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

General Information of Drug (ID: DR0666)
Drug Name
Etodolac
Synonyms
Edolan; Etodolaco; Etodolaco [INN-Spanish]; Etodolacum; Etodolacum [INN-Latin]; Etodolic acid; Lodine; Lodine XL; N-Methyl Etodolac; Ramodar; Ultradol; etodolac; 1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid; 1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid; 1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid; 2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid; 41340-25-4; AY 24236; AY-24,236; AY-24236; CCRIS 3923; CHEMBL622; NSC 282126
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 287.35 Topological Polar Surface Area 62.3
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3308
PubChem SID
9204 ; 143623 ; 224459 ; 855612 ; 5268437 ; 7847381 ; 7979205 ; 8149693 ; 8152106 ; 10321309 ; 11335322 ; 11360561 ; 11364138 ; 11366700 ; 11369262 ; 11372457 ; 11373819 ; 11377424 ; 11461533 ; 11466259 ; 11467379 ; 11485110 ; 11485958 ; 11489203 ; 11491244 ; 11492225 ; 11495058 ; 12012673 ; 14824710 ; 17405042 ; 24278407 ; 26612147 ; 26680024 ; 26747213 ; 26747214 ; 29222445 ; 46505184 ; 47885271 ; 47959585 ; 47959586 ; 48034967 ; 48110316 ; 48184861 ; 48259079 ; 48334348 ; 48413770 ; 49698757 ; 49857374 ; 50105240 ; 50105241
ChEBI ID
CHEBI:4909
CAS Number
41340-25-4
TTD Drug ID
D0N1WU
Formula
C17H21NO3
Canonical SMILES
CCC1=C2C(=CC=C1)C3=C(N2)C(OCC3)(CC)CC(=O)O
InChI
1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
InChIKey
NNYBQONXHNTVIJ-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
4-ureido-etodolac DM000939 N. A. Unclear 1 [5]
6-hydroxyetodolac DM000936
14146232
Oxidation - 6-Hydroxylation 1 [6]
7-hydroxyetodolac DM000934
14112821
Oxidation - 7-Hydroxylation 1 [6]
8-(1-hydroxyethyl)etodolac DM000937
14146249
Oxidation - Hydroxylation 1 [5]
Etodolac acyl glucuronide DM000938
131769991
Conjugation - Glucuronidation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002734 Etodolac 7-hydroxyetodolac Oxidation - 7-Hydroxylation CYP2C9 [6]
MR002735 Etodolac 6-hydroxyetodolac Oxidation - 6-Hydroxylation CYP2C9 [6]
MR002736 Etodolac 8-(1-hydroxyethyl)etodolac Oxidation - Hydroxylation CYP2C9 [5]
MR002737 Etodolac Etodolac acyl glucuronide Conjugation - Glucuronidation UGT1A3 ... [6]
MR002738 Etodolac 4-ureido-etodolac Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_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 [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 12  DME(s)
References
1 Propranolol Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Stereoselective glucuronidation and hydroxylation of etodolac by UGT1A9 and CYP2C9 in man. Xenobiotica. 2004 May;34(5):449-61.
3 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.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Etodolac clinical pharmacokinetics
6 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. doi: 10.2174/092986709789057635.

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