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

General Information of Drug (ID: DR0844)
Drug Name
Ibuprofen
Synonyms
Ibufen; Ibumetin; Ibuprocin; Ibuprohm; Inabrin; Lamidon; Liptan; Medipren; Motrin; Mynosedin; Napacetin; Nobfelon; Nobfen; Nobgen; Andran; Anflagen; Apsifen; Bluton; Brufanic; Brufen; Brufort; Buburone; Butylenin; Dolgit; Ebufac; Epobron; Haltran; Ibu-slo; Nuprin; Nurofen; Pantrop; PediaProfen; Rebugen; Roidenin; Suspren; Tabalon; Trendar; ibuprofen; p-Isobutylhydratropic acid; (RS)-Ibuprofen; 15687-27-1; 2-(4-Isobutylphenyl)propanoic acid; 2-[4-(2-methylpropyl)phenyl]propanoic acid; 4-Isobutylhydratropic acid; Adran; Advil; Anco; Ibren; Rufen; Urem
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 206.28 Topological Polar Surface Area 37.3
Heavy Atom Count 15 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3672
PubChem SID
4743 ; 138460 ; 611158 ; 855602 ; 3140375 ; 7647311 ; 7847194 ; 7979568 ; 8062120 ; 8147017 ; 8149384 ; 8152318 ; 10509306 ; 11152950 ; 11336062 ; 11361301 ; 11363743 ; 11366305 ; 11368867 ; 11371490 ; 11373528 ; 11377029 ; 11406458 ; 11462273 ; 11483914 ; 11487945 ; 11490281 ; 11491830 ; 11494663 ; 14822381 ; 17405252 ; 24277715 ; 24896130 ; 25623341 ; 26611780 ; 26679534 ; 26747223 ; 26747224 ; 26752326 ; 26758921 ; 29222795 ; 46507255 ; 47217047 ; 47515579 ; 47885643 ; 47959999 ; 48413891 ; 48416098 ; 49761821 ; 49831178
ChEBI ID
ChEBI:5855
CAS Number
15687-27-1
TTD Drug ID
D0R1QE
Formula
C13H18O2
Canonical SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
InChI
1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
InChIKey
HEFNNWSXXWATRW-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
1-hydroxyibuprofen DM004267
45117195
Oxidation - 1-hydroxylation 1 [8]
2-Hydroxyibuprofen DM004266
10443535
Oxidation - 2-hydroxylation 1 [9]
3-Hydroxyibuprofen DM004263
71312545
Oxidation - 3-hydroxylation 1 [9]
Ibuprofen glucuronide DM004265
163959
Conjugation - O-glucuronidation 1 [8] , [9]
Ibuprofen Metabolite M1 DM004254 N. A. Unclear 1 [2]
Carboxy-ibuprofen DM004264
10444113
Oxidation - Dehydrogenation 2 [8] , [9]
Ibuprofen Metabolite M2 DM004255 N. A. Unclear 2 [2]
Ibuprofen Metabolite M3 DM004256 N. A. Unclear 3 [2]
Ibuprofen Metabolite M4 DM004257 N. A. Unclear 4 [2]
Ibuprofen Metabolite M5 DM004258 N. A. Unclear 5 [2]
Ibuprofen Metabolite M6 DM004259 N. A. Unclear 6 [2]
Ibuprofen Metabolite M7 DM004260 N. A. Unclear 7 [2]
Ibuprofen Metabolite M8 DM004261 N. A. Unclear 8 [2]
Ibuprofen Metabolite M9 DM004262 N. A. Unclear 9 [2]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004632 Ibuprofen Ibuprofen Metabolite M1 Unclear ICL [2]
MR004641 Ibuprofen 3-Hydroxyibuprofen Oxidation - 3-hydroxylation CYP2C8 ... [9]
MR004643 Ibuprofen Ibuprofen glucuronide Conjugation - O-glucuronidation UGT1A1 ... [8], [9]
MR004644 Ibuprofen 2-Hydroxyibuprofen Oxidation - 2-hydroxylation CYP2C8 ... [9]
MR004645 Ibuprofen 1-hydroxyibuprofen Oxidation - 1-hydroxylation Unclear [8]
MR004642 3-Hydroxyibuprofen Carboxy-ibuprofen Oxidation - Dehydrogenation CYP2C9 [8], [9]
MR004633 Ibuprofen Metabolite M1 Ibuprofen Metabolite M2 Unclear ICD ... [2]
MR004634 Ibuprofen Metabolite M2 Ibuprofen Metabolite M3 Unclear CDO [2]
MR004635 Ibuprofen Metabolite M3 Ibuprofen Metabolite M4 Unclear HMSD [2]
MR004636 Ibuprofen Metabolite M4 Ibuprofen Metabolite M5 Unclear tam [2]
MR004637 Ibuprofen Metabolite M5 Ibuprofen Metabolite M6 Unclear dc [2]
MR004638 Ibuprofen Metabolite M6 Ibuprofen Metabolite M7 Unclear Unclear [2]
MR004639 Ibuprofen Metabolite M7 Ibuprofen Metabolite M8 Unclear ALDH [2]
MR004640 Ibuprofen Metabolite M8 Ibuprofen Metabolite M9 Unclear ACAD [2]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
4-Isobutylcatechol 2,3 dioxygenase (CDO) DMEN233 . Not Available Not Available [2]
5-isobutyl-2-hydroxymuconate semialdehy dehydrogenase (HMSD) DMEN234 . Not Available Not Available [2]
Acyl-CoA dehydrogenase (ACAD) DMEN239 Bacteroides fragilis Not Available Not Available [2]
Acyl-CoA thioesterase 2 (ACOT2) DME0255 Homo sapiens
ACOT2_HUMAN
3.1.2.2
[3]
Aldehyde dehydrogenase (ALDH) DMEN076 . Not Available Not Available [2]
Alpha-methylacyl-CoA racemase (AMACR) DME0116 Homo sapiens
AMACR_HUMAN
5.1.99.4
[4]
cis-1,2-dihydroxy-2-hydroibuprofenyl-CoA thiolase (ICT) DMEN232 . Not Available Not Available [2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
decarboxylase (dc) DMEN236 . Not Available Not Available [2]
Ibuprofenyl-CoA ligase (ICL) DMEN230 . Not Available Not Available [2]
lbuprofenyl-CoA 12 dioxygenase (ICD) DMEN231 . Not Available Not Available [2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
tautomerase (tam) DMEN235 . Not Available Not Available [2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8] , [9]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[8] , [9]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[9]
Unclear metabolic mechanism (DME-unclear) DME1464 Sphingomonas colocasiae Not Available Not Available [10]
⏷ Show the Full List of 21  DME(s)
References
1 Ibuprofen was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Genetic Characterization of the Ibuprofen-Degradative Pathway of Rhizorhabdus wittichii MPO218
3 A study on the chiral inversion of mandelic acid in humans. Org Biomol Chem. 2014 Sep 14;12(34):6737-44.
4 Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342.
5 Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87.
6 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
7 PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106.
8 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
9 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
10 Genetic and chemical characterization of ibuprofen degradation by Sphingomonas Ibu-2. Microbiology. 2013 Mar;159(Pt 3):621-632.

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