CHEBI:267413 - balsalazide

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ChEBI Name balsalazide
Definition A monohydroxybenzoic acid consisting of 5-aminosalicylic acid (mesalazine) linked to 4-aminobenzoyl-β-alanine via an azo bond.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H15N3O6
Net Charge 0
Average Mass 357.31750
Monoisotopic Mass 357.09609
InChI 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+
SMILES OC(=O)CCNC(=O)c1ccc(cc1)\N=N\c1ccc(O)c(c1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
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ChEBI Ontology
Outgoing balsalazide (CHEBI:267413) has role anti-ulcer drug (CHEBI:49201)
balsalazide (CHEBI:267413) has role gastrointestinal drug (CHEBI:55324)
balsalazide (CHEBI:267413) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
balsalazide (CHEBI:267413) has role prodrug (CHEBI:50266)
balsalazide (CHEBI:267413) is a monohydroxybenzoic acid (CHEBI:25389)
balsalazide (CHEBI:267413) is conjugate acid of balsalazide(2−) (CHEBI:59165)
Incoming balsalazide disodium (CHEBI:59164) has functional parent balsalazide (CHEBI:267413)
balsalazide(2−) (CHEBI:59165) is conjugate base of balsalazide (CHEBI:267413)
5-[(E)-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazenyl]-2-hydroxybenzoic acid
INNs Sources
balsalazida ChemIDplus
balsalazide ChemIDplus
balsalazidum ChemIDplus
Synonyms Sources
(E)-5-((4-(((2-carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acid ChemIDplus
(E)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acid ChEBI
3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid IUPAC
5-[4-(2-carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acid ChEBI
balsalazido ChemIDplus
Manual Xrefs Databases
284 DrugCentral
Balsalazide Wikipedia
DB01014 DrugBank
GB2080796 Patent
US4412992 Patent
View more database links
Registry Numbers Types Sources
80573-04-2 CAS Registry Number ChemIDplus
8081576 Beilstein Registry Number Beilstein
8081576 Reaxys Registry Number Reaxys
Last Modified
22 February 2017
General Comment
2011-03-23 Balsalazide is a prodrug, releasing the anti-inflammatory mesalazine in the large intestine. Generally administered as its disodium salt, it is used in the treatment of ulcerative colitis.