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

General Information of Drug (ID: DR1014)
Drug Name
Mefenamic acid
Synonyms
Mefacit; Mefanamic acid; Mefedolo; Mefenacid; Mefenaminsaeure; Mephenamic acid; Mephenaminic acid; Methenamic acid; Mycasaal; Acide mefenamique; Acido mefenamico; Acidum mefenamicum; Bafameritin-M; Bafhameritin-M; Bonabol; CN-35355; Coslan; Lysalgo; N-(2,3-Xylyl)anthranilic acid; N-2,3-Xylylanthranilic acid; Namphen; Parkemed; Ponalar; Ponstan; Ponstan forte; Ponstel; Ponstil; Ponstyl; Pontal; Tamany Bonsan; Tanston; Vialidon; mefenamic acid; 2-((2,3-Dimethylphenyl)amino)benzoic acid; 2-[(2,3-dimethylphenyl)amino]benzoic acid; 61-68-7; HL 1
Indication Female pelvic pain [ICD11: GA34] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 241.28 Topological Polar Surface Area 49.3
Heavy Atom Count 18 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4044
PubChem SID
5243 ; 399652 ; 798379 ; 840129 ; 855723 ; 4906250 ; 7847219 ; 7872085 ; 7979881 ; 8149703 ; 8152534 ; 10321491 ; 10530006 ; 11112163 ; 11335473 ; 11360712 ; 11363068 ; 11365630 ; 11368192 ; 11372043 ; 11374868 ; 11376354 ; 11461684 ; 11466082 ; 11467202 ; 11485737 ; 11485864 ; 11489757 ; 11490897 ; 11493049 ; 11493988 ; 14847469 ; 24424559 ; 24715034 ; 24896815 ; 26512268 ; 26612162 ; 26679725 ; 26746974 ; 26746975 ; 26751493 ; 29223155 ; 46505405 ; 47365092 ; 47440151 ; 47440152 ; 47662184 ; 47662185 ; 48035004 ; 48184900
ChEBI ID
CHEBI:6717
CAS Number
61-68-7
TTD Drug ID
D05FTJ
Formula
C15H15NO2
Canonical SMILES
CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C
InChI
1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
InChIKey
HYYBABOKPJLUIN-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
3-hydroxymethyl Mefenamic Acid DM001080
610738
Oxidation - Hydroxylation 1 [4]
Mefenamic acyl-beta-D-glucuronide DM001092
128135
Conjugation - N-Glucuronidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001630 Mefenamic acid 3-hydroxymethyl Mefenamic Acid Oxidation - Hydroxylation CYP2C9 [4]
MR001631 Mefenamic acid Mefenamic acyl-beta-D-glucuronide Conjugation - N-Glucuronidation CYP2C8 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
References
1 Mefenamic Acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Both reactivity and accessibility are important in cytochrome P450 metabolism: a combined DFT and MD study of fenamic acids in BM3 mutants. J Chem Inf Model. 2019 Feb 25;59(2):743-753.
3 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
4 Cytochrome P450-mediated bioactivation of mefenamic acid to quinoneimine intermediates and inactivation by human glutathione S-transferases. Chem Res Toxicol. 2014 Dec 15;27(12):2071-81.

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