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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
[Therapeutic principles for chronic inflammatory bowel disease].
2001 Jan 1
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
Review article: balsalazide therapy in ulcerative colitis.
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
[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
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 Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
NDF-RT N0000005760
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
LIVERTOX 605
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
NDF-RT N0000005760
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
NDF-RT N0000005760
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
NDF-RT N0000005760
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
NDF-RT N0000175781
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
WHO-ATC A07EC02
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
Code System Code Type Description
NCI_THESAURUS
C29249
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
MESH
D019804
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
CAS
89-57-6
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
ECHA (EC/EINECS)
201-919-1
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
HSDB
89-57-6
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
PUBCHEM
4075
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB08782MIG
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
EPA CompTox
89-57-6
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
IUPHAR
2700
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
RXCUI
52582
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY RxNorm
WIKIPEDIA
MESALAZINE
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
DRUG BANK
DB00244
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
LactMed
89-57-6
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
ChEMBL
CHEMBL704
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
INN
5444
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY
MERCK INDEX
M7244
Created by admin on Tue Mar 06 11:00:19 UTC 2018 , Edited by admin on Tue Mar 06 11:00:19 UTC 2018
PRIMARY Merck Index