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Details

Stereochemistry ACHIRAL
Molecular Formula C17H13N3O6.2Na.2H2O
Molecular Weight 437.3124
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BALSALAZIDE DISODIUM

SMILES

c1cc(ccc1C(=O)NCCC(=O)[O-])/N=N/c2ccc(c(c2)C(=O)O)[O-].[Na+].[Na+].O.O

InChI

InChIKey=XDCNKOBSQURQOZ-MVIJUDHYSA-L
InChI=1S/C17H15N3O6.2Na.2H2O/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);;;2*1H2/q;2*+1;;/p-2/b20-19+;;;;

HIDE SMILES / InChI

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H15N3O6
Molecular Weight 357.3182
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/pro/balsalazide.html

Balsalazide, a prodrug that is enzymatically cleaved by bacterial azoreduction to release equimolar quantities of mesalamine (5-aminosalicylic acid or 5-ASA) in the colon, an anti-inflammatory drug. The mechanism of action of 5-ASA is unknown, but appears to be local to the colonic mucosa rather than systemic. Balsalazide is indicated for the treatment of mildly to moderately active ulcerative colitis. Most frequently reported adverse events are: headache, abdominal pain, diarrhea, nausea, vomiting, respiratory infection, and arthralgia. The use of orally administered antibiotics could, theoretically, interfere with the release of mesalamine in the colon.

Approval Year

Targets

Targets

Conditions

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

9.6387839E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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)
n = 33
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Population Size: 33
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
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: Page: p. 61
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)
n = 33
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Population Size: 33
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)
n = 33
Health Status: unhealthy
Age Group: 12.8 years (range: 5-17 years)
Sex: M+F
Population Size: 33
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
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: Page: p. 61
unhealthy, adult
n = 210
Health Status: unhealthy
Age Group: adult
Population Size: 210
Sources: Page: p. 61
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug 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
weak [IC50 381.4 uM]
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
Review article: balsalazide therapy in ulcerative colitis.
2001 Oct
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
[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

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 Fri Jun 25 21:04:47 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:47 UTC 2021
Record UNII
1XL6BJI034
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BALSALAZIDE DISODIUM
ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
BALSALAZIDE SODIUM
Common Name English
BALSALAZIDE DISODIUM [USAN]
Common Name English
COLAZIDE
Brand Name English
BX661A
Code English
BALSALAZIDE DISODIUM SALT DIHYDRATE [MI]
Common Name English
BALSALAZIDE DISODIUM SALT DIHYDRATE
MI  
Common Name English
COLAZAL
Brand Name English
BALSALAZIDE DISODIUM DIHYDRATE
WHO-DD  
Common Name English
BX-661A
Code English
BENZOIC ACID, 5-((1E)-(4-(((2-CARBOXYETHYL)AMINO)CARBONYL)PHENYL)AZO)-2-HYDROXY-, DISODIUM SALT, DIHYDRATE
Common Name English
BALSALAZIDE DISODIUM [VANDF]
Common Name English
BALSALAZIDE DISODIUM DIHYDRATE [WHO-DD]
Common Name English
BENZOIC ACID, 5-((4-(((2-CARBOXYETHYL)AMINO)CARBONYL)PHENYL)AZO)-2-HYDROXY-, DISODIUM SALT, DIHYDRATE, (E)-
Common Name English
NSC-760046
Code English
(E)-5-((P-((2-CARBOXYETHYL)CARBAMOYL)PHENYL)AZO)SALICYLIC ACID, DISODIUM SALT, DIHYDRATE
Common Name English
BALSALAZIDE DISODIUM [ORANGE BOOK]
Common Name English
BALSALAZIDE DISODIUM [USP-RS]
Common Name English
BALSALAZIDE DISODIUM [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
FDA ORPHAN DRUG 208205
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
Code System Code Type Description
EVMPD
SUB35314
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201346
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
CAS
150399-21-6
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
NCI_THESAURUS
C47409
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
USP_CATALOG
1048255
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY USP-RS
FDA UNII
1XL6BJI034
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
RXCUI
153718
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT000835
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY
MERCK INDEX
M2208
Created by admin on Fri Jun 25 21:04:47 UTC 2021 , Edited by admin on Fri Jun 25 21:04:47 UTC 2021
PRIMARY Merck Index
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ACTIVE MOIETY