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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 of MESALAMINE

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.
2001
TNF-alpha induced endothelial MAdCAM-1 expression is regulated by exogenous, not endogenous nitric oxide.
2001
Tolerability of aminosalicylates in inflammatory bowel disease.
2001
[The new experimental ulcerative colitis model in rats induced by subserosal injection of acetic acid].
2001 Aug
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.
2001 Aug
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
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
The expression of IL-12 p40 and its homologue, Epstein-Barr virus-induced gene 3, in inflammatory bowel disease.
2001 Aug
Inflammatory pseudotumor of the liver as the first manifestation of Crohn's disease.
2001 Aug
Adult fibrosing colonopathy associated with mesalazine treatment.
2001 Aug
[Metastatic Crohn's disease in childhood].
2001 Aug
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
Renal tubular injury is present in acute inflammatory bowel disease prior to the introduction of drug therapy.
2001 Aug
Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity.
2001 Aug 30
[Therapeutic principles for chronic inflammatory bowel disease].
2001 Jan 1
Recurrent atypical myxoid fibroepithelial polyp associated with vulvar Crohn's disease.
2001 Jul
Acute renal failure in a 53-year-old woman with Crohn's disease treated with 5-aminosalicylic acid.
2001 Jul
Comparison of 5-amino salicylic acid plus glucocorticosteroid with metronidazole and ciprofloxacin in patients with active ulcerative colitis.
2001 Jul
Mesalamine-induced unilateral eosinophilic pneumonia.
2001 Jul
Oral balsalazide (Colazal) for ulcerative colitis.
2001 Jul 23
Ulcerative colitis associated with interferon treatment for chronic hepatitis C.
2001 Jun
[A case of successful mesalazine enema for rectal cavitating ulcer of Crohn's disease].
2001 Jun
Infliximab for the treatment of Crohn's disease: review and indications for clinical use in Canada.
2001 Jun
Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation.
2001 Jun
Lacrimal gland inflammation as the presenting sign of Crohn's disease.
2001 Jun
Probiotics (Br J Surg 2001; 88: 161-2).
2001 Jun
Diversion colitis in children with colovaginoplasty.
2001 Jun
In vitro effects of E3040, a dual inhibitor of 5-lipoxygenase and thromboxane A(2) synthetase, on eicosanoid production.
2001 Jun 22
5-Aminosalicylates in inflammatory bowel disease: choosing the right dose.
2001 Jun-Jul
What can nephrologists learn from epidemiology?
2001 Mar-Apr
Impact of different therapeutic regimens on the outcome of patients with Crohn's disease of the upper gastrointestinal tract.
2001 May
Inflammatory bowel disease and pregnancy.
2001 May
[Interstitial nephritis after treatment with mesalazine in the patient with ulcerative colitis].
2001 May 10
Salvage external beam radiotherapy for clinical failure after cryosurgery for prostate cancer.
2001 Nov 1
Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug.
2001 Oct
Recent advances in the treatment of the seronegative spondyloarthropathies.
2001 Oct
Review article: balsalazide therapy in ulcerative colitis.
2001 Oct
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
Mesalamine induces manganese superoxide dismutase in rat intestinal epithelial cell lines and in vivo.
2001 Oct
[Collagenous colitis. A study of 11 cases].
2001 Sep
Headache during mesalamine therapy: a case report of mesalamine-induced pseudotumor cerebri.
2001 Sep
Acute pericarditis associated with 5-aminosalicylic acid (5-ASA) treatment for severe active ulcerative colitis.
2001 Sep
The hair of the dog.
2001 Sep
[Generalized pustulous psoriasis: A novel extraintestinal manifestation of Crohn's disease?].
2001 Sep
Review article: current therapeutic options for radiation proctopathy.
2001 Sep
NO-mesalamine protects colonic epithelial cells against apoptotic damage induced by proinflammatory cytokines.
2001 Sep
Drug points: Hypersensitivity reaction to balsalazide.
2001 Sep 1
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].
2001 Sep 13
Guided self-management and patient-directed follow-up of ulcerative colitis: a randomised trial.
2001 Sep 22
5-Aminosalicylate stimulates phospholipase D activity in macrophages.
2001 Sep 28
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
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
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
EP   INN   JAN   MART.   WHO-DD  
INN  
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
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
FDA ORPHAN DRUG 253607
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
LIVERTOX 605
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
FDA ORPHAN DRUG 275909
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
FDA ORPHAN DRUG 298109
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NDF-RT N0000175781
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
NCI_THESAURUS C257
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
WHO-ATC A07EC02
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C29249
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
MESH
D019804
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
CAS
89-57-6
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
ECHA (EC/EINECS)
201-919-1
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
HSDB
89-57-6
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
PUBCHEM
4075
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
EVMPD
SUB08782MIG
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
EPA CompTox
89-57-6
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
IUPHAR
2700
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
RXCUI
52582
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
MESALAZINE
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
DRUG BANK
DB00244
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
LactMed
89-57-6
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
ChEMBL
CHEMBL704
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
INN
5444
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY
MERCK INDEX
M7244
Created by admin on Tue Oct 22 00:22:32 UTC 2019 , Edited by admin on Tue Oct 22 00:22:32 UTC 2019
PRIMARY Merck Index