Identification

Name
Mesalazine
Accession Number
DB00244  (APRD01098, DB05376, DB06396)
Type
Small Molecule
Groups
Approved
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
  • m-Aminosalicylic acid
  • Mesalamine
  • Mesalazina
  • Mésalazine
  • Mesalazinum
  • p-Aminosalicylsaeure
External IDs
MAX-002 / SPD476
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
5-asaTablet, delayed release400 mgOralSanis Health Inc2010-11-022012-08-03Canada
AprisoCapsule, extended release375 mg/1OralAphena Pharma Solutions Tennessee, Inc.2008-10-31Not applicableUs
AprisoCapsule, extended release375 mg/1OralPhysicians Total Care, Inc.2010-08-18Not applicableUs54868 615020180907 15195 wm2d6v
AprisoCapsule, extended release375 mg/1OralSalix Pharmaceuticals, Inc.2008-10-31Not applicableUs65649 0103 02 nlmimage10 eb39758b
AsacolTablet, delayed release400 mg/1OralPhysicians Total Care, Inc.2002-05-102011-06-30Us
AsacolTablet, delayed release400 mg/1OralKaiser Foundations Hospitals2012-02-23Not applicableUs
AsacolTablet, delayed release400 mg/1OralREMEDYREPACK INC.2012-03-302016-10-07Us
AsacolTablet, delayed release400 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs53808 020520180907 15195 1lcm2eh
AsacolTablet, delayed release400 mg/1OralAmerincan Health Packaging2012-01-232012-02-29Us
AsacolTablet, delayed release400 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2012-03-232013-03-20Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MesalamineEnema4 g/60mLRectalGavis Pharmaceuticals, LLC.2009-12-16Not applicableUs
MesalamineTablet, delayed release800 mg/1OralZydus Pharmaceuticals Usa, Inc.2016-08-01Not applicableUs
MesalamineTablet, delayed release800 mg/1OralA-S Medication Solutions2016-08-01Not applicableUs
MesalamineKit4 g/60mLPerrigo New York Inc.2009-09-01Not applicableUs
MesalamineTablet, delayed release800 mg/1OralAmerincan Health Packaging2016-11-182019-02-28Us
MesalamineTablet, delayed release1.2 g/1OralAmerican Health Packaging2018-09-01Not applicableUs
MesalamineTablet, delayed release800 mg/1OralCadila Pharnmaceuticals2018-08-02Not applicableUs
MesalamineEnema4 g/60mLRectalANI Pharmaceuticals, Inc.2016-05-13Not applicableUs
MesalamineTablet, delayed release1.2 g/1OralShire2017-08-29Not applicableUs
MesalamineSuspension4 g/60mLRectalFranklin Pharmaceutical LLC2010-04-012018-01-01Us
International/Other Brands
Asacol / Asacolitin / Canasa / Claversal / Fisalamine / Iialda / Lixacol / Mesasal / Pentasa / Rowasa / Salofalk
Categories
UNII
4Q81I59GXC
CAS number
89-57-6
Weight
Average: 153.1354
Monoisotopic: 153.042593095
Chemical Formula
C7H7NO3
InChI Key
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

Pharmacology

Indication

For the treatment of active ulcerative proctitis.

Associated Conditions
Pharmacodynamics

Mesalazine (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 action

Although 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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
AProstaglandin G/H synthase 1
inhibitor
Human
AArachidonate 5-lipoxygenase
inhibitor
Human
APeroxisome proliferator-activated receptor gamma
agonist
Human
UInhibitor of nuclear factor kappa-B kinase subunit alpha
inhibitor
Human
UInhibitor of nuclear factor kappa-B kinase subunit beta
inhibitor
Human
UMyeloperoxidaseNot AvailableHuman
UArylamine N-acetyltransferaseNot AvailableMycobacterium tuberculosis
Absorption

20 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 distribution
Not Available
Protein binding

About 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.

Route of elimination

Approximately 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 life

The 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.

Clearance
Not Available
Toxicity

Oral, 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Mesalazine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Mesalazine is combined with (S)-Warfarin.
2,4-thiazolidinedioneMesalazine may increase the hypoglycemic activities of 2,4-thiazolidinedione.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Mesalazine is combined with 4-hydroxycoumarin.
AbacavirMesalazine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding can be increased when Mesalazine is combined with Abciximab.
AcarboseMesalazine may increase the hypoglycemic activities of Acarbose.
AcebutololMesalazine may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Mesalazine.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Mesalazine.
Food Interactions
  • Take without regard to meals.

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
Human Metabolome Database
HMDB0014389
KEGG Drug
D00377
PubChem Compound
4075
PubChem Substance
46509142
ChemSpider
3933
BindingDB
60918
ChEBI
6775
ChEMBL
CHEMBL704
Therapeutic Targets Database
DAP000729
PharmGKB
PA450384
IUPHAR
2700
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Mesalazine
ATC Codes
A07EC02 — Mesalazine
AHFS Codes
  • 56:36.00 — Anti-inflammatory Agents
MSDS
Download (67.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableUlcerative Colitis (UC)1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceUlcerative Colitis (UC)3
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentUlcerative Colitis (UC)1
1TerminatedNot AvailableUlcerative Colitis (UC)1
1, 2Active Not RecruitingTreatmentHelminth Infection / Protozoan Infections / Ulcerative Colitis (UC) / Ulcerative Colitis Exacerbation1
1, 2CompletedTreatmentChronic Beryllium Disease (CBD)1
1, 2CompletedTreatmentMalnutrition1
2CompletedPreventionSporadic Colorectal Adenoma1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentDiverticulitis1
2CompletedTreatmentDiverticulosis, Colonic1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)2
2CompletedTreatmentProctitis1
2CompletedTreatmentUlcerative Colitis (UC)2
2Not Yet RecruitingPreventionColorectal Neoplasms, Hereditary Nonpolyposis1
2RecruitingPreventionColorectal Cancers1
2RecruitingTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
2WithdrawnTreatmentColitis / Cytokines / Drug Evaluation / Hermanski-Pudlak Syndrome / Lymphocytes1
2, 3CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2, 3CompletedTreatmentMicroscopic Colitis / Severe or persistent diarrhea1
3Active Not RecruitingTreatmentUlcerative Colitis (UC)1
3CompletedNot AvailableMild to Moderate Ulcerative Colitis1
3CompletedPreventionCrohn's Disease (CD)1
3CompletedPreventionDiverticular disorders1
3CompletedPreventionDiverticulitis2
3CompletedPreventionRecurrences / Ulcerative Colitis (UC)1
3CompletedPreventionUlcerative Colitis (UC)2
3CompletedTreatmentCollagenous Colitis1
3CompletedTreatmentCrohn's Disease (CD)2
3CompletedTreatmentIrritable Bowel Syndrome (IBS)1
3CompletedTreatmentLymphocytic Colitis1
3CompletedTreatmentRemission of Ulcerative Colitis / Ulcerative Colitis, Active1
3CompletedTreatmentUlcerative Colitis (UC)19
3CompletedTreatmentUlcerative Colitis Acute1
3CompletedTreatmentUlcerative Colitis in Remission1
3CompletedTreatmentUlcerative Colitis, Active1
3Not Yet RecruitingTreatmentChronic, moderate Ulcerative Colitis / Ulcerative Colitis Chronic Mild1
3RecruitingTreatmentCrohn's Disease (CD) / Oral Ulcers1
3RecruitingTreatmentIrritable Bowel Syndrome (IBS)1
3RecruitingTreatmentUlcerative Colitis (UC)6
3TerminatedPreventionDiverticulitis2
3TerminatedTreatmentCrohn's Disease (CD)2
3TerminatedTreatmentProctitis1
3TerminatedTreatmentUlcerative Colitis (UC)2
3TerminatedTreatmentUlcerative Proctitis1
4CompletedDiagnosticUlcerative Colitis (UC)1
4CompletedPreventionUlcerative Colitis (UC)1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Immune System Diseases / Lentivirus Infections / Sexually Transmitted Disease (STD)1
4CompletedTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
4CompletedTreatmentDiverticular Disease of the Colon1
4CompletedTreatmentIrritable Bowel Syndrome With Diarrhoea1
4CompletedTreatmentMild to Moderate Ulcerative Colitis1
4CompletedTreatmentUlcerative Colitis (UC)2
4RecruitingTreatmentCrohn's Disease (CD)1
4RecruitingTreatmentUlcerative Colitis (UC)1
4TerminatedTreatmentCrohn's Disease (CD)1
4Unknown StatusTreatmentIntestinal LNH1
4WithdrawnTreatmentDiarrhoea Predominant Irritable Bowel Syndrome / Quality of Life1
Not AvailableActive Not RecruitingNot AvailableUlcerative Colitis (UC)1
Not AvailableActive Not RecruitingBasic ScienceLocal Drug Concentration in Gastrointestinal Tract1
Not AvailableCompletedNot AvailableActive Ulcerative Proctitis / Distal Ulcerative Colitis1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentInflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
Not AvailableRecruitingSupportive CareUlcerative Colitis (UC)1
Not AvailableRecruitingTreatmentAminosalicylic Acid / Ulcerative Colitis (UC)1
Not AvailableTerminatedTreatmentUlcerative Colitis (UC)1
Not AvailableUnknown StatusNot AvailableSimple Diverticular Disease1

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
  • Alaven Pharmaceutical
  • Amerisource Health Services Corp.
  • Anip Acquisition Co.
  • Atlantic Biologicals Corporation
  • Axcan Pharma Inc.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Cosmo SPA
  • Dept Health Central Pharmacy
  • Diversified Healthcare Services Inc.
  • Ferring Pharmaceuticals Inc.
  • Franklin Pharmaceutical LLC
  • Gavis Pharmaceuticals LLC
  • Heartland Repack Services LLC
  • Infar SA
  • Letco Medical Inc.
  • Norwich Pharmaceuticals Inc.
  • Paddock Labs
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Physicians Total Care Inc.
  • Prasco Labs
  • Prepak Systems Inc.
  • Resource Optimization and Innovation LLC
  • Salix Pharmaceuticals
  • Sanofi-Aventis Inc.
  • Shire Inc.
  • Solvay Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
  • Warner Chilcott Co. Inc.
  • WC Pharmaceuticals
  • Wellspring Pharmaceutical
Dosage forms
FormRouteStrength
Tablet, delayed releaseOral400 mg
Capsule, extended releaseOral375 mg/1
TabletOral400 mg/1
Tablet, delayed releaseOral400 mg/1
Tablet, delayed releaseOral800 mg
Tablet, delayed releaseOral800 mg/1
SuppositoryRectal1000 mg/1
Capsule, delayed releaseOral400 mg/1
Tablet, delayed releaseOral1.2 g/1
CapsuleOral250 mg/1
CapsuleOral500 mg/1
EnemaRectal4 g/60mL
Kit4 g/60mL
SuspensionRectal4 g/60mL
Tablet, extended releaseOral1.2 g
KitRectal1 g
SuspensionRectal1 g
SuspensionRectal4 g
Tablet, extended releaseOral1 g
Enema; liquidRectal2 g
Tablet, extended releaseOral250 mg
Tablet, extended releaseOral500 mg
SuppositoryRectal1 g
SuppositoryRectal500 mg
SuspensionRectal2 g
Tablet, delayed releaseOral500 mg
Tablet, delayed releaseOral250 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)
US5541170No1993-07-302013-07-30Us
CA2444814No2009-06-092021-10-24Canada
CA2111697No2002-08-202012-06-16Canada
US7645801No2007-07-242027-07-24Us
US6773720No2000-06-082020-06-08Us
US8436051No2008-06-062028-06-06Us
US8217083No2008-06-062028-06-06Us
US6893662No2001-11-152021-11-15Us
US8580302No2001-11-152021-11-15Us
US9089492No2001-11-152021-11-15Us
US8911778No1998-04-202018-04-20Us
US6551620No1998-04-202018-04-20Us
US8337886No1998-04-202018-04-20Us
US8865688No2010-05-012030-05-01Us
US8496965No1998-04-202018-04-20Us
US8940328No1998-04-202018-04-20Us
US8956647No1998-04-202018-04-20Us
US6649180No2000-04-132020-04-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)283 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (8.48 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-0900000000-db75ae2d436dd6156c91

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzoic acids
Alternative Parents
Salicylic acids / Benzoic acids / p-Aminophenols / Benzoyl derivatives / Aniline and substituted anilines / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids
show 5 more
Substituents
Aminobenzoic acid / Hydroxybenzoic acid / Salicylic acid or derivatives / Salicylic acid / Benzoic acid / P-aminophenol / Aminophenol / Benzoyl / Aniline or substituted anilines / 1-hydroxy-2-unsubstituted benzenoid
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, phenols, aromatic amine, amino acid, monohydroxybenzoic acid (CHEBI:6775)

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...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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
Uniprot Name
Arachidonate 5-lipoxygenase
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...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
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 oth...
Gene Name
CHUK
Uniprot ID
O15111
Uniprot Name
Inhibitor of nuclear factor kappa-B kinase subunit alpha
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 oth...
Gene Name
IKBKB
Uniprot ID
O14920
Uniprot Name
Inhibitor of nuclear factor kappa-B kinase subunit beta
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 o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
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
Catalyzes the transfer of the acetyl group from acetyl coenzyme A to the free amino group of arylamines and hydrazines (PubMed:18795795). Is able to utilize not only acetyl-CoA, but also n-propionyl-CoA and acetoacetyl-CoA as acyl donors, although at a lower rate (PubMed:19014350). As acetyl-CoA and propionyl-CoA are products of cholesterol catabolism and the nat gene is likely present in the same operon than genes involved in cholesterol degradation, this enzyme could have a role in the utilization and regulation of these CoA species (PubMed:19014350).
Specific Function
Arylamine n-acetyltransferase activity
Gene Name
nat
Uniprot ID
P9WJI5
Uniprot Name
Arylamine N-acetyltransferase
Molecular Weight
31028.88 Da
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]

Drug created on June 13, 2005 07:24 / Updated on November 12, 2018 07:13