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

General Information of Drug (ID: DR0907)
Drug Name
Ketoprofen
Synonyms
Kefenid; Ketoprofene; Ketoprofeno; Ketoprofenum [INN-Latin]; Ketopron; Ketoprophene; Lertus; Menamin; Meprofen; Orudis; Orudis (TN); Orudis KT; Orugesic; Oruvail; Oscorel; Profenid; RP 19583; RP-19583; Toprec; Toprek; ketoprofen; m-Benzoylhydratropic acid; Actron; Alrheumat; Alrheumun; Capisten; Epatec; Fastum; racemic-Ketoprofen; 2-(3-Benzoylphenyl)propanoic acid; 2-(3-Benzoylphenyl)propionic acid; 2-(m-Benzoylphenyl)propionic acid; 2-[3-(phenylcarbonyl)phenyl]propanoic acid; 22071-15-4; 3-Benzoylhydratropic acid; Aneol; Dexal; Iso-K
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 254.28 Topological Polar Surface Area 54.4
Heavy Atom Count 19 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3825
PubChem SID
4853 ; 857801 ; 5316933 ; 7847200 ; 7979680 ; 8149782 ; 8152423 ; 10321584 ; 10513923 ; 11335773 ; 11361012 ; 11364203 ; 11366765 ; 11369327 ; 11372636 ; 11373574 ; 11377489 ; 11461984 ; 11466247 ; 11467367 ; 11484688 ; 11485894 ; 11488772 ; 11491294 ; 11491843 ; 11495123 ; 11532908 ; 11533518 ; 15122326 ; 17405247 ; 24278504 ; 24860779 ; 24896217 ; 26612243 ; 26679814 ; 26747548 ; 26747549 ; 29222944 ; 46505715 ; 47216761 ; 47365167 ; 47588981 ; 47588982 ; 47588983 ; 47662267 ; 47736456 ; 47810738 ; 48184977 ; 48413934 ; 49698784
ChEBI ID
ChEBI:6128
CAS Number
22071-15-4
TTD Drug ID
D0W9WF
Formula
C16H14O3
Canonical SMILES
CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
InChI
1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
InChIKey
DKYWVDODHFEZIM-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
2-[3-(4-hydroxybenzoyl) phenyl]-propanoic acid DM002812
3031176
Oxidation - Hydroxylation 1 [3] , [5]
2-[3-(hydroxy(phenyl)methyl) phenyl]-propanoic acid DM002818
11817710
Oxidation - Hydroxylation 1 [3] , [5]
3-Hydroxy ketoprofen DM002815
10659648
Oxidation - Hydroxylation 1 [3] , [5]
Ketoprofen glucuronide DM003109
131281
Conjugation - Glucuronidation 1 [5]
Ketoprofen metabolite 1 DM002813 N. A. Conjugation - Glucuronidation 2 [3] , [5]
Ketoprofen metabolite 2 DM002816 N. A. Conjugation - Glucuronidation 2 [3] , [5]
Ketoprofen metabolite 3 DM002814 N. A. Conjugation - Glucuronidation 2 [3] , [5]
Ketoprofen metabolite 4 DM002817 N. A. Conjugation - Glucuronidation 2 [3] , [5]
Ketoprofen metabolite 5 DM002819 N. A. Conjugation - Glucuronidation 2 [3] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001363 Ketoprofen 2-[3-(4-hydroxybenzoyl) phenyl]-propanoic acid Oxidation - Hydroxylation CYP2C8 ... [3], [5]
MR001364 Ketoprofen 2-[3-(3-hydroxybenzoyl) phenyl]-propanoic acid Oxidation - Hydroxylation CYP2C8 ... [3], [5]
MR001365 Ketoprofen 2-[3-(hydroxy(phenyl)methyl) phenyl]-propanoic acid Oxidation - Hydroxylation CYP2C8 ... [3], [5]
MR001366 Ketoprofen Ketoprofen glucuronide Conjugation - Glucuronidation Unclear [5]
MR001360 2-[3-(3-hydroxybenzoyl) phenyl]-propanoic acid Ketoprofen metabolite 2 Conjugation - Glucuronidation Unclear [3], [5]
MR001361 2-[3-(3-hydroxybenzoyl) phenyl]-propanoic acid Ketoprofen metabolite 4 Conjugation - Glucuronidation Unclear [3], [5]
MR001358 2-[3-(4-hydroxybenzoyl) phenyl]-propanoic acid Ketoprofen metabolite 1 Conjugation - Glucuronidation Unclear [3], [5]
MR001359 2-[3-(4-hydroxybenzoyl) phenyl]-propanoic acid Ketoprofen metabolite 3 Conjugation - Glucuronidation Unclear [3], [5]
MR001362 2-[3-(hydroxy(phenyl)methyl) phenyl]-propanoic acid Ketoprofen metabolite 5 Conjugation - Glucuronidation Unclear [3], [5]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
References
1 Ketoprofen was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis Eur J Drug Metab Pharmacokinet. 2011 Sep;36(3):167-73. doi: 10.1007/s13318-011-0041-1.
3 Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis. Eur J Drug Metab Pharmacokinet. 2011 Sep;36(3):167-73.
4 Association between the UGT1A1*28 allele and hyperbilirubinemia in HIV-positive patients receiving atazanavir: a meta-analysis. Biosci Rep. 2019 May 2;39(5). pii: BSR20182105.
5 Characterization and quantification of metabolites of racemic ketoprofen excreted in urine following oral administration to man by 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism Xenobiotica. 2004 Nov-Dec;34(11-12):1075-89. doi: 10.1080/00498250412331281098.

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