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
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.
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- Contraindications & Blackbox Warnings
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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 - 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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- 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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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 Integrate drug-drug
interactions in your softwareAbacavir 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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- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 5-asa Tablet, delayed release 400 mg Oral Sanis Health Inc 2010-11-02 2012-08-03 Canada 
Apriso Capsule, extended release 375 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 2008-10-31 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 Physicians Total Care, Inc. 2010-08-18 Not applicable US 
Asacol Tablet, delayed release 400 mg/1 Oral Remedy Repack 2011-03-09 2016-11-28 US Asacol Tablet, delayed release 400 mg/1 Oral Physicians Total Care, Inc. 2002-05-10 2011-06-30 US 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 State of Florida DOH Central Pharmacy 2009-07-01 Not applicable US 
Asacol Tablet, delayed release 400 mg/1 Oral Cardinal Health 1992-04-01 2012-12-31 US 
Asacol Tablet, delayed release 400 mg/1 Oral Warner Chilcott 1992-04-01 2011-11-17 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mesalamine Capsule, delayed release 400 mg/1 Oral REMEDYREPACK INC. 2021-10-13 Not applicable US Mesalamine Enema 4 g/60mL Rectal ANI Pharmaceuticals, Inc. 2016-05-13 Not applicable US Mesalamine Suppository 1000 mg/1 Rectal Zydus Pharmaceuticals (USA) Inc. 2020-02-14 Not applicable US Mesalamine Capsule, delayed release 400 mg/1 Oral American Health Packaging 2021-04-01 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2016-08-01 Not applicable US Mesalamine Suppository 1000 mg/1 Rectal Northstar Rx Llc. 2021-08-25 Not applicable US Mesalamine Tablet, delayed release 1.2 g/1 Oral Northstar Rx Llc. 2018-06-25 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral A-S Medication Solutions 2016-08-01 Not applicable US Mesalamine Enema; Kit 4 g/60mL Rectal Padagis Israel Pharmaceuticals Ltd 2009-09-01 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2016-08-01 Not applicable US
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)
- 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
- 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
- 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 / 100 mL Suspension Rectal 1 G/100ML 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) Region US5541170 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
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. [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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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 August 12, 2022 17:06