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

General Information of Drug (ID: DR1628)
Drug Name
Tranilast
Synonyms
Tranilast (SB 252218); Tranilast [USAN:INN:JAN]; Tranilastum; Tranilastum [INN-Latin]; Tranpro; tranilast; HVF50SMY6E; MK 341; MK-341; NZHGWWWHIYHZNX-CSKARUKUSA-N; Rizaben; SB-252218; trans-Tranilast; 2-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid; 3,4-DAA; 53902-12-8; 70806-55-2; Anthranilic acid, N-(3,4-dimethoxycinnamoyl)-; C18H17NO5; CHEBI:77572; MFCD00864787; MLS000028468; N-(3,4-Dimethoxycinnamoyl)anthranilic acid; UNII-HVF50SMY6E; n-(3',4'-dimethoxycinnamoyl) anthranilic acid
Indication Conjunctivitis [ICD11: 9A60] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 327.3 Topological Polar Surface Area 84.9
Heavy Atom Count 24 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5282230
PubChem SID
855567 ; 7849089 ; 8616956 ; 12013287 ; 14801725 ; 17405845 ; 24278719 ; 26612911 ; 26680238 ; 26719641 ; 26759646 ; 39315705 ; 46386750 ; 47589114 ; 47810891 ; 47885539 ; 48416652 ; 49645767 ; 49684379 ; 49700724 ; 49887093 ; 50103918 ; 50103919 ; 50103920 ; 53778299 ; 56422140 ; 57288861 ; 57358583 ; 75624513 ; 85231347 ; 85789432 ; 87870631 ; 89850281 ; 90341124 ; 92303237 ; 92308202 ; 92308335 ; 92308903 ; 92711430 ; 99437152 ; 99444086 ; 103330746 ; 107388281 ; 113856723 ; 118303066 ; 121362071 ; 124637814 ; 124757248 ; 124799410 ; 124883425
ChEBI ID
CHEBI:77572
CAS Number
53902-12-8
TTD Drug ID
D0E6OC
Formula
C18H17NO5
Canonical SMILES
COC1=C(C=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O)OC
InChI
1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+
InChIKey
NZHGWWWHIYHZNX-CSKARUKUSA-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-demethyltranilast DM005797
53816044
Oxidation - 4-demethylation 1 [2] , [4]
Tranilast glucuronide DM005800 N. A. Conjugation - Glucuronidation 1 [2] , [4]
Tranilast metabolite N-4 DM005801
53664003
Oxidation - Demethylation 1 [4]
Tranilast metabolite N-3-G DM005799 N. A. Conjugation - Glucuronidation 2 [2] , [4]
Tranilast metabolite N-3-S DM005798 N. A. Unclear 2 [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006194 Tranilast 4-demethyltranilast Oxidation - 4-demethylation CYP2C9 [2], [4]
MR006197 Tranilast Tranilast glucuronide Conjugation - Glucuronidation UGT1A1 [2], [4]
MR006198 Tranilast Tranilast metabolite N-4 Oxidation - Demethylation CYP2C9 [4]
MR006195 4-demethyltranilast Tranilast metabolite N-3-S Unclear Unclear [2], [4]
MR006196 4-demethyltranilast Tranilast metabolite N-3-G Conjugation - Glucuronidation Unclear [2], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2] , [4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
References
1 ClinicalTrials.gov (NCT00818805) Efficacy Investigation Study of Olopatadine Hydrochloride Ophthalmic Solution Using OHIO Chamber in Patients With Seasonal Allergic Rhinitis (SAR).
2 Glucuronidation of antiallergic drug, Tranilast: identification of human UDP-glucuronosyltransferase isoforms and effect of its phase I metabolite. Drug Metab Dispos. 2007 Apr;35(4):583-9.
3 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
4 Simultaneous determination of tranilast and metabolites in plasma and urine using high-performance liquid chromatography
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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