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

General Information of Drug (ID: DR2291)
Drug Name
Meclofenamic acid
Synonyms
Meclofenamate; Meclofenamic acid (USAN/INN); Meclofenamic acid [USAN:INN:BAN]; Meclomen (free acid); Meclophenamic acid; 2-((2,6-Dichloro-3-methylphenyl)amino)benzoic acid; 2-(2,6-Dichloro-3-methylphenyl)aminobenzoic acid; Acide meclofenamique; Acide meclofenamique [INN-French]; Acido meclofenamico; Acido meclofenamico [INN-Spanish]; Acidum meclofenamicum; Acidum meclofenamicum [INN-Latin]; Arquel; INF 4668; INF-4668; 2-(2,6-dichloro-3-methylanilino)benzoic acid; 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid; CL 583; N-(2,6-Dichloro-3-methylphenyl)anthranilic acid; N-(2,6-Dichloro-m-tolyl)anthranilic acid; N-(3-Methyl-2,6-dichlorophenyl)anthranilic acid
Indication Myalgia [ICD11: FB56] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.1 Topological Polar Surface Area 49.3
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4037
PubChem SID
9328 ; 400193 ; 840128 ; 7457972 ; 7849400 ; 7979877 ; 8152527 ; 11335679 ; 11360918 ; 11363787 ; 11366349 ; 11368911 ; 11371551 ; 11373614 ; 11377073 ; 11461890 ; 11466234 ; 11467354 ; 11484706 ; 11485848 ; 11488861 ; 11490302 ; 11491853 ; 11494707 ; 14800267 ; 24424562 ; 29223148 ; 46507887 ; 47365144 ; 47440206 ; 47588953 ; 47662236 ; 47959696 ; 48110417 ; 48110418 ; 48334447 ; 49846785 ; 49870448 ; 50103859 ; 50264248 ; 53788368 ; 57322106 ; 85173910 ; 85788470 ; 85789196 ; 103173431 ; 103828114 ; 104305246 ; 117467594 ; 118313497
ChEBI ID
CHEBI:6710
CAS Number
644-62-2
TTD Drug ID
D08IFL
Formula
C14H11Cl2NO2
Canonical SMILES
CC1=C(C(=C(C=C1)Cl)NC2=CC=CC=C2C(=O)O)Cl
InChI
1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)
InChIKey
SBDNJUWAMKYJOX-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]
3-hydroxymethyl Mefenamic Acid DM001080
610738
Oxidation - Hydroxylation 1 [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001613 Meclofenamic acid 3-hydroxymethyl Mefenamic Acid Oxidation - Hydroxylation cyp102A1 [2], [4]
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 102D1 (cyp102) DME1465 Streptomyces avermitilis
CPXB_BACMB
1.14.14.1
[3]
Vitamin D3 dihydroxylase (cyp105A1) DMEN027 Streptomyces griseolus
CPXE_STRGO
Not Available [4]
References
1 Meclofenamic 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 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. doi: 10.1021/acs.jcim.8b00750.
4 Metabolism of non-steroidal anti-inflammatory drugs (NSAIDs) by Streptomyces griseolus CYP105A1 and its variants Drug Metab Pharmacokinet. 2022 Aug;45:100455. doi: 10.1016/j.dmpk.2022.100455.

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