Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2414)
Drug Name
Balsalazide
Prodrug Info Balsalazide is the prodrug of Mesalazine
Synonyms
Balsalazida; Balsalazida [Spanish]; Balsalazide Disodium; Balsalazide [INN:BAN]; Balsalazido; Balsalazido [Spanish]; Balsalazidum; Balsalazidum [Latin]; BX-661A; Colazide; BALSALAZIDE; P80AL8J7ZP; (E)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acid; (E)-5-((4-((2-Carboxyethyl)carbamoyl)phenyl)diazenyl)-2-hydroxybenzoic acid; (E)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acid; 80573-04-2; C17H15N3O6; CHEBI:267413; UNII-P80AL8J7ZP
Indication Ulcerative colitis [ICD11: DD71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 357.32 Topological Polar Surface Area 149
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
54585
ChEBI ID
CHEBI:267413
CAS Number
80573-04-2
Formula
C17H15N3O6
Canonical SMILES
C1=CC(=CC=C1C(=O)NCCC(=O)O)N=NC2=CC(=C(C=C2)O)C(=O)O
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)
InChIKey
IPOKCKJONYRRHP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-aminobenzoyl-(beta)-alanine DM015343
719629
Unclear - Unclear 1 [5]
4-aminobenzoyl-(beta)-alanine DM015343
719629
Unclear - Unclear 1 [6]
Mesalazine DM000380
4075
Unclear - Unclear 1 [5]
Mesalazine DM000380
4075
Unclear - Unclear 1 [6]
N-acetyl mesalazine DM000381
65512
Unclear - Unclear 2 [5]
N-acetyl-4-aminobenzoyl-(beta)-alanine DM017958 N. A. Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009685 Balsalazide 5-aminosalicylic acid Unclear - Unclear NQO1 [5]
MR009687 Balsalazide 4-aminobenzoyl-(beta)-alanine Unclear - Unclear Unclear [5]
MR009688 4-aminobenzoyl-(beta)-alanine N-acetyl-4-aminobenzoyl-(beta)-alanine Unclear - Unclear Unclear [5]
MR009686 5-aminosalicylic acid N-acetyl mesalazine Unclear - Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Azoreductase (azoR) DME1096 Escherichia coli
AZOR_ECOLI
1.7.1.6
[2]
FMN-dependent NADH-azoreductase (azoR1) DME2104 Pseudomonas aeruginosa
AZOR1_PSEAE
1.7.1.17
[3] , [4]
References
1 ClinicalTrials.gov (NCT00486031) Open-Label, Long-term Balsalziade Disodium Tablet Ulcerative Colitis Study
2 Studies of two novel sulfasalazine analogs, ipsalazide and balsalazide. Dig Dis Sci. 1983 Jul;28(7):609-15.
3 Role of tyrosine 131 in the active site of paAzoR1, an azoreductase with specificity for the inflammatory bowel disease prodrug balsalazide. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2010 Jan 1;66(Pt 1):2-7.
4 Arylamine N-acetyltransferases: from drug metabolism and pharmacogenetics to drug discovery. Br J Pharmacol. 2014 Jun;171(11):2705-25.
5 U. S. FDA Label -Balsalazide
6 Mesenteric organ production, hepatic metabolism, and renal elimination of norepinephrine and its metabolites in humans

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