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

General Information of Drug (ID: DR1160)
Drug Name
Nimesulide
Synonyms
Nimesulida [INN-Spanish]; Nimesulidum [INN-Latin]; Nisulid; Sulidene; V4TKW1454M; nimesulide; 4'-Nitro-2'-phenoxymethanesulfonanilide; Flogovital; Mesulid; 4'-Nitro-2'-phenoxymethansulfonanilid; 4-NITRO-2-PHENOXYMETHANESULFONANILIDE; 4-Nitro-2-phenoxy-methanesulfonanilide; 51803-78-2; BRN 2421175; CHEBI:44445; CHEMBL56367; EINECS 257-431-4; MLS000069680; Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)-; Methanesulfonanilide, 4'-nitro-2'-phenoxy-; N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide; Nimed; R 805; R-805; UNII-V4TKW1454M
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 308.31 Topological Polar Surface Area 110
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
4495
PubChem SID
855635 ; 5912186 ; 6436673 ; 7404099 ; 7848112 ; 7889413 ; 7980127 ; 8149946 ; 8152768 ; 10321585 ; 11111520 ; 11111521 ; 11121727 ; 11122207 ; 11335868 ; 11361107 ; 11362857 ; 11364471 ; 11365419 ; 11367033 ; 11367981 ; 11369595 ; 11370925 ; 11370926 ; 11372711 ; 11373582 ; 11373834 ; 11376143 ; 11377757 ; 11462079 ; 11466222 ; 11467342 ; 11485118 ; 11485804 ; 11489357 ; 11491391 ; 11491993 ; 11495391 ; 12012650 ; 14752054 ; 17405416 ; 24277576 ; 24278583 ; 26612437 ; 26680139 ; 26697157 ; 26746940 ; 26746941 ; 26751468 ; 29215000
ChEBI ID
CHEBI:44445
CAS Number
51803-78-2
TTD Drug ID
D0C0JT
Formula
C13H12N2O5S
Canonical SMILES
CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2
InChI
1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
InChIKey
HYWYRSMBCFDLJT-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-hydroxynimesulideM1 DM002714
130995
Unclear 1 [3]
Nimesulide metabolite M2 DM002716 N. A. Unclear 2 [3]
Nimesulide metabolite M5A,5B DM002715
11822507
Unclear 2 [3]
Nimesulide metabolite M2 DM002716 N. A. Unclear 3 [3]
Nimesulide metabolite M3 DM002717 N. A. Unclear 3 [3]
Nimesulide metabolite M5C DM002722
10902415
Unclear 3 [3]
Nimesulide metabolite M7 DM002721 N. A. Unclear 3 [3]
Nimesulide metabolite M8 DM003047 N. A. Unclear 3 [3]
Nimesulide metabolite M9 DM002719 N. A. Unclear 3 [3]
Nimesulide metabolite M3 DM002717 N. A. Unclear 4 [3]
Nimesulide metabolite M4 DM002718 N. A. Unclear 4 [3]
Nimesulide metabolite M6 DM002720 N. A. Unclear 4 [3]
Nimesulide metabolite M4 DM002718 N. A. Unclear 5 [3]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003328 Nimesulide 4-hydroxynimesulideM1 Unclear Unclear [3]
MR003318 4-hydroxynimesulideM1 Nimesulide metabolite M5A,5B Unclear Unclear [3]
MR003319 4-hydroxynimesulideM1 Nimesulide metabolite M2 Unclear CYP2C19 ... [3]
MR003320 Nimesulide metabolite M5A,5B Nimesulide metabolite M2 Unclear Unclear [3]
MR003321 Nimesulide metabolite M5A,5B Nimesulide metabolite M9 Unclear Unclear [3]
MR003322 Nimesulide metabolite M5A,5B Nimesulide metabolite M7 Unclear Unclear [3]
MR003323 Nimesulide metabolite M5A,5B Nimesulide metabolite M5C Unclear Unclear [3]
MR003324 Nimesulide metabolite M5A,5B Nimesulide metabolite M8 Unclear Unclear [3]
MR003325 Nimesulide metabolite M2 Nimesulide metabolite M3 Unclear RSH [3]
MR003327 Nimesulide metabolite M9 Nimesulide metabolite M6 Unclear Unclear [3]
MR003326 Nimesulide metabolite M3 Nimesulide metabolite M4 Unclear Unclear [3]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 An investigation into drug products withdrawn from the EU market between 2002 and 2011 for safety reasons and the evidence used to support the decision-making. BMJ Open. 2014 Jan 15;4(1):e004221.
2 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
3 Neutrophil- and myeloperoxidase-mediated metabolism of reduced nimesulide: evidence for bioactivation Chem Res Toxicol. 2010 Nov 15;23(11):1691-700. doi: 10.1021/tx1001496.

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