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

General Information of Drug (ID: DR0731)
Drug Name
Flurbiprofen sodium
Synonyms
Flubiprofen; Flugalin; Flurbiprofene; Flurbiprofene [INN-French]; Flurbiprofeno; Flurbiprofeno [INN-Spanish]; Flurbiprofenum; Flurbiprofenum [INN-Latin]; Flurofen; Froben; Stayban; U-27182; Zepolas; flurbiprofen; (+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid; 2-(2-fluorobiphenyl-4-yl)propanoic acid; 2-(3-fluoro-4-phenylphenyl)propanoic acid; 2-Fluoro-alpha-methyl-4-biphenylacetic acid; 3-Fluoro-4-phenylhydratropic acid; 5104-49-4; BTS 18322; BTS-18322; FP 70; Adfeed; Ansaid; Anside; Antadys; Cebutid; FLURBIPROFEN SODIUM; Flurbiprofen sodium [USP]; Flurbiprofen sodium salt; Sodium flurbiprofen; 2-Fluoro-alpha-methyl-4-diphenylacetic acid sodium salt; 56767-76-1; EINECS 260-373-2; Sodium 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate; Sodium 2-fluoro-alpha-methyl(1,1'-biphenyl)-4-acetate; Sodium 2-fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetate; Sodium 2-fluoro-alpha-methyl[1,1'-biphenyl]-4-acetate; Sodium 3-fluoro-4-phenylhydratropate; sodium 2-(2-fluorobiphenyl-4-yl)propanoate
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 266.24 Topological Polar Surface Area 40.1
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
23684814
CAS Number
56767-76-1
TTD Drug ID
D0A1PX
Formula
C15H12FNaO2
Canonical SMILES
CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)[O-].[Na+]
InChI
1S/C15H13FO2.Na/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11;/h2-10H,1H3,(H,17,18);/q;+1/p-1
InChIKey
AUAGTGKMTMVIKN-UHFFFAOYSA-M
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'-Hydroxyflurbiprofen DM004688
157678
Oxidation - 4'-hydroxylation 1 [4] , [6]
Flurbiprofen glucuronide DM004691
71316898
Conjugation - Glucuronidation 1 [5]
3',4'-dihydroxyflurbiprofen DM004689
128319
Unclear 2 [7]
3'-hydroxy-4'-methoxyflurbiprofen DM004690
128320
Unclear 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005041 Flurbiprofen sodium 4'-Hydroxyflurbiprofen Oxidation - 4'-hydroxylation CYP2C9 [4], [6]
MR005044 Flurbiprofen sodium Flurbiprofen glucuronide Conjugation - Glucuronidation UGT2B7 ... [5]
MR005042 4'-Hydroxyflurbiprofen 3',4'-dihydroxyflurbiprofen Unclear Unclear [7]
MR005043 3',4'-dihydroxyflurbiprofen 3'-hydroxy-4'-methoxyflurbiprofen Unclear Unclear [7]
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
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 6  DME(s)
References
1 Flurbiprofen Sodium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of CYP2C9 genetic polymorphism on the metabolism of flurbiprofen in vitro. Drug Dev Ind Pharm. 2015;41(8):1363-7.
3 Predominant contribution of UDP-glucuronosyltransferase 2B7 in the glucuronidation of racemic flurbiprofen in the human liver. Drug Metab Dispos. 2007 Jul;35(7):1182-7.
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 DrugBank(Pharmacology-Metabolism):Flurbiprofen
6 Comparative studies on the catalytic roles of cytochrome P450 2C9 and its Cys- and Leu-variants in the oxidation of warfarin, flurbiprofen, and diclofenac by human liver microsomes
7 Disposition of flurbiprofen in man: influence of stereochemistry and age

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