U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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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
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/mtm/mesalamine.html

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

Curator's Comment: Mesalazine and acetyl mesalazine do not cross the blood brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COLAZAL

Approved Use

COLAZAL is indicated for the treatment of mildly to moderately active ulcerative colitis in patients 5 years of age and older. Safety and effectiveness of COLAZAL beyond 8 weeks in children (ages 5-17 years) and 12 weeks in adults have not been established. •COLAZAL is a locally acting aminosalicylate indicated for the treatment of mildly to moderately active ulcerative colitis in patients 5 years of age and older. (1) •Safety and effectiveness of COLAZAL beyond 8 weeks in children (ages 5-17 years) and 12 weeks in adults have not been established. (1)

Launch Date

2000
Primary
PENTASA

Approved Use

PENTASA is indicated for the induction of remission and for the treatment of patients with mildly to moderately active ulcerative colitis.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
857 ng/mL
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
1595 ng/mL
2.4 g single, oral
dose: 2.4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
2154 ng/mL
4.8 g single, oral
dose: 4.8 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
150 ng/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
452 ng/mL
6.75 mg 1 times / day multiple, oral
dose: 6.75 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BALSALAZIDE plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
344 ng/mL
6.25 mg 1 times / day multiple, oral
dose: 6.25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9578 ng × h/mL
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
21084 ng × h/mL
2.4 g single, oral
dose: 2.4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
44775 ng × h/mL
4.8 g single, oral
dose: 4.8 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
909 ng × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
2031 ng × h/mL
6.75 mg 1 times / day multiple, oral
dose: 6.75 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BALSALAZIDE plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
1931 ng × h/mL
6.25 mg 1 times / day multiple, oral
dose: 6.25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.56 h
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
7.05 h
2.4 g single, oral
dose: 2.4 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
7.25 h
4.8 g single, oral
dose: 4.8 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
25 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
57%
1.2 g single, oral
dose: 1.2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
MESALAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
6.75 g 1 times / day multiple, oral
Dose: 6.75 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.75 g, 1 times / day
Sources:
unhealthy, 12.8 years (range: 5-17 years)
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Sources:
Disc. AE: Abdominal pain, Urticaria...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (1 patient)
Urticaria (1 patient)
Sources:
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Colitis ulcerative, Nausea...
AEs leading to
discontinuation/dose reduction:
Colitis ulcerative (2.4%)
Nausea (2%)
Vomiting (1%)
Erythema nodosum (1%)
Frequent bowel movements (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 1 patient
Disc. AE
6.75 g 1 times / day multiple, oral
Dose: 6.75 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.75 g, 1 times / day
Sources:
unhealthy, 12.8 years (range: 5-17 years)
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Sources:
Urticaria 1 patient
Disc. AE
6.75 g 1 times / day multiple, oral
Dose: 6.75 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.75 g, 1 times / day
Sources:
unhealthy, 12.8 years (range: 5-17 years)
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Sources:
Erythema nodosum 1%
Disc. AE
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
Frequent bowel movements 1%
Disc. AE
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
Vomiting 1%
Disc. AE
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
Nausea 2%
Disc. AE
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
Colitis ulcerative 2.4%
Disc. AE
6.6 g 1 times / day multiple, oral
Recommended
Dose: 6.6 g, 1 times / day
Route: oral
Route: multiple
Dose: 6.6 g, 1 times / day
Sources:
unhealthy, adult
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
unlikely
unlikely
unlikely
unlikely
unlikely
weak [IC50 381.4 uM]
yes
yes
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Mesalazine activation of eosinophil.
1997 Oct 11
Maintenance of remission of ulcerative colitis: a comparison between balsalazide 3 g daily and mesalazine 1.2 g daily over 12 months. ABACUS Investigator group.
1998 Dec
Interstitial nephritis in children with Crohn's disease.
2000 Apr
Effects of sulfasalazine and its metabolites on steady state messenger RNA concentrations for inflammatory cytokines, matrix metalloproteinases, and tissue inhibitors of metalloproteinase in rheumatoid synovial fibroblasts.
2000 Mar
Mesalamine-induced chest pain: a case report.
2000 May
Glomerular and tubular renal functions after long-term medication of sulphasalazine, olsalazine, and mesalazine in patients with ulcerative colitis.
2000 Nov
[Early renal failure caused by mesalazine].
2000 Oct
Pyelonephritis caused by mesalazine.
2000 Oct
Tolerability of aminosalicylates in inflammatory bowel disease.
2001
[Hepatotoxicity of medications].
2001 Apr 14
Sulphasalazine inhibits macrophage activation: inhibitory effects on inducible nitric oxide synthase expression, interleukin-12 production and major histocompatibility complex II expression.
2001 Aug
Oral versus combination mesalazine therapy in active ulcerative colitis: a double-blind, double-dummy, randomized multicentre study.
2001 Feb
A novel pH- and time-based multi-unit potential colonic drug delivery system. II. Optimization of multiple response variables.
2001 Feb 1
A novel pH- and time-based multi-unit potential colonic drug delivery system. I. Development.
2001 Feb 1
5-Aminosalicylic acid protection against oxidative damage to synaptosomal membranes by alkoxyl radicals in vitro.
2001 Jan
[Therapy of active Crohn disease with Boswellia serrata extract H 15].
2001 Jan
Can postoperative relapse of Crohn's disease be prevented?
2001 Jan
Once versus divided daily dosing with delayed-release mesalazine: a study of tissue drug concentrations and standard pharmacokinetic parameters.
2001 Jan
Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases?
2001 Jan-Feb
Recurrent atypical myxoid fibroepithelial polyp associated with vulvar Crohn's disease.
2001 Jul
[A case of successful mesalazine enema for rectal cavitating ulcer of Crohn's disease].
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
5-Aminosalicylates in inflammatory bowel disease: choosing the right dose.
2001 Jun-Jul
T-large granular lymphocyte leukemia accompanied by an increase of natural killer cells (CD3-) and associated with ulcerative colitis and autoimmune hepatitis.
2001 Mar
Lymph folliculitis in ulcerative colitis.
2001 Mar
Anti-tumor necrosis factor monoclonal antibody therapy for gastrointestinal Behçet's disease: a case report.
2001 Mar
Minimal renal dysfunction in inflammatory bowel disease is related to disease activity but not to 5-ASA use.
2001 Mar
From the Food and Drug Administration.
2001 Mar 7
Inflammatory bowel disease and pregnancy.
2001 May
Familial microscopic colitis.
2001 May
Conventional treatment of Crohn's disease: objectives and outcomes.
2001 May
A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.
2001 May
Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagent.
2001 May 4
Salvage external beam radiotherapy for clinical failure after cryosurgery for prostate cancer.
2001 Nov 1
Review article: balsalazide therapy in ulcerative colitis.
2001 Oct
Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug.
2001 Oct
[Conservative therapy of severe ulcerative colitis. More effective than internists believe!].
2001 Sep 13
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Balsalazide and/or high-potency probiotic mixture (VSL#3) in maintaining remission after attack of acute, uncomplicated diverticulitis of the colon.
2007 Sep
Balsalazide-induced myocarditis.
2008 Nov 28
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be used rectally
Three 750 mg COLAZAL capsules to be taken three times a day for a total daily dose of 6.75 grams for a duration of 8 weeks. Some patients in the clinical trials required treatment for up to 12 weeks.
Route of Administration: Oral
Mean equivalent doses (0.1 to 10 mM) of balsalazide (range, 6.3 +/- 1.5 to 16.7 +/- 1.3 microA/cm2) significantly stimulated (P < 0.001) secretion in rabbit distal ileum. The value for the effective dose that is half the maximal dose for secretion induced by 0.9 mM.
Name Type Language
MESALAZINE
EP   INN   JAN   MART.   WHO-DD  
INN  
Preferred Name English
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 [EP MONOGRAPH]
Common Name English
mesalazine [INN]
Common Name English
MESALAMINE [USP MONOGRAPH]
Common Name English
FISALAMINE
Common Name English
ASACOL
Brand Name English
MESALAZINE [JAN]
Common Name English
ROWASA
Brand Name English
MESALAMINE [MI]
Common Name English
Mesalazine [WHO-DD]
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
MESALAZINE [EP IMPURITY]
Common Name English
PENTASA
Brand Name English
MESALAZINE [MART.]
Common Name English
SFROWASA
Brand Name English
MESALAMINE [USAN]
Common Name English
LIALDA
Brand Name English
MAX-002
Code 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 Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
LIVERTOX NBK547995
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
FDA ORPHAN DRUG 275909
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
FDA ORPHAN DRUG 298109
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NDF-RT N0000175781
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
NCI_THESAURUS C257
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
WHO-ATC A07EC02
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
FDA ORPHAN DRUG 253607
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C29249
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
LACTMED
Mesalamine
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
MESH
D019804
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
CAS
89-57-6
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-919-1
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
RS_ITEM_NUM
1392705
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
USAN
X-60
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
DRUG CENTRAL
1710
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
SMS_ID
100000091953
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
FDA UNII
4Q81I59GXC
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
NSC
38877
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
HSDB
7512
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
PUBCHEM
4075
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
EVMPD
SUB08782MIG
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID5024506
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
IUPHAR
2700
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
RXCUI
52582
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY RxNorm
CHEBI
6775
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
WIKIPEDIA
MESALAZINE
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
DRUG BANK
DB00244
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
DAILYMED
4Q81I59GXC
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
ChEMBL
CHEMBL704
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
INN
5444
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY
MERCK INDEX
m7244
Created by admin on Wed Apr 02 09:16:22 GMT 2025 , Edited by admin on Wed Apr 02 09:16:22 GMT 2025
PRIMARY Merck Index