Mesalazine

Identification

Summary

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

Brand Names

Apriso, Asacol, Canasa, Delzicol, Lialda, Mezavant, Pentasa, Rowasa, Salofalk, Zaldyon

Generic Name

Mesalazine

DrugBank Accession Number

DB00244

Background

An anti-inflammatory agent, structurally related to the salicylates and non-steroidal anti-inflammatory drugs like acetylsalicylic acid, which is active in inflammatory bowel disease ². 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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Mesalazine (DB00244)

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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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Associated Conditions

• Crohn's Disease Relapse
• Crohn's Ileocolitis
• Mild to Moderate Ulcerative Colitis
• Proctitis
• Proctitis, Ulcerative
• Proctosigmoiditis
• Ulcerative Colitis Acute
• Ulcerative Colitis in Remission
• Mild Ulcerative Colitis
• Mild to moderate distal ulcerative colitis
• Moderate Ulcerative colitis

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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	inhibitor	Humans
AProstaglandin G/H synthase 1	inhibitor	Humans
AArachidonate 5-lipoxygenase	inhibitor	Humans
APeroxisome proliferator-activated receptor gamma	agonist	Humans
UInhibitor of nuclear factor kappa-B kinase subunit alpha	inhibitor	Humans
UInhibitor of nuclear factor kappa-B kinase subunit beta	inhibitor	Humans
UNitric oxide synthase, inducible	inhibitor	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.²⁶ In contrast, when mesalamine is administered orally as an unformulated 1-g aqueous suspension, mesalazine is approximately 80% absorbed.²⁶

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

Hover over products below to view reaction partners

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

Route of elimination

Elimination of mesalazine is mainly via the renal route following metabolism to N-acetyl-5-aminosalicylic acid (acetylation) 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.²⁶

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 t_{1/2 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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Toxicity

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

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Mesalazine may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding 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.
Acemetacin	The risk or severity of nephrotoxicity can be increased when Mesalazine is combined with Acemetacin.
Acenocoumarol	Mesalazine may increase the anticoagulant activities of Acenocoumarol.
Acetaminophen	The risk or severity of adverse effects can be increased when Acetaminophen is combined with Mesalazine.
Acetazolamide	The risk or severity of adverse effects can be increased when Mesalazine is combined with Acetazolamide.
Acetohexamide	Mesalazine may increase the hypoglycemic activities of Acetohexamide.

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Food Interactions

• Take with or without food. The absorption is unaffected by food.

Products

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Product Images

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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
Apriso	Capsule, extended release	375 mg/1	Oral	Physicians Total Care, Inc.	2010-08-18	Not applicable
Apriso	Capsule, extended release	375 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2008-10-31	Not applicable
Apriso	Capsule, extended release	375 mg/1	Oral	Salix Pharmaceuticals, Inc.	2008-10-31	Not applicable
Asacol	Tablet, delayed release	400 mg/1	Oral	Amerincan Health Packaging	2012-01-23	2012-02-29
Asacol	Tablet, delayed release	400 mg/1	Oral	Allergan, Inc.	1992-04-01	2015-06-30
Asacol	Tablet, delayed release	400 mg	Oral	Allergan	1993-12-31	2020-07-17
Asacol	Tablet, delayed release	400 mg/1	Oral	REMEDYREPACK INC.	2016-10-06	2016-10-06
Asacol	Tablet, delayed release	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2013-01-01	Not applicable
Asacol	Tablet, delayed release	400 mg/1	Oral	Remedy Repack	2011-03-09	2016-11-28

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Mesalamine	Suppository	1000 mg/1	Rectal	Rising Pharmaceuticals, Inc.	2019-06-05	Not applicable
Mesalamine	Tablet, delayed release	1.2 g/1	Oral	Mylan Pharmaceuticals Inc.	2018-12-14	Not applicable
Mesalamine	Capsule, delayed release	400 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2019-05-09	Not applicable
Mesalamine	Capsule, extended release	500 mg/1	Oral	Sun Pharmaceutical Industries Inc.	2022-05-13	Not applicable
Mesalamine	Suppository	1000 mg/1	Rectal	Greenstone LLC	2018-12-07	Not applicable
Mesalamine	Suppository	1000 mg/1	Rectal	Sandoz Inc	2019-11-01	2023-08-31
Mesalamine	Suppository	1000 mg/1	Rectal	Actavis Pharma, Inc.	2021-04-23	Not applicable
Mesalamine	Suppository	1000 mg/1	Rectal	Amneal Pharmaceuticals NY LLC	2020-01-08	2023-05-01
Mesalamine	Capsule, extended release	375 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2021-01-05	Not applicable
Mesalamine	Tablet, delayed release	800 mg/1	Oral	Amerincan Health Packaging	2016-11-18	2019-02-28

Categories

ATC Codes

A07EC02 — Mesalazine

• A07EC — Aminosalicylic acid and similar agents
• A07E — INTESTINAL ANTIINFLAMMATORY AGENTS
• A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
• A — ALIMENTARY TRACT AND METABOLISM

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 / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives

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 / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxybenzoic acid / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / P-aminophenol / Phenol / Primary amine / Salicylic acid / Salicylic acid or derivatives / Vinylogous acid

show 17 more

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid, phenols, aromatic amine, amino acid, monohydroxybenzoic acid (CHEBI:6775)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

4Q81I59GXC

CAS number

89-57-6

InChI Key

KBOPZPXVLCULAV-UHFFFAOYSA-N

InChI

InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

IUPAC Name

5-amino-2-hydroxybenzoic acid

SMILES

NC1=CC(C(O)=O)=C(O)C=C1

References

Synthesis Reference

Thomas M. Parkinson, Joseph P. Brown, Robert E. Wingard, Jr., "Pharmaceutical preparations containing a polymeric agent for releasing 5-aminosalicylic acid or its salts into the gastrointestinal tract." U.S. Patent US4298595, issued January, 1975.

US4298595

General References

1. Mayberry J: The history of 5-ASA compounds and their use in ulcerative colitis--trailblazing discoveries in gastroenterology. J Gastrointestin Liver Dis. 2013 Dec;22(4):375-7. [Article]
2. Stolfi C, De Simone V, Pallone F, Monteleone G: Mechanisms of action of non-steroidal anti-inflammatory drugs (NSAIDs) and mesalazine in the chemoprevention of colorectal cancer. Int J Mol Sci. 2013 Sep 3;14(9):17972-85. doi: 10.3390/ijms140917972. [Article]
3. 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]
4. 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]
5. 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]
6. 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]
7. 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]
8. 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]
9. 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]
10. 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]
11. 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]
12. Electronic Medicines Compendium: Asacol (mesalazine) 400mg MR Tablets Monograph [Link]
13. Electronic Medicines Compendium: Pentasa (Mesalazine) Sachet 2g Monograph [Link]
14. FDA Approved Drug Products: Asacol HD (mesalamine) delayed-release tablets for oral use [Link]
15. FDA Approved Drug Products: Delzicol (mesalamine) delayed-release capsules for oral use [Link]
16. FDA Approved Drug Products: Canasa (mesalamine) suppositories for rectal use [Link]
17. FDA Approved Drug Products: APRISO® (mesalamine) extended-release capsules [Link]
18. Electronic Medicines Compendium: Mezavant XL 1200mg, gastro-resistant, prolonged release tablets [Link]
19. Clinical Pharmacology Review : Asacol HD [Link]
20. Mesalazine MSDS Pharmacopoeia [Link]
21. Mesalazine MSDS Allergan [Link]
22. Mesalazine MSDS USP [Link]
23. FDA Approved Drug Products: LIALDA (mesalamine) delayed-release tablets, for oral use [Link]
24. FDA Approved Drug Products: ROWASA (mesalamine) Rectal Suspension Enema [Link]
25. Product Monograph: SALOFALK (mesalamine) delayed release tablets, for oral use [Link]
26. Pentasa (Mesalazine) FDA Label [File]

External Links

Human Metabolome Database

HMDB0014389

KEGG Drug

D00377

PubChem Compound

4075

PubChem Substance

46509142

ChemSpider

3933

BindingDB

60918

RxNav

52582

ChEBI

6775

ChEMBL

CHEMBL704

ZINC

ZINC000000001688

Therapeutic Targets Database

DAP000729

PharmGKB

PA450384

Guide to Pharmacology

GtP Drug Page

RxList

RxList Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Mesalazine

FDA label

Download (1.61 MB)

MSDS

Download (67.7 KB)

Clinical Trials

Clinical Trials

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

Pharmacoeconomics

Manufacturers

• Salix pharmaceuticals inc
• Shire development inc
• Perrigo israel pharmaceuticals ltd
• Teva pharmaceuticals usa inc
• Alaven pharmaceutical llc
• Axcan pharma us inc
• Warner chilcott pharmaceuticals inc

Packagers

• Alaven Pharmaceutical
• Amerisource Health Services Corp.
• Anip Acquisition Co.
• Atlantic Biologicals Corporation
• Axcan Pharma Inc.
• Cardinal Health
• Comprehensive Consultant Services Inc.
• Cosmo SPA
• Dept Health Central Pharmacy
• Diversified Healthcare Services Inc.
• Ferring Pharmaceuticals Inc.
• Franklin Pharmaceutical LLC
• Gavis Pharmaceuticals LLC
• Heartland Repack Services LLC
• Infar SA
• Letco Medical Inc.
• Norwich Pharmaceuticals Inc.
• Paddock Labs
• PD-Rx Pharmaceuticals Inc.
• Perrigo Co.
• Physicians Total Care Inc.
• Prasco Labs
• Prepak Systems Inc.
• Resource Optimization and Innovation LLC
• Salix Pharmaceuticals
• Sanofi-Aventis Inc.
• Shire Inc.
• Solvay Pharmaceuticals
• Teva Pharmaceutical Industries Ltd.
• Vangard Labs Inc.
• Warner Chilcott Co. Inc.
• WC Pharmaceuticals
• Wellspring Pharmaceutical

Dosage Forms

Form	Route	Strength
Capsule, extended release	Oral	375 mg/1
Capsule, delayed release	Oral	400 MG
Granule, for suspension	Rectal	2 G
Suspension	Rectal	2 G/50ML
Suspension	Rectal	4 G/50ML
Tablet	Oral	400 mg/1
Tablet, delayed release	Oral	400 mg/1
Tablet, delayed release	Oral
Tablet, delayed release	Oral	800 mg/1
Tablet, coated	Oral	400 mg
Tablet, coated	Oral	800 mg
Aerosol, foam	Rectal	2 G
Aerosol, foam	Rectal	4 G
Enema	Rectal	2 G
Enema	Rectal	4 G
Gel	Rectal	500 MG
Granule, for suspension	Rectal	1.5 G
Suppository	Rectal	400 MG
Tablet	Oral	400 MG
Tablet	Oral	800 MG
Suspension	Rectal
Tablet, delayed release	Oral	1000 mg
Suppository	Rectal	1000 mg/1
Suppository	Rectal	0.5 g
Suspension	Rectal	4 g
Suspension	Rectal	2 g
Suspension	Rectal	4 G/60G
Tablet, film coated	Oral	500 mg
Capsule, delayed release	Oral	400 mg/1
Tablet, coated	Oral
Tablet, delayed release	Oral	1.2 g/1
Suspension	Rectal	6.67 g
Tablet, coated	Oral	500 mg
Tablet, delayed release	Oral	400 mg
Solution	Rectal	2 G
Solution	Rectal	4 G
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
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
Tablet, extended 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	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	Oral	500 mg/1sachet
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
CA2444814	No	2009-06-09	2021-10-24
CA2111697	No	2002-08-20	2012-06-16
US7645801	No	2010-01-12	2027-07-24
US6773720	No	2004-08-10	2020-06-08
US8436051	No	2013-05-07	2028-06-06
US8217083	No	2012-07-10	2028-06-06
US6893662	No	2005-05-17	2021-11-15
US8580302	No	2013-11-12	2021-11-15
US9089492	No	2015-07-28	2021-11-15
US8911778	No	2014-12-16	2018-04-20
US6551620	No	2003-04-22	2018-04-20
US8337886	No	2012-12-25	2018-04-20
US8865688	No	2014-10-21	2030-05-01
US8496965	No	2013-07-30	2018-04-20
US8940328	No	2015-01-27	2018-04-20
US8956647	No	2015-02-17	2018-04-20
US6649180	No	2003-11-18	2020-04-13

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	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

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

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

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Binding Properties

×

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

Details

Binding Properties1. Prostaglandin G/H synthase 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Prostaglandin-endoperoxide synthase activity

Specific Function

Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...

Gene Name

PTGS2

Uniprot ID

P35354

Uniprot Name

Prostaglandin G/H synthase 2

Molecular Weight

68995.625 Da

References

1. Mifflin RC, Saada JI, Di Mari JF, Valentich JD, Adegboyega PA, Powell DW: Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8. [Article]
2. Generini S, Fiori G, Matucci Cerinic M: Therapy of spondylarthropathy in inflammatory bowel disease. Clin Exp Rheumatol. 2002 Nov-Dec;20(6 Suppl 28):S88-94. [Article]
3. Distrutti E, Sediari L, Mencarelli A, Renga B, Orlandi S, Russo G, Caliendo G, Santagada V, Cirino G, Wallace JL, Fiorucci S: 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3yl)-phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol Exp Ther. 2006 Oct;319(1):447-58. Epub 2006 Jul 19. [Article]
4. Cipolla G, Crema F, Sacco S, Moro E, de Ponti F, Frigo G: Nonsteroidal anti-inflammatory drugs and inflammatory bowel disease: current perspectives. Pharmacol Res. 2002 Jul;46(1):1-6. [Article]
5. Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [Article]

Details2. Prostaglandin G/H synthase 1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Prostaglandin-endoperoxide synthase activity

Specific Function

Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...

Gene Name

PTGS1

Uniprot ID

P23219

Uniprot Name

Prostaglandin G/H synthase 1

Molecular Weight

68685.82 Da

References

1. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Details3. Arachidonate 5-lipoxygenase

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Iron ion binding

Specific Function

Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.

Gene Name

ALOX5

Uniprot ID

P09917

Uniprot Name

Arachidonate 5-lipoxygenase

Molecular Weight

77982.595 Da

References

1. Nielsen OH, Bukhave K, Elmgreen J, Ahnfelt-Ronne I: Inhibition of 5-lipoxygenase pathway of arachidonic acid metabolism in human neutrophils by sulfasalazine and 5-aminosalicylic acid. Dig Dis Sci. 1987 Jun;32(6):577-82. [Article]
2. Allgayer H, Eisenburg J, Paumgartner G: Soybean lipoxygenase inhibition: studies with the sulphasalazine metabolites N-acetylaminosalicylic acid, 5-aminosalicylic acid and sulphapyridine. Eur J Clin Pharmacol. 1984;26(4):449-51. [Article]
3. Sircar JC, Schwender CF, Carethers ME: Inhibition of soybean lipoxygenase by sulfasalazine and 5-aminosalicylic acid: a possible mode of action in ulcerative colitis. Biochem Pharmacol. 1983 Jan 1;32(1):170-2. [Article]

Details4. Peroxisome proliferator-activated receptor gamma

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Zinc ion binding

Specific Function

Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...

Gene Name

PPARG

Uniprot ID

P37231

Uniprot Name

Peroxisome proliferator-activated receptor gamma

Molecular Weight

57619.58 Da

References

1. Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, Chavatte P, Farce A, Bulois P, Cortot A, Colombel JF, Desreumaux P: Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 2005 Apr 18;201(8):1205-15. Epub 2005 Apr 11. [Article]
2. Schwab M, Reynders V, Loitsch S, Shastri YM, Steinhilber D, Schroder O, Stein J: PPARgamma is involved in mesalazine-mediated induction of apoptosis and inhibition of cell growth in colon cancer cells. Carcinogenesis. 2008 Jul;29(7):1407-14. doi: 10.1093/carcin/bgn118. Epub 2008 Jun 9. [Article]
3. Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [Article]
4. Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [Article]

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

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Scaffold protein binding

Specific Function

Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...

Gene Name

CHUK

Uniprot ID

O15111

Uniprot Name

Inhibitor of nuclear factor kappa-B kinase subunit alpha

Molecular Weight

84638.88 Da

References

1. Bantel H, Berg C, Vieth M, Stolte M, Kruis W, Schulze-Osthoff K: Mesalazine inhibits activation of transcription factor NF-kappaB in inflamed mucosa of patients with ulcerative colitis. Am J Gastroenterol. 2000 Dec;95(12):3452-7. [Article]
2. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
3. Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [Article]

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

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Scaffold protein binding

Specific Function

Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...

Gene Name

IKBKB

Uniprot ID

O14920

Uniprot Name

Inhibitor of nuclear factor kappa-B kinase subunit beta

Molecular Weight

86563.245 Da

References

1. Bantel H, Berg C, Vieth M, Stolte M, Kruis W, Schulze-Osthoff K: Mesalazine inhibits activation of transcription factor NF-kappaB in inflamed mucosa of patients with ulcerative colitis. Am J Gastroenterol. 2000 Dec;95(12):3452-7. [Article]
2. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [Article]
3. Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [Article]

Details7. Nitric oxide synthase, inducible

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

1. Nandi J, Saud B, Zinkievich JM, Palma DT, Levine RA: 5-aminosalicylic acid improves indomethacin-induced enteropathy by inhibiting iNOS transcription in rats. Dig Dis Sci. 2008 Jan;53(1):123-32. Epub 2007 May 15. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 02, 2023 04:04