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

General Information of Drug (ID: DR0875)
Drug Name
Indomethacin
Synonyms
Idomethine; Imbrilon; Inacid; Indacin; Indo-Lemmon; Indo-rectolmin; Indo-tablinen; Indocid; Indocin; Indocin Sr; Indomecol; Indomed; Indomee; Indometacina; Indometacine; Indometacinum; Indometacyna; Indomethacine; Indomethacinum; Indomethazine; Indomethine; Indometicina; Indoptic; Indoptol; Indorektal; Inflazon; Infrocin; Inteban sp; Lausit; Metacen; Artracin; Artrinovo; Artrivia; Confortid; Dolcidium; Dolovin; Elmetacin; Metartril; Methazine; Metindol; Mezolin; Mikametan; Mobilan; Reumacide; Sadoreum; Tannex; indometacin; indomethacin; 53-86-1; Amuno
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 357.8 Topological Polar Surface Area 68.5
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3715
PubChem SID
5032 ; 611045 ; 612102 ; 832223 ; 841055 ; 856012 ; 3225554 ; 5208606 ; 6435989 ; 7847209 ; 7888379 ; 7979604 ; 8027945 ; 8027950 ; 8027958 ; 8149387 ; 8152346 ; 10321568 ; 10525985 ; 11111328 ; 11111329 ; 11113361 ; 11121750 ; 11122230 ; 11335446 ; 11360685 ; 11362903 ; 11363813 ; 11365465 ; 11366375 ; 11368027 ; 11368937 ; 11370997 ; 11370998 ; 11371496 ; 11373534 ; 11373628 ; 11376189 ; 11377099 ; 11404374 ; 11446060 ; 11461657 ; 11466300 ; 11467420 ; 11484715 ; 11486099 ; 11488786 ; 11490284 ; 11491833 ; 11494733
ChEBI ID
ChEBI:49662
CAS Number
53-86-1
TTD Drug ID
D0R1RS
Formula
C19H16ClNO4
Canonical SMILES
CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)OCC(=O)O
InChI
1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
InChIKey
CGIGDMFJXJATDK-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
5-hydroxyindomethacin DM000980
159665
Oxidation - O-Demethylation 1 [2]
Deacyl indomethacin DM000983
76151
Unclear 1 [2]
Indomethacin acyl glucuronide DM000986
70691027
Conjugation - O-Glucuronidation 1 [3] , [6]
5-hydroxyindomethacin glucuronide DM000981 N. A. Conjugation - Glucuronidation 2 [2]
5-hydroxyindomethacin sulfate DM000982 N. A. Conjugation - Sulfation 2 [2]
Deacyl indomethacin glucuronide DM000985 N. A. Conjugation - Glucuronidation 2 [2]
O-Desmethyl-N-deschlorobenzoyl indomethacin DM000984
11310252
Oxidation - O-Demethylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001200 Indomethacin 5-hydroxyindomethacin Oxidation - O-Demethylation CYP2C9 ... [2]
MR001201 Indomethacin Deacyl indomethacin Unclear CES1 [2]
MR001202 Indomethacin Indomethacin acyl glucuronide Conjugation - O-Glucuronidation UGT2B7 ... [3], [6]
MR001196 5-hydroxyindomethacin 5-hydroxyindomethacin glucuronide Conjugation - Glucuronidation UGT [2]
MR001197 5-hydroxyindomethacin 5-hydroxyindomethacin sulfate Conjugation - Sulfation SULT [2]
MR001198 Deacyl indomethacin O-Desmethyl-N-deschlorobenzoyl indomethacin Oxidation - O-Demethylation Unclear [2]
MR001199 Deacyl indomethacin Deacyl indomethacin glucuronide Conjugation - Glucuronidation UGT [2]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
⏷ Show the Full List of 15  DME(s)
References
1 Indomethacin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparative in vitro metabolism of phospho-tyrosol-indomethacin by mice, rats and humans Biochem Pharmacol. 2013 Apr 15;85(8):1195-202. doi: 10.1016/j.bcp.2013.01.031.
3 Contribution of UDP-glucuronosyltransferases 1A9 and 2B7 to the glucuronidation of indomethacin in the human liver. Eur J Clin Pharmacol. 2007 Mar;63(3):289-96.
4 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.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Herb-drug interaction in the protective effect of Alpinia officinarum against gastric injury induced by indomethacin based on pharmacokinetic, tissue distribution and excretion studies in rats. J Pharm Anal. 2021 Apr;11(2):200-209. doi: 10.1016/j.jpha.2020.05.009.

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