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

Similar Structures

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

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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
UMyeloperoxidase	Not Available	Humans

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.

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Mesalazine
- N-acetyl-5-ASA (Ac-5-ASA)

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

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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.

Drug	Interaction
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Abacavir	Mesalazine may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding and hemorrhage can be increased when Mesalazine is combined with Abciximab.
Acarbose	Mesalazine may increase the hypoglycemic activities of Acarbose.
Acebutolol	Mesalazine may decrease the antihypertensive activities of Acebutolol.
Aceclofenac	The therapeutic efficacy of Mesalazine can be decreased when used in combination with Aceclofenac.
Acemetacin	The risk or severity of adverse effects can be increased when Mesalazine is combined with Acemetacin.
Acenocoumarol	The risk or severity of bleeding and hemorrhage can be increased when Mesalazine is combined with Acenocoumarol.
Acetaminophen	The risk or severity of adverse effects can be increased when Acetaminophen is combined with Mesalazine.
Acetazolamide	The risk or severity of adverse effects can be increased when Mesalazine is combined with Acetazolamide.
Acetohexamide	Mesalazine 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

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Product Images

International/Other Brands

Asacolitin / Claversal / Fisalamine / Iialda / Lixacol

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
5-asa	Tablet, delayed release	400 mg	Oral	Sanis Health Inc	2010-11-02	2012-08-03
Apriso	Capsule, extended release	375 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2008-10-31	Not applicable
Apriso	Capsule, extended release	375 mg/1	Oral	Salix Pharmaceuticals, Inc.	2008-10-31	Not applicable
Apriso	Capsule, extended release	375 mg/1	Oral	Physicians Total Care, Inc.	2010-08-18	Not applicable
Asacol	Tablet, delayed release	400 mg/1	Oral	Allergan	1992-04-01	2015-06-30
Asacol	Tablet, delayed release	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2013-01-01	Not applicable
Asacol	Tablet, delayed release	400 mg/1	Oral	Amerincan Health Packaging	2012-01-23	2012-02-29
Asacol	Tablet, delayed release	400 mg/1	Oral	KAISER FOUNDATION HOSPITALS	2012-02-23	2014-03-31
Asacol	Tablet, delayed release	400 mg/1	Oral	Physicians Total Care, Inc.	2002-05-10	2011-06-30
Asacol	Tablet, delayed release	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Mesalamine	Tablet, delayed release	800 mg/1	Oral	Zydus Pharmaceuticals (USA) Inc.	2018-08-02	Not applicable
Mesalamine	Capsule, extended release	0.375 g/1	Oral	Zydus Pharmaceuticals (USA) Inc.	2021-08-13	Not applicable
Mesalamine	Tablet, delayed release	800 mg/1	Oral	American Health Packaging	2017-12-21	2020-01-31
Mesalamine	Enema; Kit	4 g/60mL	Rectal	bryant ranch prepack	2009-09-01	Not applicable
Mesalamine	Suppository	1000 mg/1	Rectal	Rising Pharmaceuticals, Inc.	2019-06-05	Not applicable
Mesalamine	Tablet, delayed release	1.2 g/1	Oral	Mylan Pharmaceuticals Inc.	2018-12-14	Not applicable
Mesalamine	Capsule, delayed release	400 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2019-05-09	Not applicable
Mesalamine	Enema; Kit	4 g/60mL	Rectal	Padagis Israel Pharmaceuticals Ltd	2018-08-02	Not applicable
Mesalamine	Tablet, delayed release	800 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2016-08-01	Not applicable
Mesalamine	Capsule, extended release	500 mg/1	Oral	Sun Pharmaceutical Industries Inc.	2022-05-13	Not applicable

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

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]
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]
Electronic Medicines Compendium: Asacol (mesalazine) 400mg MR Tablets Monograph [Link]
Electronic Medicines Compendium: Pentasa (Mesalazine) Sachet 2g Monograph [Link]
NIH Toxnet: Mesalazine Profile [Link]
FDA Approved Drug Products: Asacol HD (mesalamine) delayed-release tablets for oral use [Link]
FDA Approved Drug Products: Delzicol (mesalamine) delayed-release capsules for oral use [Link]
FDA Approved Drug Products: Canasa (mesalamine) suppositories for rectal use [Link]
Pentasa (Mesalazine) FDA Label [File]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Completed	Diagnostic	Ulcerative Colitis	1
4	Completed	Prevention	Ulcerative Colitis	1
4	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Immune System Diseases / Lentivirus Infections / Sexually Transmitted Disease (STD)	1
4	Completed	Treatment	Crohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis	1
4	Completed	Treatment	Diverticular Disease of the Colon	1
4	Completed	Treatment	Irritable Bowel Syndrome With Diarrhoea	1
4	Completed	Treatment	Mild to Moderate Ulcerative Colitis	1
4	Completed	Treatment	Ulcerative Colitis	4
4	Not Yet Recruiting	Treatment	Biologics / Mesalazine / Self Efficacy / Ulcerative Colitis	1
4	Not Yet Recruiting	Treatment	Children / Exclusive Enteral Nutrition / Ulcerative Colitis	1

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

Form	Route	Strength
Capsule, extended release	Oral	375 mg/1
Capsule, delayed release	Oral	400 MG
Granule, for suspension	Rectal	2 G
Suspension	Rectal	2 G/50ML
Suspension	Rectal	4 G/50ML
Tablet	Oral	400 mg/1
Tablet, delayed release	Oral	400 mg/1
Tablet, delayed release	Oral
Tablet, delayed release	Oral	800 mg/1
Tablet, coated	Oral	400 mg
Tablet, coated	Oral	800 mg
Aerosol, foam	Rectal	2 G
Aerosol, foam	Rectal	4 G
Enema	Rectal	2 G
Enema	Rectal	4 G
Gel	Rectal	500 MG
Granule, for suspension	Rectal	1.5 G
Suppository	Rectal	400 MG
Tablet	Oral	400 MG
Tablet	Oral	800 MG
Suspension	Rectal
Tablet, delayed release	Oral	1000 mg
Suppository	Rectal	1000 mg/1
Suppository	Rectal	0.5 g
Suspension	Rectal	4 g
Suspension	Rectal	2 g
Suspension	Rectal	4 G/60G
Tablet, film coated	Oral	500 mg
Capsule, delayed release	Oral	400 mg/1
Tablet, coated	Oral
Tablet, delayed release	Oral	1.2 g/1
Suspension	Rectal	6.67 g
Tablet, coated	Oral	500 mg
Tablet, delayed release	Oral	400 mg
Solution	Rectal	2 G
Solution	Rectal	4 G
Capsule, extended release	Oral	0.375 g/1
Capsule, extended release	Oral	500 mg/1
Enema; kit	Rectal	4 g/60mL
Powder	Not applicable	1 g/1g
Suspension	Rectal	4 g/60mL
Aerosol, foam	Rectal
Gel	Rectal
Powder	Rectal
Capsule	Oral	400 MG
Gel	Rectal	2 G/60ML
Gel	Rectal	4 G/60ML
Gel	Rectal	10 %
Tablet, extended release	Oral	1200 MG
Suspension	Rectal	7 g
Tablet, delayed release	Oral	800 mg
Suspension	Rectal	6667 mg
Tablet, coated	Oral	505 mg
Tablet, extended release	Oral	1.2 g
Tablet, delayed release	Oral	1200 mg
Tablet, film coated, extended release	Oral
Tablet, delayed release	Oral	1200.0 mg
Kit	Rectal	1 g / act
Suspension	Rectal	4 G/100ML
Tablet	Oral	1200 MG
Capsule	Oral	250 mg/1
Capsule	Oral	500 mg/1
Suppository	Rectal
Suspension	Rectal	1 G/100ML
Suspension	Rectal	1 g / 100 mL
Suspension	Rectal	2 G/100ML
Suspension	Rectal	4 g / 100 mL
Tablet	Oral	250 MG
Tablet, extended release	Oral	1 g
Enema	Rectal	1 g
Enema	Rectal	1 g/100ml
Granule, delayed release	Oral
Suppository	Rectal	1.000 MG
Suspension	Rectal	1000 MG
Enema; liquid	Rectal	2 g / 100 mL
Tablet, extended release	Oral	250 mg
Suspension	Rectal	1 g/100 ml
Granule, delayed release	Oral	1 g
Granule, delayed release	Oral	2000 mg
Granule, delayed release	Oral	4000 mg
Tablet, extended release	Oral	1000 mg
Tablet, extended release	Oral
Tablet	Oral	1000 mg
Tablet	Oral	500 mg
Suspension	Rectal	0.01 g/ml
Granule	Oral	1 g
Tablet	Oral	1 g
Granule	Oral	2 g
Granule	Oral	4 g
Granule, delayed release	Oral	4 G
Granule	Oral
Suppository	Rectal	1 g
Suppository	Rectal	1000 mg
Granule, delayed release	Oral	2 G
Suspension	Rectal	1 g
Granule	Oral	2000 mg
Granule	Oral	1000 mg
Capsule	Oral
Enema	Rectal	4 g/60mL
Enema	Rectal
Granule	Oral	1500 MG
Suspension	Rectal	2 g / 60 g
Suspension	Rectal	4 g / 60 g
Tablet	Oral
Emulsion	Rectal	1 g
Granule	Oral	3000 mg
Aerosol, foam	Rectal	1 g
Granule	Oral	1.5 g
Granule, delayed release	Oral	1.5 g
Tablet, delayed release	Oral	1 G
Suppository	Rectal	250 mg
Tablet, delayed release	Oral	250 mg
Tablet, coated	Oral	250 mg
Suspension	Rectal	2 G/30ML
Granule	Oral	3 g
Granule, delayed release	Oral	3 g
Tablet, delayed release	Oral	500 mg
Suppository	Rectal	500 mg
Granule	Oral	500 mg
Granule, delayed release	Oral	1000 mg
Granule	Oral	500 mg/1sachet
Granule, delayed release	Oral	1500 mg
Granule, delayed release	Oral	3000 mg
Granule, delayed release	Oral	500 mg
Tablet	Oral	1600 MG
Tablet, delayed release	Oral	1600 mg
Tablet, extended release	Oral	500 mg

Prices

Unit description	Cost	Unit
Canasa 30 1000 mg Suppository Box	488.32USD	box
Canasa 1000 mg suppository	13.88USD	suppository
Salofalk (4 g/60 g) 4 g/enm Enema	6.73USD	enema
Canasa 500 mg suppository	6.24USD	suppository
Pentasa (4 g/100 Ml) 4 g/enm Enema	5.02USD	enema
Pentasa (1 g/100Ml) 1 g/enm Enema	4.17USD	enema
Salofalk (2 g/60 g) 2 g/enm Enema	3.96USD	enema
Asacol hd dr 800 mg tablet	3.88USD	tablet
Pentasa 500 mg capsule	2.66USD	capsule
Asacol 400 mg Enteric Coated Tabs	2.22USD	tab
Asacol ec 400 mg tablet	1.94USD	tablet
Salofalk 1000 mg Suppository	1.81USD	suppository
Pentasa 1 g Suppository	1.8USD	suppository
Salofalk 500 mg Suppository	1.23USD	suppository
Asacol 800 800 mg Enteric-Coated Tablet	1.14USD	tablet
Pentasa 250 mg capsule	1.07USD	capsule
Mesasal 500 mg Enteric-Coated Tablet	0.69USD	tablet
Pentasa 500 mg Sustained-Release Tablet	0.63USD	tablet
Asacol 400 mg Enteric-Coated Tablet	0.59USD	tablet
Salofalk 500 mg Enteric-Coated Tablet	0.56USD	tablet
Novo-5 Asa 400 mg Enteric-Coated Tablet	0.42USD	tablet
Rowasa 4 gm/60 ml enema	0.41USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5541170	No	1996-07-30	2013-07-30
CA2444814	No	2009-06-09	2021-10-24
CA2111697	No	2002-08-20	2012-06-16
US7645801	No	2010-01-12	2027-07-24
US6773720	No	2004-08-10	2020-06-08
US8436051	No	2013-05-07	2028-06-06
US8217083	No	2012-07-10	2028-06-06
US6893662	No	2005-05-17	2021-11-15
US8580302	No	2013-11-12	2021-11-15
US9089492	No	2015-07-28	2021-11-15
US8911778	No	2014-12-16	2018-04-20
US6551620	No	2003-04-22	2018-04-20
US8337886	No	2012-12-25	2018-04-20
US8865688	No	2014-10-21	2030-05-01
US8496965	No	2013-07-30	2018-04-20
US8940328	No	2015-01-27	2018-04-20
US8956647	No	2015-02-17	2018-04-20
US6649180	No	2003-11-18	2020-04-13

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	283 °C	PhysProp
water solubility	0.84 g/L at 20°C	Not Available
logP	1.2	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	12.2 mg/mL	ALOGPS
logP	0.75	ALOGPS
logP	-0.29	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	5.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40 m³·mol^-1	ChemAxon
Polarizability	14.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9471
Blood Brain Barrier	-	0.6168
Caco-2 permeable	-	0.8829
P-glycoprotein substrate	Non-substrate	0.8186
P-glycoprotein inhibitor I	Non-inhibitor	0.985
P-glycoprotein inhibitor II	Non-inhibitor	0.9912
Renal organic cation transporter	Non-inhibitor	0.9314
CYP450 2C9 substrate	Non-substrate	0.8284
CYP450 2D6 substrate	Non-substrate	0.8331
CYP450 3A4 substrate	Non-substrate	0.7636
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.8712
CYP450 2D6 inhibitor	Non-inhibitor	0.9744
CYP450 2C19 inhibitor	Inhibitor	0.6752
CYP450 3A4 inhibitor	Non-inhibitor	0.6628
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9023
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.7922
Biodegradation	Ready biodegradable	0.6197
Rat acute toxicity	1.7065 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9759
hERG inhibition (predictor II)	Non-inhibitor	0.9715

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0f79-0900000000-db75ae2d436dd6156c91

Targets

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Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	A27471

Details1. Prostaglandin G/H synthase 2

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

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]
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]
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]
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]
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]

Details2. Prostaglandin G/H synthase 1

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

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

Details3. Arachidonate 5-lipoxygenase

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

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]
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]
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]

Details4. Peroxisome proliferator-activated receptor gamma

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

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]
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]
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]
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]

Details5. Inhibitor of nuclear factor kappa-B kinase subunit alpha

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

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]
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]
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]

Details6. Inhibitor of nuclear factor kappa-B kinase subunit beta

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

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]
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]
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]

Details7. Myeloperoxidase

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

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]

Enzymes

Details1. Arylamine N-acetyltransferase 1

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

Mesalazine FDA Label [File]

Drug created at June 13, 2005 13:24 / Updated at September 29, 2022 07:52

Mesalazine

Identification

Structure for Mesalazine (DB00244)

Pharmacology

Interactions

Products

Categories

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Clinical Trials

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Properties

Spectra

Targets

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Enzymes

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