Mesalazine
Identification
- Name
- Mesalazine
- Accession Number
- DB00244
- Description
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
Structure for Mesalazine (DB00244)
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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 inhibitorHumans AProstaglandin G/H synthase 1 inhibitorHumans AArachidonate 5-lipoxygenase inhibitorHumans APeroxisome proliferator-activated receptor gamma agonistHumans UInhibitor of nuclear factor kappa-B kinase subunit alpha inhibitorHumans UInhibitor of nuclear factor kappa-B kinase subunit beta inhibitorHumans UMyeloperoxidase Not Available Humans UArylamine N-acetyltransferase Not Available Mycobacterium 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 6. In contrast, when mesalamine is administered orally as an unformulated 1-g aqueous suspension, mesalazine is approximately 80% absorbed 6.
- 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 6.
- 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
Learn about our commercial Adverse Effects data.
Learn More- 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.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAbacavir 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 Acemetacin is combined with Mesalazine. 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. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Images
- International/Other Brands
- Asacolitin / Claversal / Fisalamine / Iialda / Lixacol
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional Data5-asa Tablet, delayed release Oral Sanis Health Inc 2010-11-02 2012-08-03 Canada 
Apriso Capsule, extended release 375 mg/1 Oral Physicians Total Care, Inc. 2010-08-18 Not applicable US 
Apriso Capsule, extended release 375 mg/1 Oral Salix Pharmaceuticals, Inc. 2008-10-31 Not applicable US 
Apriso Capsule, extended release 375 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 2008-10-31 Not applicable US Asacol Tablet, delayed release 400 mg/1 Oral Allergan 1992-04-01 2015-06-30 US Asacol Tablet, delayed release 400 mg/1 Oral Amerincan Health Packaging 2012-01-23 2012-02-29 US Asacol Tablet, delayed release 400 mg Oral Allergan 1993-12-31 2020-07-17 Canada Asacol Tablet, delayed release 400 mg/1 Oral Cardinal Health 1992-04-01 2015-05-31 US Asacol Tablet, delayed release 400 mg/1 Oral REMEDYREPACK INC. 2016-10-06 2016-10-06 US Asacol Tablet, delayed release 400 mg/1 Oral State of Florida DOH Central Pharmacy 2013-01-01 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataMesalamine 4 g/60mL Rectal; Topical Perrigo New York Inc 2009-09-01 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral Cadila Healthcare Limited 2018-08-02 Not applicable US Mesalamine Tablet, delayed release 1.2 g/1 Oral American Health Packaging 2018-09-01 Not applicable US Mesalamine Capsule, delayed release 400 mg/1 Oral Greenstone LLC 2019-05-10 Not applicable US Mesalamine Capsule, extended release 0.375 g/1 Oral Mylan Pharmaceuticals Inc. 2019-11-26 Not applicable US Mesalamine Suppository 1000 mg/1 Rectal Mylan Pharmaceuticals Inc. 2018-12-17 Not applicable US Mesalamine Suppository 1000 mg/1 Rectal Cadila Healthcare Limited 2020-02-14 Not applicable US Mesalamine Enema 4 g/60mL Rectal Perrigo New York Inc 2007-10-11 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral Amerincan Health Packaging 2016-11-18 2019-02-28 US Mesalamine Tablet, delayed release 800 mg/1 Oral Major Pharmaceuticals 2018-08-02 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- A07EC02 — Mesalazine
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Aminosalicylate
- Aminosalicylic Acids
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Benzene Derivatives
- Hydroxybenzoates
- Intestinal Antiinflammatory Agents
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Phenols
- Salicylates
- 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)
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. [PubMed:24369317]
- 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. [PubMed:24005861]
- Electronic Medicines Compendium: Asacol (mesalazine) 400mg MR Tablets Monograph [Link]
- Electronic Medicines Compendium: Pentasa (Mesalazine) Sachet 2g Monograph [Link]
- NIH Toxnet: Mesalazine Profile [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
- 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
- AHFS Codes
- 56:36.00 — Anti-inflammatory Agents
- 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 3 4 Recruiting Treatment Ulcerative Colitis 1 4 Terminated Treatment Crohn's Disease (CD) 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 1600 MG Tablet, delayed release Oral 400 MG Tablet, delayed release Oral 800 MG Tablet, delayed release Oral 800 mg/1 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 Suppository Rectal 1000 mg/1 Suppository Rectal 250 MG Suspension Rectal 4 G/60G Tablet, film coated Oral 500 mg Tablet, delayed release Oral 500 MG Suppository Rectal 500 MG Granule, delayed release Oral 1.5 G Aerosol, foam Rectal 1 G Capsule, delayed release Oral 400 mg/1 Tablet, delayed release Oral 1.2 g/1 Solution Rectal 2 G Solution Rectal 4 G Tablet, coated Oral 500 MG Granule, delayed release Oral 1500 mg Granule, delayed release Oral 3000 mg Capsule, extended release Oral 0.375 g/1 Powder Not applicable 1 g/1g Suspension Rectal 4 g/60mL Aerosol, foam Rectal Capsule Oral 400 MG Gel Rectal 2 G/60ML Gel Rectal 4 G/60ML Gel Rectal 10 % Suspension Rectal 2 G Tablet, extended release Oral 1200 MG Tablet, extended release Oral Suspension Rectal 7 g Suspension Rectal 6667 mg Tablet, delayed release Oral 1200 MG Tablet, extended release Oral 1.2 g Tablet Oral 1200 mg Kit Rectal Suspension Rectal 4 G/100ML Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 Suspension Rectal 1 g Suspension Rectal 2 G/100ML Tablet Oral 250 MG Suspension Rectal 1 g/100ml Granule, delayed release Oral 1 g Tablet, extended release Oral 1 g Suppository Rectal 1.000 MG Suppository Rectal 1000 MG Tablet, extended release Oral 1000 MG Suspension Rectal 1000 MG Suspension Rectal Tablet Oral 500 mg Tablet, extended release Oral 500 MG Enema; liquid Rectal Suspension Rectal 1 g/100 ml Tablet Oral 1 g Granule Oral 1 g Granule Oral 2 g Granule Oral 4 g Granule, delayed release Oral 1000 MG Granule, delayed release Oral Granule, delayed release Oral 4 G Granule, delayed release Oral 2 G Granule Oral 2000 mg Enema Rectal 4 g/60mL Enema Rectal Granule, delayed release Oral 1.5 g/2.79g Suppository Rectal Emulsion Rectal 1 g Granule Oral 3000 mg Suppository Rectal 1 G Granule Oral 1.5 g Tablet, delayed release Oral 1 G Tablet, delayed release Oral 250 MG Suspension Rectal 2 G/30ML Granule Oral 3 g Tablet, delayed release Oral Granule, delayed release Oral 3 G Granule, delayed release Oral 500 MG Granule Oral 1500 mg Granule Oral 1000 mg Suspension Rectal 4 g Granule 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) Region Unlock Additional DataUS5541170 No 1996-07-30 2013-07-30 US CA2444814 No 2009-06-09 2021-10-24 Canada CA2111697 No 2002-08-20 2012-06-16 Canada US7645801 No 2010-01-12 2027-07-24 US US6773720 No 2004-08-10 2020-06-08 US US8436051 No 2013-05-07 2028-06-06 US US8217083 No 2012-07-10 2028-06-06 US US6893662 No 2005-05-17 2021-11-15 US US8580302 No 2013-11-12 2021-11-15 US US9089492 No 2015-07-28 2021-11-15 US US8911778 No 2014-12-16 2018-04-20 US US6551620 No 2003-04-22 2018-04-20 US US8337886 No 2012-12-25 2018-04-20 US US8865688 No 2014-10-21 2030-05-01 US US8496965 No 2013-07-30 2018-04-20 US US8940328 No 2015-01-27 2018-04-20 US US8956647 No 2015-02-17 2018-04-20 US US6649180 No 2003-11-18 2020-04-13 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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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
Spectra
- Mass Spec (NIST)
- Download (8.48 KB)
- 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
- 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. [PubMed:14742690]
- 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]
- 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]
- 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]
- 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
- 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. [PubMed:12950415]
- 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
- 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. [PubMed:2882965]
- 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]
- 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
- 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. [PubMed:15824083]
- 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]
- 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]
- 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
- 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. [PubMed:11151876]
- 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]
- 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
- 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. [PubMed:11151876]
- 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]
- 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
- 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. [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
- 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]
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
- Mesalazine FDA Label [File]
Drug created on June 13, 2005 07:24 / Updated on October 31, 2020 10:29
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