Piroxicam

Summary

Piroxicam (CHEMBL527) is an approved small-molecule analgesic (ATC M01AC01) targeting PTGS1 and PTGS2; indicated across 11 conditions including eye disorder and rheumatoid arthritis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: M01AC01 (+2 more)
• Targets: 2 (PTGS1, PTGS2)
• Indications: 11 conditions
• Clinical trials: 20
• Chemistry: 331.3 Da · C15H13N3O4S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL527
Name	Piroxicam
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	54676228
ChEBI	CHEBI:8249
ATC	M01AC01, M02AA07, S01BC06
Molecular formula	C15H13N3O4S
Molecular weight	331.3
InChIKey	QYSPLQLAKJAUJT-UHFFFAOYSA-N

SMILES: CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3

IUPAC name: 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1lambda6,2-benzothiazine-3-carboxamide

ChEBI definition: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with the exocyclic nitrogen of 2-aminopyridine. A non-steroidal anti-inflammatory drug of the oxicam class, it is used to relieve pain and works by preventing the production of endogenous prostaglandins involved in the mediation of pain, stiffness, tenderness and swelling.

Pharmacological roles (ChEBI): analgesic, cyclooxygenase 1 inhibitor, non-steroidal anti-inflammatory drug, EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, antirheumatic drug.

Also known as: Brexidol, CP-16,171, CP-16171, Feldene, Feldene 20, Feldene p, Flamatrol, Kentene, Larapam, NSC-666076, Piroflam 10, Piroflam 20

Parent form; salt/anhydrous children: CHEMBL1418195, CHEMBL2106953

Patent coverage: 32,354 distinct patent families (107,554 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 106,408 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
PTGS1	COX-1	Inhibition	5.89	0%	P23219
PTGS2	COX-2	Inhibition	3.66	0%	P35354

Broader ChEMBL bioactivity targets: 20 (assay-derived). Sample: Lysine-specific demethylase 4E, Ubiquitin carboxyl-terminal hydrolase 2, RecQ-like DNA helicase BLM, 4’-phosphopantetheinyl transferase ffp, Solute carrier family 22 member 6, Organic anion transporter 3, Solute carrier family 22 member 6, Cyclooxygenase, Cyclooxygenase, Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 16 potent at pChembl ≥ 5 of 36 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
BLM	8.05	Potency	8.9	nM	CHEMBL_ACT_4742008
BLM	8.05	Potency	8.9	nM	CHEMBL_ACT_4913969
NFKB1	8	Potency	10	nM	CHEMBL_ACT_3672689
NFKB1	8	Potency	10	nM	CHEMBL_ACT_4585970
P35355	7	IC50	100	nM	CHEMBL_ACT_860476
CYP3A4	5.9	Potency	1259	nM	CHEMBL_ACT_4993968
CYP3A4	5.9	Potency	1259	nM	CHEMBL_ACT_5062839
PTGS1	5.89	IC50	1300	nM	CHEMBL_ACT_1252261
PTGS1	5.88	IC50	1313	nM	CHEMBL_ACT_7726131
P08482	5.5	Potency	3162	nM	CHEMBL_ACT_4857851
CYP2C9	5.4	Potency	3981	nM	CHEMBL_ACT_5016948
CYP2C9	5.4	AC50	3981	nM	CHEMBL_ACT_6041626
SLC22A8	5.31	Ki	4880	nM	CHEMBL_ACT_11003119
CYP2C19	5.2	Potency	6310	nM	CHEMBL_ACT_4018470
CYP2C19	5.2	AC50	6310	nM	CHEMBL_ACT_6056552
PTGS1	5.12	AC50	7540	nM	CHEMBL_ACT_25206583

Target pathways

Aggregated over 2 target gene(s): PTGS1, PTGS2.

Top Reactome pathways

9 total, by targets touching each:

Pathway	Targets	Genes
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)	2	PTGS1, PTGS2
COX reactions	1	PTGS1
Synthesis of 15-eicosatetraenoic acid derivatives	1	PTGS2
Interleukin-10 signaling	1	PTGS2
Interleukin-4 and Interleukin-13 signaling	1	PTGS2
Biosynthesis of DHA-derived SPMs	1	PTGS2
Biosynthesis of EPA-derived SPMs	1	PTGS2
Biosynthesis of DPAn-3 SPMs	1	PTGS2
Biosynthesis of electrophilic ω-3 PUFA oxo-derivatives	1	PTGS2

Dominant GO biological processes

GO term	Targets
prostaglandin biosynthetic process	2
response to oxidative stress	2
regulation of blood pressure	2
cyclooxygenase pathway	2
regulation of cell population proliferation	2
long-chain fatty acid biosynthetic process	2
lipid metabolic process	2
fatty acid metabolic process	2
fatty acid biosynthetic process	2
prostaglandin metabolic process	2
prostanoid biosynthetic process	2
cellular oxidant detoxification	2
embryo implantation	1
response to nematode	1
response to selenium ion	1

Indications & clinical

Indications

11 indications (6 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
eye disorder	4	MONDO:0005328	EFO:0005752
rheumatoid arthritis	4	MONDO:0008383	EFO:0000685
rheumatic disorder	4	MONDO:0005554	EFO:0005755
osteoarthritis	4	MONDO:0005178	MONDO:0005178
injury	3	MONDO:0021178	EFO:0000546
osteoarthritis, knee	2	MONDO:0005416	EFO:0004616
epicondylitis	2	MONDO:0001875	EFO:1001896

4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 20.

Phase distribution

Phase	Trials
PHASE4	6
PHASE3	4
PHASE2/PHASE3	3
PHASE2	2
EARLY_PHASE1	2
Not specified	2
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07281807	PHASE4	NOT_YET_RECRUITING	Comparison of the Pain Levels of Single-Dose Premedication With Piroxicam and Prednisolone on Post-Endodontic Pain in Single-Visit Root Canal Treatment of Premolars
NCT00631514	PHASE4	COMPLETED	Interaction Between Antihypertensives and Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)
NCT00649415	PHASE4	COMPLETED	A Double Blind, Double Dummy, Randomized, Comparative Study Of The Efficacy And Safety Of Valdecoxib 40 Mg Twice Daily, As Needed In The First Menstrual Cycle Day And Then Once A Day, And Piroxicam 40 Mg Once A Day In The Treatment Of Patients With Primary Dysmenorrhea
NCT02253446	PHASE4	COMPLETED	A Comparison of Analgesic İmpacts of Piroxicam and Diclofenac Sodium in the Treatment of Primary Dysmenorrhea
NCT02450487	PHASE4	COMPLETED	Influence of Genotype of CYP2C9 on Clinical Efficacy and Pharmacokinetics of Piroxicam After Lower Third Molar Surgery
NCT05488925	PHASE4	COMPLETED	Comparison of Preoperative Analgesics on the Efficacy of Inferior Alveolar Nerve Block.
NCT06404177	PHASE3	RECRUITING	Enantyum® IV Versus Piroxen® IM in Emergency Pain Management
NCT06727734	PHASE3	RECRUITING	Levonorgestrel-piroxicam Versus Ulipristal Acetate for Emergency Contraception
NCT02304783	PHASE3	COMPLETED	Oral NSAI Versus Paracetamol or Placebo as a Second Line Treatment for Renal Colics
NCT03614494	PHASE2/PHASE3	COMPLETED	Piroxicam and Levonorgestrel Co-treatment for Emergency Contraception
NCT04124822	PHASE2/PHASE3	COMPLETED	Effectiveness if Premedication With Single Dose Piroxicam and Prednisolone After a Single Visit Root Canal Treatment .
NCT04201249	PHASE2/PHASE3	UNKNOWN	Mesotherapy In Lateral Epicondylitis
NCT07475663	PHASE3	COMPLETED	Counterpain PXM Versus Diclofenac Versus Piroxicam
NCT05722782	PHASE2	RECRUITING	Oral NSAI Versus Acetaminophen or Placebo as a Discharge Treatment of Non Complicated Renal Colics
NCT00670475	PHASE2	COMPLETED	Comparative Study of Olive Oil With Piroxicam Gel in Osteoarthritis of the Knee
NCT05104931	PHASE1	COMPLETED	PK Evaluation of a Nanoformed Oral IR Piroxicam Tablet in Healthy Subjects
NCT03612323	EARLY_PHASE1	UNKNOWN	Comparison Between Intraligamentary Piroxicam and Articaine
NCT04062591	EARLY_PHASE1	COMPLETED	Efficacy of Piroxicam as a Perioperative Analgesic for Patients Undergoing Fixation of Maxillofacial Fractures
NCT03998826	Not specified	UNKNOWN	Piroxicam Premedication for Postendodontic Pain in Non-vital Mandibular Molars
NCT06943092	Not specified	COMPLETED	Piroxicam Versus Diclofenac for Post Caesarean Section Analgesia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

407 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
3,3’,4’,5-TETRACHLOROSALICYLANILIDE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ACEMETACIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ASPIRIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
BROMFENAC	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CAPSAICIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CAPTOPRIL	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CARPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CELECOXIB	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CIANIDANOL	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
DEXIBUPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
DEXKETOPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
DICLOFENAC	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
DOXORUBICIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ESFLURBIPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ETODOLAC	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ETORICOXIB	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
FLURBIPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
GLAFENINE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
HEXACHLOROPHENE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
IBUPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
INDOMETHACIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
KETOPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
KETOROLAC	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
LEVODOPA	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
LOXOPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
LUMIRACOXIB	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
MECLOFENAMIC ACID	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
MEFENAMIC ACID	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
MELOXICAM	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
MOFEZOLAC	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
MONOBENZONE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
NAPROXEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
NIMESULIDE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
OMADACYCLINE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
OXAPROZIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
PRIMAQUINE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
RANITIDINE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
ROFECOXIB	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
SELINEXOR	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
SUPROFEN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
TEGASEROD	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
TELOTRISTAT	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
TOLMETIN	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
TROGLITAZONE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
VALDECOXIB	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
VORTIOXETINE	ChEMBL	Phase 4 (approved)	PTGS1, PTGS2
CURCUMIN	ChEMBL	Phase 3	PTGS1, PTGS2
RESVERATROL	ChEMBL	Phase 3	PTGS1, PTGS2
CIMICOXIB	ChEMBL	Phase 2	PTGS1, PTGS2
DERACOXIB	ChEMBL	Phase 2	PTGS1, PTGS2
ENOFELAST	ChEMBL	Phase 2	PTGS1, PTGS2
FIROCOXIB	ChEMBL	Phase 2	PTGS1, PTGS2
FLUFENAMIC ACID	ChEMBL	Phase 2	PTGS1, PTGS2
LICOFELONE	ChEMBL	Phase 2	PTGS1, PTGS2
MAVACOXIB	ChEMBL	Phase 2	PTGS1, PTGS2
MIROPROFEN	ChEMBL	Phase 2	PTGS1, PTGS2
NIFLUMIC ACID	ChEMBL	Phase 2	PTGS1, PTGS2
PHENOTHIAZINE	ChEMBL	Phase 2	PTGS1, PTGS2
PIRMAGREL	ChEMBL	Phase 2	PTGS1, PTGS2