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

General Information of Drug (ID: DR1300)
Drug Name
Piroxicam
Synonyms
Pirkam; Piroflex; Piroftal; Piroxicam (Feldene); Piroxicamum; Piroxicamum [INN-Latin]; Pyroxycam; Reudene; Riacen; Roxicam; Roxiden; Sasulen; Solocalm; Artroxicam; Bruxicam; CHF 1251; Caliment; Erazon; Feldene; Flogobene; Geldene; Improntal; Larapam; Zunden; piroxicam; piroxicam usp; 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide; 36322-90-4; 4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide; BAXO; CCRIS 3719; CP 16171; CP-16171; NSC 666076; Roxam; UNII-13T4O6VMAM
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 331.3 Topological Polar Surface Area 108
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
54676228
PubChem SID
4761 ; 511550 ; 627224 ; 856007 ; 859011 ; 3248708 ; 5005569 ; 7847195 ; 7980333 ; 8149487 ; 10321546 ; 10520247 ; 10591135 ; 11111641 ; 11111642 ; 11113322 ; 11120243 ; 11120731 ; 11121219 ; 11121700 ; 11122180 ; 11335544 ; 11360783 ; 11362784 ; 11364009 ; 11365346 ; 11366571 ; 11367908 ; 11369133 ; 11370819 ; 11370820 ; 11371780 ; 11373509 ; 11374454 ; 11376070 ; 11377295 ; 11427267 ; 11461755 ; 11466239 ; 11467359 ; 11485029 ; 11485878 ; 11489103 ; 11490596 ; 11492783 ; 11494929 ; 12013846 ; 14924343 ; 17405458 ; 24583179
ChEBI ID
ChEBI:8249
CAS Number
36322-90-4
TTD Drug ID
D00IBN
Formula
C15H13N3O4S
Canonical SMILES
CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3
InChI
1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
InChIKey
QYSPLQLAKJAUJT-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
Benzothiazine metabolite DM002870
54676301
Oxidation - 5'-Hydroxylation 1 [4] , [5]
Carboxybenzothiazine metabolite DM002873
54687244
Unclear 1 [4] , [5]
Cyclodehydrated metabolite DM002872
12692875
Unclear 1 [4] , [5]
5'-hydroxypiroxicam glucuronide DM002871 N. A. Conjugation - Glucuronidation 2 [4] , [5]
Benzothiazine metabolite DM002870
54676301
Unclear 2 [4] , [5]
N-Methylsaccharin DM002875
27290
Unclear 3 [4] , [5]
Saccharin DM002876
5143
Unclear 4 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002064 Piroxicam 5'-hydroxypiroxicam Oxidation - 5'-Hydroxylation CYP2C9 [4], [5]
MR002065 Piroxicam Cyclodehydrated metabolite Unclear Unclear [4], [5]
MR002066 Piroxicam Carboxybenzothiazine metabolite Unclear Unclear [4], [5]
MR002060 5'-hydroxypiroxicam 5'-hydroxypiroxicam glucuronide Conjugation - Glucuronidation Unclear [4], [5]
MR002061 Carboxybenzothiazine metabolite Benzothiazine metabolite Unclear Unclear [4], [5]
MR002062 Benzothiazine metabolite N-Methylsaccharin Unclear Unclear [4], [5]
MR002063 N-Methylsaccharin Saccharin Unclear Unclear [4], [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
References
1 Piroxicam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Efficacy of piroxicam for postoperative pain after lower third molar surgery associated with CYP2C8*3 and CYP2C9 J Pain Res. 2017 Jul 6;10:1581-1589.
3 Functional characterization of human CYP2C9 allelic variants in COS-7 cells. Front Pharmacol. 2016 Apr 25;7:98.
4 In vivo Piroxicam Metabolites: Possible Source for Synthesis of Central Nervous System (CNS) Acting Depressants Cent Nerv Syst Agents Med Chem. 2017;17(3):172-177. doi: 10.2174/1871524917666161111093759.
5 Metabolism of piroxicam by laboratory animals Drug Metab Dispos. 1981 Mar-Apr;9(2):114-8.

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