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

General Information of Drug (ID: DR2890)
Drug Name
Ketoprofen glucuronide
Synonyms
Ketoprofen glucuronide; KETOPROFEN ACYL-B-D-GLUCURONIDE; 76690-94-3; DL-Ketoprofen glucuronide; (R)-Ketoprofen Glucuronide; (S)-Ketoprofen Glucuronide; CHEMBL3526739; DTXSID30998002; FT-0670648; W-203754; 1-O-[2-(3-Benzoylphenyl)propanoyl]hexopyranuronic acid; 1-(3-benzoyl-alpha-methylbenzeneacetate) beta-D-glucopyranuronic acid; beta-D-Glucopyranuronic acid, 1-(3-benzoyl-alpha-methylbenzeneacetate); 1-(3-benzoyl-alpha-methylbenzeneacetate) beta-delta-glucopyranuronic acid
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 430.4 Topological Polar Surface Area 151
Heavy Atom Count 31 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
131281
CAS Number
76690-94-3
Formula
C22H22O9
Canonical SMILES
CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)OC3C(C(C(C(O3)C(=O)O)O)O)O
InChI
1S/C22H22O9/c1-11(13-8-5-9-14(10-13)15(23)12-6-3-2-4-7-12)21(29)31-22-18(26)16(24)17(25)19(30-22)20(27)28/h2-11,16-19,22,24-26H,1H3,(H,27,28)/t11?,16-,17-,18+,19-,22-/m0/s1
InChIKey
PBTXSZZKPHBHMA-LYFYOZKASA-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
Ketoprofen glucuronide Metabolite M1 DM004204 N. A. Hydrolysis - Hydrolysis 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004595 Ketoprofen glucuronide Ketoprofen glucuronide Metabolite M1 Hydrolysis - Hydrolysis OXA1L [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-glucuronidase (uidA) DME1788 Escherichia coli
BGLR_ECOLI
3.2.1.31
[2]
Mitochondrial inner membrane protein OXA1L (OXA1L) DMEN224 Homo sapiens
OXA1L_HUMAN
Not Available [3]
References
1 Stereoselective pharmacokinetics of ketoprofen and ketoprofen glucuronide in end-stage renal disease: evidence for a 'futile cycle' of elimination. Br J Clin Pharmacol. 1999 Oct;48(4):494-500.
2 Bacterial beta-glucuronidase inhibition protects mice against enteropathy induced by indomethacin, ketoprofen or diclofenac: mode of action and pharmacokinetics. Xenobiotica. 2014 Jan;44(1):28-35.
3 Stereoselective esterase activity of human serum albumin toward ketoprofen glucuronide

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