General Information of Drug (ID: DR1914)
Drug Name
Imrecoxib
Synonyms
Imrecoxib; Imricoxib; LS-194053; SCHEMBL3034253; SGW6W5758V; 2H-Pyrrol-2-one, 1,5-dihydro-3-(4-methylphenyl)-4-(4-(methylsulfonyl)phenyl)-1-propyl-; BAP-909; 395683-14-4; BDBM50293282; CHEMBL504535; CS-0079499; DB12354; HY-114200; UNII-SGW6W5758V
Indication Osteoarthritis [ICD11: FA00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 369.5 Topological Polar Surface Area 62.8
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
11682175
ChEBI ID
CHEBI:68602
CAS Number
395683-14-4
TTD Drug ID
D0AL8M
Formula
C21H23NO3S
Canonical SMILES
CCCN1CC(=C(C1=O)C2=CC=C(C=C2)C)C3=CC=C(C=C3)S(=O)(=O)C
InChI
1S/C21H23NO3S/c1-4-13-22-14-19(16-9-11-18(12-10-16)26(3,24)25)20(21(22)23)17-7-5-15(2)6-8-17/h5-12H,4,13-14H2,1-3H3
InChIKey
AXMZZGKKZDJGAZ-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
Imrecoxib metabolite M1 DM002564 N. A. Unclear 1 [3] , [4]
Imrecoxib metabolite M4 DM002559
2526194
Oxidation - Oxidation 1 [5]
Imrecoxib metabolite M1 DM002564 N. A. Oxidation - Oxidation 2 [6]
Imrecoxib metabolite M2 DM002560
156613689
Unclear 2 [3] , [4]
Imrecoxib metabolite M2 DM002560
156613689
Oxidation - Oxidation 2 [5]
Imrecoxib metabolite M3 DM002562 N. A. Oxidation - Hydroxylation 2 [7]
Imrecoxib metabolite M6 DM002561 N. A. Conjugation - Glucuronidation 3 [8]
Imrecoxib metabolite M7 DM002563 N. A. Conjugation - Glucuronidation 3 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001174 Imrecoxib Imrecoxib metabolite M4 Oxidation - Oxidation Unclear [5]
MR001175 Imrecoxib Imrecoxib metabolite M1 Unclear CYP2D6 ... [3], [4]
MR001173 Imrecoxib metabolite M1 Imrecoxib metabolite M2 Unclear CYP2D6 ... [3], [4]
MR001168 Imrecoxib metabolite M4 Imrecoxib metabolite M2 Oxidation - Oxidation Unclear [5]
MR001169 Imrecoxib metabolite M4 Imrecoxib metabolite M3 Oxidation - Hydroxylation Unclear [7]
MR001170 Imrecoxib metabolite M4 Imrecoxib metabolite M1 Oxidation - Oxidation Unclear [6]
MR001171 Imrecoxib metabolite M2 Imrecoxib metabolite M6 Conjugation - Glucuronidation Unclear [8]
MR001172 Imrecoxib metabolite M3 Imrecoxib metabolite M7 Conjugation - Glucuronidation Unclear [9]
⏷ Show the Full List of 8 MR(s)
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]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 ClinicalTrials.gov (NCT01985165) A Phase 4 Study of Imrecoxib in Treatment of Knee Osteoarthritis.
2 Lack of effect of Imrecoxib, an innovative and moderate COX-2 inhibitor, on pharmacokinetics and pharmacodynamics of warfarin in healthy volunteers. Sci Rep. 2019 Oct 31;9(1):15774.
3 Differences in the In Vivo and In Vitro Metabolism of Imrecoxib in Humans: Formation of the Rate-Limiting Aldehyde Intermediate Drug Metab Dispos. 2018 Sep;46(9):1320-1328. doi: 10.1124/dmd.118.081182.
4 Comparative Pharmacokinetics and Safety of Imrecoxib, a Novel Selective Cyclooxygenase-2 Inhibitor, in Elderly Healthy Subjects. Drug Des Devel Ther. 2022 Nov 8;16:3865-3876. doi: 10.2147/DDDT.S387508.
5 Metabolism and excretion of imrecoxib in rat Xenobiotica. 2006 May;36(5):441-55. doi: 10.1080/00498250600595524.
6 Exposures to estradiol, ethinylestradiol and octylphenol affect survival and growth of Rana pipiens and Rana sylvatica tadpoles J Toxicol Environ Health A. 2006 Aug;69(16):1555-69. doi: 10.1080/15287390500470759.
7 Database composition can affect the structure-activity relationship prediction J Toxicol Environ Health A. 2006 Aug;69(16):1527-40. doi: 10.1080/15287390500468746.
8 Ozone exposure impairs antigen-specific immunity but activates IL-7-induced proliferation of CD4-CD8- thymocytes in BALB/c mice J Toxicol Environ Health A. 2006 Aug;69(16):1511-26. doi: 10.1080/15287390500468696.
9 Changes in the growth, but not the survival, of American kestrels (Falco sparverius) exposed to environmentally relevant polybrominated diphenyl ethers J Toxicol Environ Health A. 2006 Aug;69(16):1541-54. doi: 10.1080/15287390500468753.

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