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Details

Stereochemistry ACHIRAL
Molecular Formula C17H15N3O6
Molecular Weight 357.3175
Optical Activity UNSPECIFIED
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

Description

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

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis.
2009 Oct
Patents

Sample Use Guides

In Vivo Use Guide
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
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
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 [MI]
Common 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 Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
WHO-ATC A07EC04
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
LIVERTOX 88
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
WHO-VATC QA07EC04
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
NDF-RT N0000175781
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
NDF-RT N0000005760
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
Code System Code Type Description
EVMPD
SUB06092MIG
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
EPA CompTox
80573-04-2
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL1201346
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
LactMed
80573-04-2
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
RXCUI
18747
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB01014
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
MERCK INDEX
M2208
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY Merck Index
CAS
80573-04-2
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
MESH
C038637
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
WIKIPEDIA
BALSALAZIDE
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
NCI_THESAURUS
C65247
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY
INN
5221
Created by admin on Tue Oct 22 00:11:19 UTC 2019 , Edited by admin on Tue Oct 22 00:11:19 UTC 2019
PRIMARY