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

General Information of Drug (ID: DR0035)
Drug Name
Acemetacin
Prodrug Info Acemetacin is the prodrug of Indomethacin
Synonyms
Acemetacina; Acemetacina [INN-Spanish]; Acemetacine; Acemetacine [INN-French]; Acemetacinum; Acemetacinum [INN-Latin]; Acemix; Aximeixin; Emflex; Rantudil; Rheumibis; TVX 3322; indometacin carboxymethyl ester; indometacin glycolic ester; indomethacin carboxymethyl ester; indomethacin glycolic ester; 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, carboxymethyl ester; 53164-05-9; BRN 0501672; Bay f 4975; C21H18ClNO6; CHEBI:31162; CHEMBL189171; EINECS 258-403-4; K 708; K-708; UNII-5V141XK28X; acemetacin
Indication Osteoarthritis [ICD11: FA00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 415.8 Topological Polar Surface Area 94.8
Heavy Atom Count 29 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
1981
ChEBI ID
CHEBI:31162
CAS Number
53164-05-9
Formula
C21H18ClNO6
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/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)
InChIKey
FSQKKOOTNAMONP-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
Deacyl indomethacin DM000983
76151
Other reaction - N-Dehydroxylation; Hydrolysis 1 [3]
Indomethacin DM003065
3715
Hydrolysis - Esterase Hydrolysis 1 [3]
O-demethylatedacemetacin DM001521
21150398
Oxidation - O-Demethylation 1 [3]
O-desmethyl-des-4-chlorobenzoyl DM001524 N. A. Oxidation - Demethylation 1 [3]
Acemetacin-acyl-beta-D-glucuronide DM001522
129627227
Conjugation - Glucuronidation 2 [3]
Deacyl indomethacin glucuronide DM000985 N. A. Unclear 2 [3]
Des-p-chlorobenzoyl-O-desmethylindometacinsulfate DM001526 N. A. Unclear 2 [4]
Indometacin glycine DM001527 N. A. Unclear 2 [4]
O-desmethyl-des-4-chlorobenzoyl glucuronide DM001525 N. A. Conjugation - Glucuronidation 2 [3]
O-desmethylindometacinsulfate DM001523 N. A. Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000039 Acemetacin Deacyl indomethacin Other reaction - N-Dehydroxylation; Hydrolysis Unclear [3]
MR000040 Acemetacin O-demethylatedacemetacin Oxidation - O-Demethylation Unclear [3]
MR000041 Acemetacin O-desmethyl-des-4-chlorobenzoyl Oxidation - Demethylation Unclear [3]
MR000042 Acemetacin Indomethacin Hydrolysis - Esterase Hydrolysis ES [3]
MR000034 Deacyl indomethacin Deacyl indomethacin glucuronide Unclear UGT2B7 [3]
MR000043 Indomethacin Indometacin glycine Unclear Unclear [4]
MR000035 O-demethylatedacemetacin Acemetacin-acyl-beta-D-glucuronide Conjugation - Glucuronidation UGT2B7 [3]
MR000036 O-demethylatedacemetacin O-desmethylindometacinsulfate Unclear Unclear [5]
MR000037 O-desmethyl-des-4-chlorobenzoyl O-desmethyl-des-4-chlorobenzoyl glucuronide Conjugation - Glucuronidation UGT2B7 [3]
MR000038 O-desmethyl-des-4-chlorobenzoyl Des-p-chlorobenzoyl-O-desmethylindometacinsulfate Unclear UGT2B7 [4]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 National Center for Advancing Translational Science-Inxight: drug (5V141XK28X)
2 Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
3 DrugBank(Pharmacology-Metabolism)Acemetacin
4 [Comparative metabolic studies on [14C]-labelled acemetacin and indometacin in rats (author's transl)] Arzneimittelforschung. 1980;30(8A):1384-91.
5 U. S. FDA Label - Acemetacin

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