MESALAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7NO3
Molecular Weight	153.1354
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KBOPZPXVLCULAV-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description

Mesalamine, also known as Mesalazine or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism. Although the mechanism of action of mesalazine is not fully understood, it appears to be topical rather than systemic. 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. Mesalazine is used for the treatment of active ulcerative proctitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nitric oxide synthase, inducible 36	Inhibitor 7464	Colitis, Ulcerative
Intermediate conductance calcium-activated potassium channel protein 4 6	Inhibitor 7464		26.0 µM [EC50]
Cyclooxygenase-1 121	Inhibitor 7464	Colitis, Ulcerative
Arachidonate 5-lipoxygenase 47	Inhibitor 7464	Colitis, Ulcerative
reactive oxygen species biosynthetic process 30	Inhibitor 7464	Colitis, Ulcerative	0.69 µM [IC50]
Peroxisome proliferator-activated receptor gamma 96	Agonist 2354	Colitis, Ulcerative
macrophage chemotaxis 1	Inhibitor 7464	Colitis, Ulcerative	0.24 mM [IC50]
apoptotic process 44	Inhibitor 7464	Colitis, Ulcerative	16.0 µM [IC50]
Cyclooxygenase-2 184	Inhibitor 7464	Colitis, Ulcerative

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colitis, Ulcerative 32	Primary	Nitric oxide synthase, inducible apoptotic process Cyclooxygenase-2 macrophage chemotaxis Cyclooxygenase-1 Peroxisome proliferator-activated receptor gamma Arachidonate 5-lipoxygenase reactive oxygen species biosynthetic process	Approved 7888	PENTASA
Crohn's disease 4			Approved (off-label) 8

PubMed

Title	Date	PubMed
[Early renal failure caused by mesalazine].	2000 Oct	11344635
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
TNF-alpha induced endothelial MAdCAM-1 expression is regulated by exogenous, not endogenous nitric oxide.	2001	11481030
Tolerability of aminosalicylates in inflammatory bowel disease.	2001	11437696
[Hepatotoxicity of medications].	2001 Apr 14	11360729
[The new experimental ulcerative colitis model in rats induced by subserosal injection of acetic acid].	2001 Aug	11530682
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.	2001 Aug	11529938
Mesalazine 4 g daily given as prolonged-release granules twice daily and four times daily is at least as effective as prolonged-release tablets four times daily in patients with ulcerative colitis.	2001 Aug	11515850
Measurement of colonic mucosal concentrations of 5-aminosalicylic acid is useful for estimating its therapeutic efficacy in distal ulcerative colitis: comparison of orally administered mesalamine and sulfasalazine.	2001 Aug	11515848
The expression of IL-12 p40 and its homologue, Epstein-Barr virus-induced gene 3, in inflammatory bowel disease.	2001 Aug	11515847
Inflammatory pseudotumor of the liver as the first manifestation of Crohn's disease.	2001 Aug	11513216
Adult fibrosing colonopathy associated with mesalazine treatment.	2001 Aug	11513205
[Metastatic Crohn's disease in childhood].	2001 Aug	11472671
Glucocorticoids and IL-10, but not 6-MP, 5-ASA or sulfasalazine block endothelial expression of MAdCAM-1: implications for inflammatory bowel disease therapy.	2001 Aug	11472325
Renal tubular injury is present in acute inflammatory bowel disease prior to the introduction of drug therapy.	2001 Aug	11472315
Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity.	2001 Aug 30	11520209
5-Aminosalicylic acid protection against oxidative damage to synaptosomal membranes by alkoxyl radicals in vitro.	2001 Jan	11358278
[Therapeutic principles for chronic inflammatory bowel disease].	2001 Jan 1	11586666
Recurrent atypical myxoid fibroepithelial polyp associated with vulvar Crohn's disease.	2001 Jul	11444204
Acute renal failure in a 53-year-old woman with Crohn's disease treated with 5-aminosalicylic acid.	2001 Jul	11431204
Comparison of 5-amino salicylic acid plus glucocorticosteroid with metronidazole and ciprofloxacin in patients with active ulcerative colitis.	2001 Jul	11418802
Oral balsalazide (Colazal) for ulcerative colitis.	2001 Jul 23	11468602
Ulcerative colitis associated with interferon treatment for chronic hepatitis C.	2001 Jun	11451187
[A case of successful mesalazine enema for rectal cavitating ulcer of Crohn's disease].	2001 Jun	11436282
Probiotics (Br J Surg 2001; 88: 161-2).	2001 Jun	11412272
5-Aminosalicylates in inflammatory bowel disease: choosing the right dose.	2001 Jun-Jul	11529648
What can nephrologists learn from epidemiology?	2001 Mar-Apr	11411019
Inflammatory bowel disease and pregnancy.	2001 May	11383588
Crohn's disease of the esophagus: clinical features and outcomes.	2001 May	11383583
Familial microscopic colitis.	2001 May	11381303
Conventional treatment of Crohn's disease: objectives and outcomes.	2001 May	11380039
[Interstitial nephritis after treatment with mesalazine in the patient with ulcerative colitis].	2001 May 10	11460356
Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagent.	2001 May 4	11382289
Salvage external beam radiotherapy for clinical failure after cryosurgery for prostate cancer.	2001 Nov 1	11597801
Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug.	2001 Oct	11587223
Recent advances in the treatment of the seronegative spondyloarthropathies.	2001 Oct	11564371
Review article: balsalazide therapy in ulcerative colitis.	2001 Oct	11563993
Olsalazine is not superior to placebo in maintaining remission of inactive Crohn's colitis and ileocolitis: a double blind, parallel, randomised, multicentre study.	2001 Oct	11559654
Mesalamine induces manganese superoxide dismutase in rat intestinal epithelial cell lines and in vivo.	2001 Oct	11557525
[Collagenous colitis. A study of 11 cases].	2001 Sep	11593141
Headache during mesalamine therapy: a case report of mesalamine-induced pseudotumor cerebri.	2001 Sep	11593133
Acute pericarditis associated with 5-aminosalicylic acid (5-ASA) treatment for severe active ulcerative colitis.	2001 Sep	11579953
The hair of the dog.	2001 Sep	11569714
[Generalized pustulous psoriasis: A novel extraintestinal manifestation of Crohn's disease?].	2001 Sep	11558073
Review article: current therapeutic options for radiation proctopathy.	2001 Sep	11552895
NO-mesalamine protects colonic epithelial cells against apoptotic damage induced by proinflammatory cytokines.	2001 Sep	11518677
Drug points: Hypersensitivity reaction to balsalazide.	2001 Sep 1	11532843
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].	2001 Sep 13	11599291
Guided self-management and patient-directed follow-up of ulcerative colitis: a randomised trial.	2001 Sep 22	11583752
5-Aminosalicylate stimulates phospholipase D activity in macrophages.	2001 Sep 28	11566448

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Ulcerative Colitis - Active ORAL: 250 and 500 mg capsules: 1 g orally 4 times a day Duration of therapy: Up to 8 weeks 400 mg tablets: 800 mg orally 3 times a day Duration of therapy: 6 weeks 400 mg delayed release capsules: 800 mg orally 3 times a day Duration of therapy: 6 weeks 800 mg delayed release tablets: 1600 mg orally 3 times a day Duration of therapy: 6 weeks 1200 mg tablets: 2.4 to 4.8 g orally once a day with food

Route of Administration: Oral

In Vitro Use Guide

Treatment of both HT-29 wild-type, dominant-negative PPARg and empty vector cells HT-29 cells with Mesalamine (30 mM) for 48 h increased the activity of PPARg

Name

Type

Language

MESALAMINE

Official Name

English

MESALAMINE [VANDF]

Common Name

English

MESALAMINE [HSDB]

Common Name

English

MESALAZINE [INN]

Common Name

English

FISALAMINE

Common Name

English

ASACOL

Brand Name

English

MESALAMINE [USP]

Common Name

English

MESALAZINE [JAN]

Common Name

English

ROWASA

Brand Name

English

MESALAMINE [MI]

Common Name

English

MESALAZINE [EP]

Common Name

English

5-AMINOSALICYLIC ACID

Systematic Name

English

APRISO

Brand Name

English

NSC-38877

Code

English

5-AMINO-2-HYDROXYBENZOIC ACID

Systematic Name

English

BENZOIC ACID, 5-AMINO-2-HYDROXY-

Common Name

English

5-ASA

Common Name

English

PENTASA

Brand Name

English

MESALAZINE [WHO-DD]

Common Name

English

MESALAZINE [MART.]

Common Name

English

SFROWASA

Brand Name

English

MESALAMINE [USAN]

Common Name

English

LIALDA

Brand Name

English

MAX-002

Code

English

MESALAZINE

Official Name

English

MESALAMINE [ORANGE BOOK]

Common Name

English

MESALAMINE [USP-RS]

Common Name

English

CANASA

Brand Name

English

IIALDA

Brand Name

English

M-AMINOSALICYLIC ACID

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QA07EC02