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

General Information of Drug (ID: DR0286)
Drug Name
Celecoxib
Synonyms
Celebra; Celebrex; Celecox; Celecoxibum; Celocoxib; JCX84Q7J1L; Onsenal; SC 58635; SC-58635; SC58635; YM 177; YM-177; celecoxib; 169590-42-5; 184007-95-2; 4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide; 4-[5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE; 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide; C17H14F3N3O2S; CHEMBL118; HSDB 7038; MFCD00941298; UNII-JCX84Q7J1L; YM177; p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 381.4 Topological Polar Surface Area 86.4
Heavy Atom Count 26 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
2662
PubChem SID
9791 ; 535138 ; 828874 ; 841958 ; 5364750 ; 7847633 ; 7886547 ; 7978890 ; 8150033 ; 8151729 ; 11336068 ; 11361307 ; 11363326 ; 11364763 ; 11365888 ; 11367325 ; 11368450 ; 11369887 ; 11372927 ; 11373130 ; 11373862 ; 11375487 ; 11376612 ; 11378052 ; 11445401 ; 11462279 ; 11485248 ; 11489392 ; 11491811 ; 11491997 ; 11494246 ; 11528618 ; 12015009 ; 14755918 ; 17389545 ; 26612517 ; 26680503 ; 26697316 ; 26747363 ; 26747364 ; 29221820 ; 46392808 ; 46505596 ; 46512162 ; 47365253 ; 47589055 ; 47959816 ; 48110506 ; 48413391 ; 48415737
ChEBI ID
ChEBI:41423
CAS Number
169590-42-5
TTD Drug ID
D03RTS
Formula
C17H14F3N3O2S
Canonical SMILES
CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
InChI
1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChIKey
RZEKVGVHFLEQIL-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
Celecoxib glucuronide DM000755
10415951
Conjugation - Glucuronidation 1 [3]
Hydroxycelecoxib DM000753
9908776
Oxidation - Hydroxylation 1 [3]
Carboxycelecoxib DM000754
10047220
Unclear 2 [3]
Celecoxib glucuronide DM000755
10415951
Conjugation - Glucuronidation 3 [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000587 Celecoxib Hydroxycelecoxib Oxidation - Hydroxylation CYP2C9 ... [3]
MR000588 Celecoxib Celecoxib glucuronide Conjugation - Glucuronidation UGT [3]
MR000585 Hydroxycelecoxib Carboxycelecoxib Unclear ADH1A ... [3]
MR000586 Carboxycelecoxib Celecoxib metabolite M1 Conjugation - Glucuronidation UGT [10]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alcohol dehydrogenase (quinone), cytochrome c subunit (adhB) DMEN018 Gluconobacter oxydans
ADHB_GLUOX
Not Available [2]
Alcohol dehydrogenase class-I alpha (ADH1A) DME0127 Homo sapiens
ADH1A_HUMAN
1.1.1.1
[2]
Alcohol dehydrogenase class-I beta (ADH1B) DME0128 Homo sapiens
ADH1B_HUMAN
1.1.1.105
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[8]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [9]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [9]
⏷ Show the Full List of 10  DME(s)
References
1 Celecoxib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Celecoxib pathways: pharmacokinetics and pharmacodynamics Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb.
3 Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8.
4 Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510.
5 Drug interactions in dentistry: the importance of knowing your CYPs. J Am Dent Assoc. 2004 Mar;135(3):298-311.
6 Celecoxib is a substrate of CYP2D6: impact on celecoxib metabolism in individuals with CYP2C9*3 variants. Drug Metab Pharmacokinet. 2018 Oct;33(5):219-227.
7 Major role of human liver microsomal cytochrome P450 2C9 (CYP2C9) in the oxidative metabolism of celecoxib, a novel cyclooxygenase-II inhibitor. J Pharmacol Exp Ther. 2000 May;293(2):453-9.
8 Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus. Aquat Toxicol. 2007 Mar 10;81(3):286-92.
9 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
10 Quantitation of celecoxib and four of its metabolites in rat blood by UPLC-MS/MS clarifies their blood distribution patterns and provides more accurate pharmacokinetics profiles J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Sep 15;1001:202-11. doi: 10.1016/j.jchromb.2015.07.026.

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