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

General Information of Drug (ID: DR0681)
Drug Name
Febuxostat
Synonyms
Feburic; Febuxostat; Febuxostat (Uloric); TMX 67; TMX-67; Tei 6720; Tei-6720; Uloric; 101V0R1N2E; 144060-53-7; 2-(3-CYANO-4-ISOBUTOXY-PHENYL)-4-METHYL-5-THIAZOLE-CARBOXYLIC ACID; 2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid; Adenuric; 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid; 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid; C16H16N2O3S; CHEMBL1164729; NCGC00182059-02; UNII-101V0R1N2E
Indication Hyperuricaemia [ICD11: 5C55] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 316.4 Topological Polar Surface Area 111
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
134018
PubChem SID
827254 ; 4484625 ; 7848269 ; 7890737 ; 10243499 ; 12014717 ; 14899120 ; 29311812 ; 46506708 ; 50064429 ; 53197612 ; 57344764 ; 92719385 ; 93307960 ; 99431926 ; 103765728 ; 104142020 ; 104253203 ; 104381153 ; 118047349 ; 119526879 ; 121362144 ; 124757329 ; 124893781 ; 125001903 ; 125164133 ; 125645402 ; 126620851 ; 126652673 ; 126667078 ; 127554532 ; 134338644 ; 135089359 ; 135565727 ; 135692175 ; 135697551 ; 135723459 ; 136367945 ; 136920430 ; 137171680 ; 141631602 ; 144075735 ; 144115972 ; 144206555 ; 151981114 ; 152227348 ; 152258563 ; 152344198 ; 160647398 ; 160813538
ChEBI ID
CHEBI:31596
CAS Number
144060-53-7
TTD Drug ID
D0A5SE
Formula
C16H16N2O3S
Canonical SMILES
CC1=C(SC(=N1)C2=CC(=C(C=C2)OCC(C)C)C#N)C(=O)O
InChI
1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
InChIKey
BQSJTQLCZDPROO-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
Febuxostat acyl-glucuronide DM000153
71316713
Conjugation - Conjugation 1 [3]
Febuxostat metabolite 67M-1 DM000144
9818975
Oxidation - Oxidation 1 [3]
Febuxostat metabolite 67M-2 DM000149
11956739
Oxidation - Oxidation 1 [3]
Febuxostat metabolite 67M-3 DM000152
135482091
Oxidation - Oxidation 1 [3]
Febuxostat metabolite 67M-1 sulfate conjugate DM000146 N. A. Conjugation - Conjugation 2 [5]
Febuxostat metabolite 67M-4(di-carboxylic acid) DM000145
11956740
Oxidation - Oxidation 2 [5]
Febuxostat metabolite 7M-1 glucuronide DM000148 N. A. Conjugation - Conjugation 2 [5]
Febuxostat metabolite 7M-2 glucuronide DM000151 N. A. Reduction - Reduction 2 [5]
Febuxostat metabolite Dehydrated 67M-1 glucuronide DM000147 N. A. Other reaction - Dehydration 2 [5]
Febuxostat metabolite Dehydrated 67M-2 glucuronide DM000150 N. A. Other reaction - Dehydration 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003399 Febuxostat Febuxostat metabolite 67M-1 Oxidation - Oxidation CYP2C9 [3]
MR003400 Febuxostat Febuxostat metabolite 67M-2 Oxidation - Oxidation CYP1A1 ... [3]
MR003401 Febuxostat Febuxostat metabolite 67M-3 Oxidation - Oxidation CYP1A1 [3]
MR003402 Febuxostat Febuxostat acyl-glucuronide Conjugation - Conjugation Unclear [3]
MR003393 Febuxostat metabolite 67M-1 Febuxostat metabolite 67M-4(di-carboxylic acid) Oxidation - Oxidation Unclear [5]
MR003394 Febuxostat metabolite 67M-1 Febuxostat metabolite 67M-1 sulfate conjugate Conjugation - Conjugation Unclear [5]
MR003395 Febuxostat metabolite 67M-1 Febuxostat metabolite Dehydrated 67M-1 glucuronide Other reaction - Dehydration Unclear [5]
MR003396 Febuxostat metabolite 67M-1 Febuxostat metabolite 7M-1 glucuronide Conjugation - Conjugation Unclear [5]
MR003397 Febuxostat metabolite 67M-2 Febuxostat metabolite Dehydrated 67M-2 glucuronide Other reaction - Dehydration Unclear [5]
MR003398 Febuxostat metabolite 67M-2 Febuxostat metabolite 7M-2 glucuronide Reduction - Reduction Unclear [5]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [4]
⏷ Show the Full List of 18  DME(s)
References
1 Febuxostat was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro drug-drug interaction studies with febuxostat, a novel non-purine selective inhibitor of xanthine oxidase: plasma protein binding, identification of metabolic enzymes and cytochrome P450 inhibition Xenobiotica. 2008 May;38(5):496-510. doi: 10.1080/00498250801956350.
3 In vitro drug-drug interaction studies with febuxostat, a novel non-purine selective inhibitor of xanthine oxidase: plasma protein binding, identification of metabolic enzymes and cytochrome P450 inhibition. Xenobiotica. 2008 May;38(5):496-510.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Metabolism and excretion of [14C] febuxostat, a novel nonpurine selective inhibitor of xanthine oxidase, in healthy male subjects J Clin Pharmacol. 2011 Feb;51(2):189-201. doi: 10.1177/0091270010365549.

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