc2009-09-01Not applicableUs
Mesalamineenema4 g/60mLrectalPerrigo New York Inc2007-10-11Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AsacolitinNot Available
ClaversalNot Available
FisalamineNot Available
LixacolNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII4Q81I59GXC
CAS number89-57-6
WeightAverage: 153.1354
Monoisotopic: 153.042593095
Chemical FormulaC7H7NO3
InChI KeyInChIKey=KBOPZPXVLCULAV-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
IUPAC Name
5-amino-2-hydroxybenzoic acid
SMILES
NC1=CC(C(O)=O)=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • 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 active ulcerative proctitis.
PharmacodynamicsMesalazine (INN, BAN), also known as Mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism.
Mechanism of actionAlthough the mechanism of action of mesalazine is not fully understood, it appears to be topical rather than systemic. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes and hydroxyeicosatetraenoic acids, is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalazine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin production in the colon.
Related Articles
Absorption20 to 30% absorbed following oral administration. 10 to 35% absorbed from the colon (rectal suppository) - extent of absorption is determined by the length of time the drug is retained in the colon.
Volume of distributionNot Available
Protein bindingAbout 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound.
Metabolism

Rapidly and extensively metabolized, mainly to N-acetyl-5-ASA (Ac-5-ASA) in the intestinal mucosal wall and the liver. Ac-5-ASA is further acetylated (deactivated) in at least 2 sites, the colonic epithelium and the liver.

SubstrateEnzymesProduct
Mesalazine
Not Available
N-acetyl-5-ASA (Ac-5-ASA)Details
Route of eliminationApproximately 28% of the mesalamine in Asacol tablets is absorbed after oral ingestion, leaving the remainder available for topical action and excretion in the feces. It is excreted mainly by the kidney as N-acetyl-5-aminosalicylic acid.
Half lifeThe mean elimination half-life was 5 hours for 5-ASA and six hours for N-acetyl-5-ASA following the initial dose. At steady state, the mean elimination half-life was seven hours for both 5-ASA and N-acetyl-5-ASA.
ClearanceNot Available
ToxicityOral, mouse: LD50 = 3370 mg/kg; Oral, rat: LD50 = 2800 mg/kg; Skin, rabbit: LD50 = >5 gm/kg. There have been no documented reports of serious toxicity in man resulting from massive overdosing with mesalamine. Under ordinary circumstances, mesalazine absorption from the colon is limited.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9471
Blood Brain Barrier-0.6168
Caco-2 permeable-0.8829
P-glycoprotein substrateNon-substrate0.8186
P-glycoprotein inhibitor INon-inhibitor0.985
P-glycoprotein inhibitor IINon-inhibitor0.9912
Renal organic cation transporterNon-inhibitor0.9314
CYP450 2C9 substrateNon-substrate0.8284
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.7636
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.8712
CYP450 2D6 inhibitorNon-inhibitor0.9744
CYP450 2C19 inhibitorInhibitor0.6752
CYP450 3A4 inhibitorNon-inhibitor0.6628
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9023
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7922
BiodegradationReady biodegradable0.6197
Rat acute toxicity1.7065 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9759
hERG inhibition (predictor II)Non-inhibitor0.9715
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Salix pharmaceuticals inc
  • Shire development inc
  • Perrigo israel pharmaceuticals ltd
  • Teva pharmaceuticals usa inc
  • Alaven pharmaceutical llc
  • Axcan pharma us inc
  • Warner chilcott pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseoral375 mg/1
Tabletoral400 mg/1
Tablet (enteric-coated)oral400 mg
Tablet, delayed releaseoral400 mg/1
Tablet (delayed-release)oral800 mg
Tablet, delayed releaseoral800 mg/1
Suppositoryrectal1000 mg/1
Capsule, delayed releaseoral400 mg/1
Tablet, delayed releaseoral1.2 g/1
Enemarectal4 g/60mL
Kit
Suspensionrectal4 g/60mL
Tablet (enteric-coated)oral500 mg
Tablet (delayed and extended release)oral1.2 g
Capsuleoral250 mg/1
Capsuleoral500 mg/1
Tablet (extended-release)oral1.00 g
Enema; liquidrectal1 g
Enema; liquidrectal2 g
Enema; liquidrectal4 g
Tablet (extended-release)oral250 mg
Tablet (extended-release)oral500 mg
Suppositoryrectal1 g
Suppositoryrectal1000 mg
Suppositoryrectal500 mg
Suspensionrectal2 g
Suspensionrectal4 g
Tablet (enteric-coated)oral250 mg
Suppositoryrectal250 mg
Prices
Unit descriptionCostUnit
Canasa 30 1000 mg Suppository Box488.32USD box
Canasa 1000 mg suppository13.88USD suppository
Salofalk (4 g/60 g) 4 g/enm Enema6.73USD enema
Canasa 500 mg suppository6.24USD suppository
Pentasa (4 g/100 Ml) 4 g/enm Enema5.02USD enema
Pentasa (1 g/100Ml) 1 g/enm Enema4.17USD enema
Salofalk (2 g/60 g) 2 g/enm Enema3.96USD enema
Asacol hd dr 800 mg tablet3.88USD tablet
Pentasa 500 mg capsule2.66USD capsule
Asacol 400 mg Enteric Coated Tabs2.22USD tab
Asacol ec 400 mg tablet1.94USD tablet
Salofalk 1000 mg Suppository1.81USD suppository
Pentasa 1 g Suppository1.8USD suppository
Salofalk 500 mg Suppository1.23USD suppository
Asacol 800 800 mg Enteric-Coated Tablet1.14USD tablet
Pentasa 250 mg capsule1.07USD capsule
Mesasal 500 mg Enteric-Coated Tablet0.69USD tablet
Pentasa 500 mg Sustained-Release Tablet0.63USD tablet
Asacol 400 mg Enteric-Coated Tablet0.59USD tablet
Salofalk 500 mg Enteric-Coated Tablet0.56USD tablet
Novo-5 Asa 400 mg Enteric-Coated Tablet0.42USD tablet
Rowasa 4 gm/60 ml enema0.41USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2111697 No2002-08-202012-06-16Canada
CA2444814 No2009-06-092021-10-24Canada
US5541170 No1993-07-302013-07-30Us
US6551620 No1998-04-202018-04-20Us
US6649180 No2000-04-132020-04-13Us
US6773720 No2000-06-082020-06-08Us
US6893662 No2001-11-152021-11-15Us
US7645801 No2007-07-242027-07-24Us
US8217083 No2008-06-062028-06-06Us
US8337886 No1998-04-202018-04-20Us
US8436051 No2008-06-062028-06-06Us
US8496965 No1998-04-202018-04-20Us
US8580302 No2001-11-152021-11-15Us
US8865688 No2010-05-012030-05-01Us
US8911778 No1998-04-202018-04-20Us
US8940328 No1998-04-202018-04-20Us
US8956647 No1998-04-202018-04-20Us
US9089492 No2001-11-152021-11-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point283 °CPhysProp
water solubility0.84 g/L at 20°CNot Available
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.2 mg/mLALOGPS
logP0.75ALOGPS
logP-0.29ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.02ChemAxon
pKa (Strongest Basic)5.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m3·mol-1ChemAxon
Polarizability14.26 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.48 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 References
  1. Link [Link]
External Links
ATC CodesA07EC02
AHFS Codes
  • 56:36.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (67.7 KB)
Interactions
Drug Interactions
Drug
Aluminum hydroxideThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Aluminum hydroxide.
ArdeparinThe risk or severity of adverse effects can be increased when Mesalazine is combined with Ardeparin.
Calcium carbonateThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Calcium carbonate.
CimetidineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Cimetidine.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Mesalazine.
EsomeprazoleThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Esomeprazole.
FamotidineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Famotidine.
HeparinThe risk or severity of adverse effects can be increased when Mesalazine is combined with Heparin.
InfliximabInfliximab may increase the nephrotoxic activities of Mesalazine.
LansoprazoleThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Lansoprazole.
Magnesium hydroxideThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Magnesium hydroxide.
Magnesium oxideThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Magnesium oxide.
NizatidineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Nizatidine.
OmeprazoleThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Omeprazole.
PantoprazoleThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Pantoprazole.
RabeprazoleThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Rabeprazole.
RanitidineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Ranitidine.
Sodium bicarbonateThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Sodium bicarbonate.
TioguanineThe metabolism of Tioguanine can be decreased when combined with Mesalazine.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
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
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. 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 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
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
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation...
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, Chavatte P, Farce A, Bulois P, Cortot A, Colombel JF, Desreumaux P: Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 2005 Apr 18;201(8):1205-15. Epub 2005 Apr 11. [PubMed:15824083 ]
  2. Schwab M, Reynders V, Loitsch S, Shastri YM, Steinhilber D, Schroder O, Stein J: PPARgamma is involved in mesalazine-mediated induction of apoptosis and inhibition of cell growth in colon cancer cells. Carcinogenesis. 2008 Jul;29(7):1407-14. doi: 10.1093/carcin/bgn118. Epub 2008 Jun 9. [PubMed:18544567 ]
  3. Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [PubMed:18077625 ]
  4. Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [PubMed:16939423 ]
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:
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 2 critical serine residues. These mo...
Gene Name:
IKBKB
Uniprot ID:
O14920
Molecular Weight:
86563.245 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
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. Nandi J, Saud B, Zinkievich JM, Palma DT, Levine RA: 5-aminosalicylic acid improves indomethacin-induced enteropathy by inhibiting iNOS transcription in rats. Dig Dis Sci. 2008 Jan;53(1):123-32. Epub 2007 May 15. [PubMed:17503181 ]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
nat
Uniprot ID:
P0A5L8
Molecular Weight:
Not Available
References
  1. Tucker MA, Smith TJ: Acetylation of 5-aminosalicylate by hamster colon arylamine N-acetyltransferase. J Appl Toxicol. 1990 Feb;10(1):73-4. [PubMed:2335716 ]
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Drug created on June 13, 2005 07:24 / Updated on July 26, 2016 01:53