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
SMILES
OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C2=CC=C(O)C(=C2)C(O)=O
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+
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 |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/balsalazide.html
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0019369 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | COLAZAL Approved UseCOLAZAL 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 Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
344 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1931 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19633577 |
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
Dose | Population | Adverse 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) Sources: Urticaria (1 patient) |
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%) Sources: Page: p. 61Nausea (2%) Vomiting (1%) Erythema nodosum (1%) Frequent bowel movements (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no | ||||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
Page: 11.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 381.4 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Km 188.9 uM] | ||||
yes [Km 55.1 uM] | ||||
yes [Km 77.4 uM] | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Balsalazide-induced myocarditis. | 2008 Nov 28 |
|
Unilateral balsalazide-induced eosinophilic pneumonia in an ulcerative colitis patient. | 2010 Sep |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15735431
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
Edited
Sat Dec 16 15:59:25 GMT 2023
by
admin
on
Sat Dec 16 15:59:25 GMT 2023
|
Record UNII |
P80AL8J7ZP
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C257
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
NDF-RT |
N0000005760
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
NDF-RT |
N0000005760
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
NDF-RT |
N0000005760
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
WHO-ATC |
A07EC04
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
LIVERTOX |
88
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
WHO-VATC |
QA07EC04
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
NDF-RT |
N0000175781
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
||
|
NDF-RT |
N0000005760
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
Balsalazide
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
SUB06092MIG
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
DTXSID7040653
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
CHEMBL1201346
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
P80AL8J7ZP
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
284
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
18747
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | RxNorm | ||
|
DB01014
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
m2208
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | Merck Index | ||
|
80573-04-2
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
C038637
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
P80AL8J7ZP
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
100000088406
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
BALSALAZIDE
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
267413
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
C65247
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
PRIMARY | |||
|
5221
Created by
admin on Sat Dec 16 15:59:26 GMT 2023 , Edited by admin on Sat Dec 16 15:59:26 GMT 2023
|
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 |