U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C17H15N3O6
Molecular Weight 357.3175
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BALSALAZIDE

SMILES

OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C2=CC(C(O)=O)=C(O)C=C2

InChI

InChIKey=IPOKCKJONYRRHP-FMQUCBEESA-N
InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+

HIDE SMILES / InChI

Molecular Formula C17H15N3O6
Molecular Weight 357.3175
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
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
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
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
[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
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
[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
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
Recent advances in the treatment of the seronegative spondyloarthropathies.
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
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
[Effect of balsalazide on intestinal mucosal permeability of dextran sulfate sodium-induced colitis in mice].
2009 Mar
Safety, efficacy, and pharmacokinetics of balsalazide in pediatric patients with mild-to-moderate active ulcerative colitis: results of a randomized, double-blind study.
2009 Nov
Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis.
2009 Oct
Unilateral balsalazide-induced eosinophilic pneumonia in an ulcerative colitis patient.
2010 Sep
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:59:38 GMT 2025
Edited
by admin
on Wed Apr 02 06:59:38 GMT 2025
Record UNII
P80AL8J7ZP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BALSALAZIDE [MI]
Preferred Name English
BALSALAZIDE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
balsalazide [INN]
Common Name English
BALSALAZIDE [VANDF]
Common Name English
5-((4-((2-CARBOXYETHYL)CARBAMOYL)PHENYL)DIAZENYL)-2-HYDROXYBENZOIC ACID
Systematic Name English
Balsalazide [WHO-DD]
Common Name English
BENZOIC ACID, 5-((4-(((2-CARBOXYETHYL)AMINO)CARBONYL)PHENYL)AZO)-2-HYDROXY-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
WHO-ATC A07EC04
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
LIVERTOX 88
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
WHO-VATC QA07EC04
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
NDF-RT N0000175781
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
NDF-RT N0000005760
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
Code System Code Type Description
LACTMED
Balsalazide
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
EVMPD
SUB06092MIG
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID7040653
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201346
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
DAILYMED
P80AL8J7ZP
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
DRUG CENTRAL
284
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
RXCUI
18747
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB01014
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
MERCK INDEX
m2208
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY Merck Index
CAS
80573-04-2
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
MESH
C038637
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
FDA UNII
P80AL8J7ZP
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
SMS_ID
100000088406
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
WIKIPEDIA
BALSALAZIDE
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
CHEBI
267413
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
NCI_THESAURUS
C65247
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
INN
5221
Created by admin on Wed Apr 02 06:59:38 GMT 2025 , Edited by admin on Wed Apr 02 06:59:38 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
AMOUNT ADMINISTERED
FECAL
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY