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. 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 treatment of mildly to moderately active ulcerative colitis in adults and patients 5 years or older.16,15. Mesalazine is also indicated for the maintenance of remission of ulcerative colitis in adults and maintenance of remission of Crohn's ileocolitis.17,12
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Crohn's disease relapse •••••••••••• ••••••• ••••••• ••••••• Management of Crohn's ileocolitis •••••••••••• ••••••• ••••••• ••••••• Management of Mild to moderate ulcerative colitis •••••••••••• •••••••• ••• ••••••••••• •••••••• ••••••• Management of Mild to moderate ulcerative colitis •••••••••••• ••••••• ••••••• ••••••• Management of Proctitis •••••••••••• ••••• •••••• •••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Mesalazine is one of the two components of sulphasalazine, the other being sulphapyridine. It is the latter responsible for most of the side effects associated with sulphasalazine therapy, while mesalazine is known to be the active moiety in the treatment of ulcerative colitis 12.
Mesalazine is thought to dampen the inflammatory process through its ability to inhibit prostaglandin synthesis, interfere with leukotriene synthesis, and consequent leukocyte migration as well as act as a potent scavenger of free radicals.25 Regardless of the mode of action, mesalazine appears to be active mainly topically rather than systemically.25
Intraperitoneally administered mesalazine at 30 and 340 mg/kg daily had similar efficacy in attenuating colitis as prednisolone 4 to 550 mg/kg daily given intraperitoneally or sulphasalazine 0.34 to 5 mg/kg given orally in immune complex-induced colitis mice.11 Mesalazine at 5 mmol/L and sulphasalazine 1.5 mmol/L also reversed the increase in water and chloride secretion and decrease the sodium in dinitrochlorbenzene-induced colitis guinea pig.11
- 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.14 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.14
Furthermore, mesalazine also has the potential to inhibit the activation of Nuclear Factor kappa B (NFkB) and consequently the production of key pro-inflammatory cytokines.3,4,5 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, and that mesalazine produces pharmacodynamic effects through direct activation of PPAR gamma receptors in the colonic/rectal epithelium.9,6,7,8 Other research also showed the potential involvement of inducible NO synthase (iNOS) and that mesalazine can inhibit this enzyme to amiliorate the enteropathy in inflammatory bowel diseases.25
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.13
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 UNitric oxide synthase, inducible inhibitorHumans - 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.27 In contrast, when mesalamine is administered orally as an unformulated 1-g aqueous suspension, mesalazine is approximately 80% absorbed.27
- Volume of distribution
For the extended-release formulation, mesalazine has a Vd of 18 L, confirming minimal extravascular penetration of systemically available drug.18 For the delayed-release formulation, the apparent volume of distribution was estimated to be 4.8 L.19
- Protein binding
In an in vitro study, at 2.5 mcg/mL, mesalamine and N-Ac-5-ASA are 43±6% and 78±1% bound, respectively, to plasma proteins. Protein binding of N-Ac-5-ASA does not appear to be concentration dependent at concentrations ranging from 1 to 10 mcg/mL.17
- Metabolism
Mesalazine is metabolized both pre-systemically by the intestinal mucosa and systemically in the liver to N-acetyl-5-aminosalicylic acid (N-Ac-5-ASA) principally by NAT-1. Some acetylation also occurs through the action of colonic bacteria.13,17
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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) 23. However, there is also limited excretion of the parent mesalazine drug in the urine.23
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.23
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.27
In patients with ulcerative proctitis treated with mesalamine 500 mg as a rectal suppository every 8 hours for 6 days, 12% or less of the dose was eliminated in urine as unchanged 5-ASA and 8% to 77% was eliminated as N-acetyl-5-ASA following the initial dose. At steady state, 11% or less of the dose was eliminated in the urine as unchanged 5-ASA and 3% to 35% was eliminated as N-acetyl-5-ASA.16
- Half-life
For the delayed-release formulation, after intravenous administration, the elimination half-life of mesalamine is reported to be approximately 40 minutes. After oral dosing, the median terminal half life values for mesalamine are usually about 25 hours, but are variable, ranging from 1.5 to 296 hours. There is a large inter-subject and intra-subject variability in the plasma concentrations of mesalamine and N-acetyl-5-aminosalicylic acid and in their terminal half-lives following the administration of mesalazine.15 For the extended-release formulation, following single and multiple doses of mesalazine, the mean half-lives were 9 to 10 hours for 5-ASA, and 12 to 14 hours for N-Ac-5-ASA.17
The mean elimination half-life was 5 hours (CV=73%) for 5-ASA and 5 hours (CV=63%) for N-acetyl-5-ASA in patients taking 500 mg mesalazine as a rectal suppository every 8 hours for 6 days.16 For the rectal enema suspension formulation, the elimination half-life was 0.5 to 1.5 hours for 5-ASA and 5 to 10 hours for N-acetyl-5-ASA.24
- 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 were 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.23
- Adverse Effects
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Mesalazine caused no increase in the incidence of neoplastic lesions over controls in a two-year study of Wistar rats fed up to 320 mg/kg/day of mesalazine admixed with diet (about 1.7 times the recommended human intra-rectal dose of CANASA, based on body surface area). Mesalazine was not mutagenic in the Ames test, the mouse lymphoma cell (TK+/-) forward mutation test, or the mouse micronucleus test. No effects on fertility or reproductive performance of the male and female rats were observed at oral mesalamine doses up to 320 mg/kg/day (about 1.7 times the recommended human intra-rectal dose of mesalazine, based on body surface area).16
Mesalazine is an aminosalicylate, and symptoms of salicylate toxicity include nausea, vomiting and abdominal pain, tachypnea, hyperpnea, tinnitus, and neurologic symptoms (headache, dizziness, confusion, seizures). Severe salicylate intoxication may lead to electrolyte and blood pH imbalance and potentially to other organ involvement (e.g., renal and liver). There is no specific antidote for mesalamine overdose; however, conventional therapy for salicylate toxicity may be beneficial in the event of acute overdosage and may include gastrointestinal tract decontamination to prevent further absorption. Correct fluid and electrolyte imbalance by the administration of appropriate intravenous therapy and maintain adequate renal function.14
Mesalazine is known to be substantially excreted by the kidney, and the risk of adverse reactions may be greater in patients with impaired renal function. Evaluate renal function in all patients prior to initiation and periodically while on Asacol HD therapy. Monitor patients with known renal impairment or a history of renal disease or taking nephrotoxic drugs for decreased renal function and mesalamine-related adverse reactions.14
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 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 risk or severity of nephrotoxicity can be increased when Mesalazine is combined with Aceclofenac. - Food Interactions
- 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 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 Apriso Capsule, extended release 375 mg/1 Oral Physicians Total Care, Inc. 2010-08-18 Not applicable US 
Asacol Tablet 400 mg/1 Oral Remedy Repack 2010-08-10 2012-02-16 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mesalamine Suppository 1000 mg/1 Rectal Zydus Lifesciences Limited 2020-02-14 Not applicable US Mesalamine Capsule, extended release 0.375 g/1 Oral American Health Packaging 2022-06-20 Not applicable US Mesalamine Enema; Kit 4 g/60mL Rectal bryant ranch prepack 2018-08-02 Not applicable US Mesalamine Tablet, delayed release 1.2 g/1 Oral Zydus Pharmaceuticals USA Inc. 2017-06-19 Not applicable US Mesalamine Tablet, delayed release 800 mg/1 Oral American Health Packaging 2019-04-17 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
- Benzene Derivatives
- Hydroxybenzoates
- Intestinal Antiinflammatory Agents
- Nephrotoxic agents
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- OATP2B1/SLCO2B1 substrates
- 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]
- 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]
- 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]
- 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]
- 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]
- Brogden RN, Sorkin EM: Mesalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in chronic inflammatory bowel disease. Drugs. 1989 Oct;38(4):500-23. doi: 10.2165/00003495-198938040-00003. [Article]
- Electronic Medicines Compendium: Asacol (mesalazine) 400mg MR Tablets Monograph [Link]
- Electronic Medicines Compendium: Pentasa (Mesalazine) Sachet 2g Monograph [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]
- FDA Approved Drug Products: APRISO® (mesalamine) extended-release capsules [Link]
- Electronic Medicines Compendium: Mezavant XL 1200mg, gastro-resistant, prolonged release tablets [Link]
- Clinical Pharmacology Review : Asacol HD [Link]
- Mesalazine MSDS Pharmacopoeia [Link]
- Mesalazine MSDS Allergan [Link]
- Mesalazine MSDS USP [Link]
- FDA Approved Drug Products: LIALDA (mesalamine) delayed-release tablets, for oral use [Link]
- FDA Approved Drug Products: ROWASA (mesalamine) Rectal Suspension Enema [Link]
- Product Monograph: SALOFALK (mesalamine) delayed release tablets, for oral use [Link]
- FDA Approved Drug Products: Apriso (mesalamine) extended-release capsules for oral 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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
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/100ML 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 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 Gel Rectal 10 % Tablet Oral 1200.000 mg Tablet, delayed release Oral 1000 mg Suppository Rectal 1000 mg/1 Suppository Rectal 0.5 g Suspension Rectal 4 G/60G Tablet, film coated Oral 500 mg Aerosol, foam Rectal 1 G Tablet Oral 250.000 mg Capsule, delayed release Oral 400 mg/1 Tablet Oral 1200.00 mg Tablet, coated Oral Tablet, delayed release Oral 1.2 g/1 Suspension Rectal 6.67 g Tablet, delayed release Oral 400 mg Solution Rectal 2 G Solution Rectal 4 G Granule, delayed release Oral 1000 mg Granule, delayed release Oral 1500 mg Granule, delayed release Oral 3000 mg Granule, delayed release Oral 500 mg 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 Suspension Rectal 2 G Suspension Rectal 4 G Tablet Oral 1200 MG 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 Tablet Oral 500.000 mg Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 Granule Oral 1 G Granule Oral 2.000 g Suppository Rectal Suppository Rectal 1.000 g Suspension Rectal 1 G/100ML Suspension Rectal 1 g / 100 mL Suspension Rectal 2 G/100ML Suspension Rectal 4 g / 100 mL Tablet Oral 1 G Tablet Oral 250 MG Tablet, extended release Oral 1 g Enema Rectal 1 g Enema Rectal 1 g/100ml Tablet, extended release Oral Suppository Rectal 1.000 MG Suspension Rectal 1000 MG Tablet, extended release Oral 50000000 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 Oral 1000 mg Tablet Oral 500 mg Suspension Rectal 0.01 g/ml 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 200000000 mg Capsule Oral Enema Rectal 4 g/60mL Enema Rectal Granule Oral 1000.00 mg Granule Oral 1500 MG Suppository Rectal 250.000 mg Suspension Rectal 2 g / 60 g Suspension Rectal 4 g / 60 g Suspension Rectal 4.0000 g Tablet Oral Emulsion Rectal 1 g Granule Oral 3000 mg Granule Oral 1.5 g Granule, delayed release Oral 1.5 g Granule Oral 1000 mg 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 Suppository Rectal 50000000 mg Tablet, coated Oral 500 mg Granule Oral 500 mg Granule Oral 500 mg/1sachet Suspension Rectal 400000 g Tablet, delayed release Oral 50000000 mg Suspension Rectal 6.667 g Tablet 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) 260-280 °C L44306 water solubility 0.84 g/L at 20°C L44296 - 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 131.8545263 predictedDarkChem Lite v0.1.0 [M-H]- 131.6773263 predictedDarkChem Lite v0.1.0 [M-H]- 132.0126263 predictedDarkChem Lite v0.1.0 [M-H]- 128.3325 predictedDeepCCS 1.0 (2019) [M-H]- 131.8545263 predictedDarkChem Lite v0.1.0 [M-H]- 131.6773263 predictedDarkChem Lite v0.1.0 [M-H]- 132.0126263 predictedDarkChem Lite v0.1.0 [M-H]- 128.3325 predictedDeepCCS 1.0 (2019) [M+H]+ 133.0074263 predictedDarkChem Lite v0.1.0 [M+H]+ 133.2136263 predictedDarkChem Lite v0.1.0 [M+H]+ 132.9304263 predictedDarkChem Lite v0.1.0 [M+H]+ 131.64499 predictedDeepCCS 1.0 (2019) [M+H]+ 133.0074263 predictedDarkChem Lite v0.1.0 [M+H]+ 133.2136263 predictedDarkChem Lite v0.1.0 [M+H]+ 132.9304263 predictedDarkChem Lite v0.1.0 [M+H]+ 131.64499 predictedDeepCCS 1.0 (2019) [M+Na]+ 132.1999263 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.1872263 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.1851263 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.11731 predictedDeepCCS 1.0 (2019) [M+Na]+ 132.1999263 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.1872263 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.1851263 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.11731 predictedDeepCCS 1.0 (2019)
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
- Actions
- Inhibitor
- General Function
- Tetrahydrobiopterin binding
- Specific Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 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
- No
- 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]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Konig J, Glaeser H, Keiser M, Mandery K, Klotz U, Fromm MF: Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. Drug Metab Dispos. 2011 Jun;39(6):1097-102. doi: 10.1124/dmd.110.034991. Epub 2011 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Konig J, Glaeser H, Keiser M, Mandery K, Klotz U, Fromm MF: Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. Drug Metab Dispos. 2011 Jun;39(6):1097-102. doi: 10.1124/dmd.110.034991. Epub 2011 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Konig J, Glaeser H, Keiser M, Mandery K, Klotz U, Fromm MF: Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. Drug Metab Dispos. 2011 Jun;39(6):1097-102. doi: 10.1124/dmd.110.034991. Epub 2011 Mar 23. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55