Mesalazine

Identification

Summary

Mesalazine is an aminosalicylate drug used to treat mild to moderate active ulcerative colitis and also to maintain remission once achieved.

Brand Names
Apriso, Asacol, Canasa, Delzicol, Lialda, Mezavant, Pentasa, Rowasa, Salofalk, Zaldyon
Generic Name
Mesalazine
DrugBank Accession Number
DB00244
Background

An anti-inflammatory agent, structurally related to the salicylates and non-steroidal anti-inflammatory drugs like acetylsalicylic acid, which is active in inflammatory bowel disease 2. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed) Although demonstrably effective in treating and maintaining remission for ulcerative colitis, mesalazine has historically faced a number of issues regarding its lack of stability as a pharmaceutical agent 1. Throughout the late seventies and the eighties, important research initiatives developed stable mesalazine formulations like the eudragit-S coating of Asacol brand mesalazine and the Pentasa brand's encapsulation of mesalazine within microgranules 1. In the present day, contemporary research regarding novel methods to stabilize mesalazine continues and interest in the agent's capacity to decrease inflammatory activity and subsequently potentially reduce the risk of colorectal cancer in conditions like ulcerative colitis is maintained 1,2.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 153.1354
Monoisotopic: 153.042593095
Chemical Formula
C7H7NO3
Synonyms
  • 3-carboxy-4-hydroxyaniline
  • 5-aminosalicylic acid
  • 5-ASA
  • m-Aminosalicylic acid
  • Mesalamine
  • Mesalazina
  • Mésalazine
  • Mesalazine
  • Mesalazinum
  • p-Aminosalicylsaeure
External IDs
  • MAX-002
  • SPD476

Pharmacology

Indication

Mesalazine is indicated for the induction of remission in patients with active or mild to moderate acute exacerbations of ulcerative colitis and for the maintenance of remission of ulcerative colitis Label, 3. Prescribing information for mesalazine in the UK also indicates the medication for the maintenance of remission of Crohn's ileo-colitis 3.

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Associated Conditions
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Pharmacodynamics

Mesalazine is one of the two components of sulphasalazine, the other being sulphapyridine. It is the latter which is responsible for the majority of the side effects associated with sulphasalazine therapy whilst mesalazine is known to be the active moiety in the treatment of ulcerative colitis 3.

The pharmacodynamic actions of mesalazine occur in the colonic/rectal mucosae local to the delivery of drug from mesalazine tablets into the lumen Label. There is information suggesting that the severity of colonic inflammation in ulcerative colitis patients treated with mesalazine is inversely correlated with mucosal concentrations of mesalazine Label. Plasma concentrations representing systemically absorbed mesalazine are not believed to contribute extensively to efficacy Label.

Mechanism of action

Although the mechanism of action of mesalazine is not fully understood, it is believed to possess a topical anti-inflammatory effect on colonic epithelial cells Label. 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 Label.

Furthermore, mesalazine also has the potential to inhibit the activation of Nuclear Factor kappa B (NKkB) and consequently the production of key of pro-inflammatory cytokines Label. It has been proposed that reduced expression of PPAR gamma nuclear receptors (gamma form of peroxisome proliferator-activated receptors) may be implicated in ulcerative colitis Label. There is evidence that mesalazine produces pharmacodynamic effects through direct activation of PPAR gamma receptors in the colonic/rectal epithelium as well Label.

Moreover, since increased leukocyte migration, abnormal cytokine production, increased production of arachidonic acid metabolites, particularly leukotriene B4, and increased free radical formation in the inflamed intestinal tissue are all present in patients with inflammatory bowel disease it is also believed that mesalazine has in-vitro and in-vivo pharmacological effects that inhibit leukocyte chemotaxis, decrease cytokine and leukotriene production and scavenge for free radicals 4.

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

Depending on the formulation administered, prescribing information for orally administered delayed-released tablets of 2.4g or 4.8g of mesalazine given once daily for 14 days to healthy volunteers was to found to be about 21% to 22% of the administered dose Label while prescribing information for an orally administered controlled-release capsule formulation suggests 20% to 30% of the mesalazine in the formulation is absorbed 9. In contrast, when mesalamine is administered orally as an unformulated 1-g aqueous suspension, mesalazine is approximately 80% absorbed 9.

Volume of distribution

The apparent volume of distribution (Vd) of the drug in adults is approximately 0.2 L/kg 5.

Protein binding

Mesalazine is approximately 43% bound to plasma proteins Label, 5.

Metabolism

The primary metabolite of mesalazine (5-aminosalicylic acid) is predominantly N-acetyl-5-aminosalicylic acid (Ac-5-ASA) Label. This metabolite is generated via N-acetyltransferase (NAT) activity in the liver and intestinal mucosa cells, largely by NAT-1, in particular Label.

Hover over products below to view reaction partners

Route of elimination

Elimination of mesalazine is mainly via the renal route following metabolism to N-acetyl-5-aminosalicylic acid (acetylation) Label. However, there is also limited excretion of the parent mesalazine drug in the urine Label.

After the oral administration of the extended-release formulation of mesalazine, of the approximately 21% to 22% of the drug absorbed, less than 8% of the dose was excreted unchanged in the urine after 24 hours, compared with greater than 13% for N-acetyl-5-aminosalicylic acid Label.

When given the controlled-release formulation, about 130 mg free mesalazine was recovered in the feces following a single 1-g dose, which was comparable to the 140 mg of mesalazine recovered from the molar equivalent sulfasalazine tablet dose of 2.5 g F3001]. Elimination of free mesalazine and salicylates in feces increased proportionately with the dose given. N-acetylmesalazine was the primary compound excreted in the urine (19% to 30%) following the controlled-release dosing 9.

Half-life

The apparent elimination half-life documented for oral delayed-release mesalazine tablets is 7 to 12 hours 5. The elimination half-life recorded for the active N-acetyl-5-aminosalicylic acid metabolite generated from the administration of oral delayed-release mesalazine tablets is 12 to 23 hours 5.

Clearance

The mean (SD) renal clearance in L/h for mesalazine following the single dose administration of mesalazine delayed-release tablets 4.8g under fasting conditions to young and elderly subjects was documented as 2.05 (1.33) in young subjects aged 18 to 35 years old, 2.04 (1.16) in elderly subjects aged 65 to 75 years old, and 2.13 (1.20) in elderly subjects older than 75 years Label.

Adverse Effects
Adverseeffects
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Toxicity

Oral, mouse: LD50 = 3370 mg/kg; Oral, rat: LD50 = 2800 mg/kg; Skin, rabbit: LD50 = >5 gm/kg MSDS.

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. Although there is little to no clinical experience with mesalazine overdosage Label. Mesalazine is an aminosalicylate, and symptoms of salicylate toxicity may be possible, such as tinnitus, vertigo, headache, confusion, drowsiness, sweating, hyperventilation, vomiting, and diarrhea Label. Severe intoxication with salicylates can lead to disruption of electrolyte balance and blood-pH, hyperthermia, and dehydration Label.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirMesalazine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage 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 therapeutic efficacy of Mesalazine can be decreased when used in combination with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Mesalazine is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Mesalazine is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Mesalazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Mesalazine is combined with Acetazolamide.
AcetohexamideMesalazine may increase the hypoglycemic activities of Acetohexamide.
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Product Images
International/Other Brands
Asacolitin / Claversal / Fisalamine / Iialda / Lixacol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
5-asaTablet, delayed release400 mgOralSanis Health Inc2010-11-022012-08-03Canada flag
AprisoCapsule, extended release375 mg/1OralAphena Pharma Solutions Tennessee, Inc.2008-10-31Not applicableUS flag
AprisoCapsule, extended release375 mg/1OralPhysicians Total Care, Inc.2010-08-18Not applicableUS flag54868 615020180907 15195 wm2d6v
AprisoCapsule, extended release375 mg/1OralSalix Pharmaceuticals, Inc.2008-10-31Not applicableUS flag65649 0103 02 nlmimage10 eb39758b
AsacolTablet, delayed release400 mg/1OralCardinal Health1992-04-012015-05-31US flag
AsacolTablet, delayed release400 mg/1OralCardinal Health1992-04-012012-12-31US flag55154 230520180907 15195 1ar9yvm
AsacolTablet, delayed release400 mgOralAllergan1993-12-312020-07-17Canada flag
AsacolTablet, delayed release400 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUS flag53808 020520180907 15195 1lcm2eh
AsacolTablet400 mg/1OralRemedy Repack2010-08-102012-02-16US flag00149 0752 15 nlmimage10 cf12e7c7
AsacolTablet, delayed release400 mg/1OralRemedy Repack2011-03-092016-11-28US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MesalamineTablet, delayed release1.2 g/1OralCadila Healthcare Limited2017-06-19Not applicableUS flag
MesalamineCapsule, extended release375 mg/1Oralbryant ranch prepack2021-01-05Not applicableUS flag
MesalamineEnema4 g/60mLRectalPadagis Israel Pharmaceuticals Ltd2007-10-11Not applicableUS flag
MesalamineTablet, delayed release1.2 g/1OralNorthstar Rx Llc.2018-06-25Not applicableUS flag
MesalamineTablet, delayed release800 mg/1OralZydus Pharmaceuticals (USA) Inc.2018-08-02Not applicableUS flag
MesalamineTablet, delayed release1.2 g/1OralActavis Pharma, Inc.2018-03-26Not applicableUS flag
MesalamineSuppository1000 mg/1RectalAmneal Pharmaceuticals NY LLC2020-01-08Not applicableUS flag
MesalamineSuppository1000 mg/1RectalZydus Pharmaceuticals (USA) Inc.2020-02-14Not applicableUS flag
MesalamineSuppository1000 mg/1RectalActavis Pharma, Inc.2021-04-23Not applicableUS flag
MesalamineTablet, delayed release800 mg/1OralAmerican Health Packaging2017-12-212020-01-31US flag

Categories

ATC Codes
A07EC02 — Mesalazine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / Amine / Amino acid / Amino acid or derivatives / Aminobenzoic acid / Aminophenol / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, phenols, aromatic amine, amino acid, monohydroxybenzoic acid (CHEBI:6775)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4Q81I59GXC
CAS number
89-57-6
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

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. Mayberry J: The history of 5-ASA compounds and their use in ulcerative colitis--trailblazing discoveries in gastroenterology. J Gastrointestin Liver Dis. 2013 Dec;22(4):375-7. [Article]
  2. Stolfi C, De Simone V, Pallone F, Monteleone G: Mechanisms of action of non-steroidal anti-inflammatory drugs (NSAIDs) and mesalazine in the chemoprevention of colorectal cancer. Int J Mol Sci. 2013 Sep 3;14(9):17972-85. doi: 10.3390/ijms140917972. [Article]
  3. Electronic Medicines Compendium: Asacol (mesalazine) 400mg MR Tablets Monograph [Link]
  4. Electronic Medicines Compendium: Pentasa (Mesalazine) Sachet 2g Monograph [Link]
  5. NIH Toxnet: Mesalazine Profile [Link]
  6. FDA Approved Drug Products: Asacol HD (mesalamine) delayed-release tablets for oral use [Link]
  7. FDA Approved Drug Products: Delzicol (mesalamine) delayed-release capsules for oral use [Link]
  8. FDA Approved Drug Products: Canasa (mesalamine) suppositories for rectal use [Link]
  9. Pentasa (Mesalazine) FDA Label [File]
Human Metabolome Database
HMDB0014389
KEGG Drug
D00377
PubChem Compound
4075
PubChem Substance
46509142
ChemSpider
3933
BindingDB
60918
RxNav
52582
ChEBI
6775
ChEMBL
CHEMBL704
ZINC
ZINC000000001688
Therapeutic Targets Database
DAP000729
PharmGKB
PA450384
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Mesalazine
FDA label
Download (1.61 MB)
MSDS
Download (67.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticUlcerative Colitis1
4CompletedPreventionUlcerative Colitis1
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 Colitis1
4CompletedTreatmentDiverticular Disease of the Colon1
4CompletedTreatmentIrritable Bowel Syndrome With Diarrhoea1
4CompletedTreatmentMild to Moderate Ulcerative Colitis1
4CompletedTreatmentUlcerative Colitis3
4Not Yet RecruitingTreatmentChildren / Exclusive Enteral Nutrition / Ulcerative Colitis1
4Not Yet RecruitingTreatmentChildren / Infliximab / Ulcerative Colitis1

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
Capsule, extended releaseOral375 mg/1
Aerosol, foamRectal1 G
Capsule, delayed releaseOral400 MG
Granule, for suspensionRectal2 G
SuspensionRectal2 G/50ML
SuspensionRectal4 G/50ML
TabletOral400 mg/1
Tablet, delayed releaseOral400 mg/1
Tablet, delayed releaseOral1600 MG
Tablet, delayed releaseOral
Tablet, delayed releaseOral800 mg/1
Tablet, coatedOral400 mg
Tablet, coatedOral800 mg
Aerosol, foamRectal2 G
Aerosol, foamRectal4 G
EnemaRectal2 G
EnemaRectal4 G
GelRectal500 MG
Granule, for suspensionRectal1.5 G
SuppositoryRectal400 MG
TabletOral400 MG
TabletOral800 MG
SuppositoryRectal
SuppositoryRectal1000 mg/1
SuppositoryRectal1 g
SuppositoryRectal0.5 g
SuspensionRectal4 g
SuspensionRectal2 g
SuspensionRectal4 G/60G
Tablet, film coatedOral
Granule, delayed releaseOral1.5 G
Capsule, delayed releaseOral400 mg/1
Tablet, coatedOral
Tablet, delayed releaseOral1.2 g/1
SuspensionRectal6.67 g
Tablet, coatedOral500 mg
Tablet, delayed releaseOral400 mg
SolutionRectal2 G
SolutionRectal4 G
Granule, delayed releaseOral
Capsule, extended releaseOral0.375 g/1
PowderNot applicable1 g/1g
SuspensionRectal4 g/60mL
GelRectal
PowderRectal
CapsuleOral400 MG
GelRectal2 G/60ML
GelRectal4 G/60ML
GelRectal10 %
Tablet, extended releaseOral1200 MG
SuspensionRectal7 g
Tablet, delayed releaseOral800 mg
SuspensionRectal6667 mg
Tablet, coatedOral505 mg
Tablet, extended releaseOral1.2 g
Tablet, delayed releaseOral1200 MG
Tablet, film coated, extended releaseOral
Tablet, delayed releaseOral1200.0 mg
KitRectal1 g / act
SuspensionRectal4 G/100ML
TabletOral1200 MG
CapsuleOral250 mg/1
CapsuleOral500 mg/1
GranuleOral1 G
SuspensionRectal1 g / 100 mL
SuspensionRectal1 G/100ML
SuspensionRectal2 G/100ML
SuspensionRectal4 g / 100 mL
TabletOral1 G
TabletOral250 MG
TabletOral500 MG
Tablet, extended releaseOral1 g
EnemaRectal1 g
EnemaRectal
SuppositoryRectal1.000 MG
SuspensionRectal1000 MG
Enema; liquidRectal2 g / 100 mL
Tablet, extended releaseOral250 mg
SuspensionRectal1 g/100 ml
Granule, delayed releaseOral1 g
Granule, delayed releaseOral2000 mg
Granule, delayed releaseOral4000 mg
Tablet, extended releaseOral1000 mg
Tablet, extended releaseOral
TabletOral1000 mg
SuspensionRectal0.01 g/ml
GranuleOral
TabletOral
Granule, delayed releaseOral4 G
SuppositoryRectal1000 mg
Granule, delayed releaseOral2 G
SuspensionRectal1 g
GranuleOral2000 mg
GranuleOral1000 mg
CapsuleOral
EnemaRectal4 g/60mL
SuspensionRectal2 g / 60 mL
SuspensionRectal4 g / 60 mL
EmulsionRectal1 g
GranuleOral3000 mg
Aerosol, foamRectal
Tablet, delayed releaseOral1 G
SuppositoryRectal250 mg
Tablet, delayed releaseOral250 mg
Tablet, coatedOral250 mg
SuspensionRectal2 G/30ML
SuspensionRectal
Tablet, delayed releaseOral500 mg
SuppositoryRectal500 mg
Granule, delayed releaseOral1000 mg
GranuleOral500 mg/1sachet
Granule, delayed releaseOral1500 mg
Granule, delayed releaseOral3000 mg
Granule, delayed releaseOral500 mg
Granule, delayed releaseOral3 G
GranuleOral1500 mg
GranuleOral500 mg
Tablet, extended releaseOral500 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)Region
US5541170No1996-07-302013-07-30US flag
CA2444814No2009-06-092021-10-24Canada flag
CA2111697No2002-08-202012-06-16Canada flag
US7645801No2010-01-122027-07-24US flag
US6773720No2004-08-102020-06-08US flag
US8436051No2013-05-072028-06-06US flag
US8217083No2012-07-102028-06-06US flag
US6893662No2005-05-172021-11-15US flag
US8580302No2013-11-122021-11-15US flag
US9089492No2015-07-282021-11-15US flag
US8911778No2014-12-162018-04-20US flag
US6551620No2003-04-222018-04-20US flag
US8337886No2012-12-252018-04-20US flag
US8865688No2014-10-212030-05-01US flag
US8496965No2013-07-302018-04-20US flag
US8940328No2015-01-272018-04-20US flag
US8956647No2015-02-172018-04-20US flag
US6649180No2003-11-182020-04-13US flag

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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT1
Uniprot ID
P18440
Uniprot Name
Arylamine N-acetyltransferase 1
Molecular Weight
33898.445 Da
References
  1. Mesalazine FDA Label [File]

Drug created on June 13, 2005 13:24 / Updated on October 19, 2021 07:39