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

General Information of Drug (ID: DR2700)
Drug Name
Indomethacin glucuronide
Synonyms Indomethacin acyl glucuronide; INDOMETHACIN GLUCURONIDE; CHEMBL2074828; Indomethacin Acyl-; INDOMETHACIN ACYL-B-D-GLUCURONIDE; 75523-11-4; ZINC84386263
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 533.9 Topological Polar Surface Area 165
Heavy Atom Count 37 Rotatable Bond Count 7
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
70691027
CAS Number
75523-11-4
Formula
C25H24ClNO10
Canonical SMILES
CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)OC4C(C(C(C(O4)C(=O)O)O)O)O
InChI
1S/C25H24ClNO10/c1-11-15(10-18(28)36-25-21(31)19(29)20(30)22(37-25)24(33)34)16-9-14(35-2)7-8-17(16)27(11)23(32)12-3-5-13(26)6-4-12/h3-9,19-22,25,29-31H,10H2,1-2H3,(H,33,34)/t19-,20-,21+,22-,25+/m0/s1
InChIKey
QCBWEVBGELGABM-CZLVRFMKSA-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
N-deschlorobenzoyl-indometha acyl glucuronide DM004236 N. A. Unclear 1 [4]
O-desmethy-indomethacin-acyl glucuronlde DM004235 N. A. Unclear 1 [4]
N-deschlorobenzoyl-indometha acyl glucuronide DM004236 N. A. Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004629 Indomethacin glucuronide O-desmethy-indomethacin-acyl glucuronlde Unclear Unclear [4]
MR004631 Indomethacin glucuronide N-deschlorobenzoyl-indometha acyl glucuronide Unclear Unclear [4]
MR004630 O-desmethy-indomethacin-acyl glucuronlde N-deschlorobenzoyl-indometha acyl glucuronide Unclear Unclear [4]
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]
Beta-glucuronidase (uidA) DME1830 Erysipelatoclostridium ramosum
BGLR_ECOLI
3.2.1.31
[3]
Beta-glucuronidase (uidA) DME1846 Bacteroides vulgatus
A0A174N6T8_BACVU
3.2.1.31
[3]
Beta-glucuronidase (uidA) DME1935 Roseburia hominis
A0A395VBK3_9FIRM
3.2.1.31
[3]
Beta-glucuronidase (uidA) DME1937 Roseburia intestinalis
A0A173S9G2_9FIRM
3.2.1.31
[3]
References
1 Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol. Int J Pharm. 2010 Jan 4;383(1-2):24-9.
2 Bidirectional interactions between indomethacin and the murine intestinal microbiota. Elife. 2015 Dec 23;4:e08973.
3 Developing a metagenomic view of xenobiotic metabolism. Pharmacol Res. 2013 Mar;69(1):21-31.
4 Determination of indomethacin, its metabolites and their glucuronides in human plasma and urine by means of direct gradient high-performance liquid chromatographic analysis. Preliminary pharmacokinetics and effect of probenecid

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