Valdecoxib

Summary

Valdecoxib (CHEMBL865) is an approved small-molecule non-steroidal anti-inflammatory drug (ATC M01AH03) targeting PTGS2 and CA12; indicated across 8 conditions including rheumatic disorder and osteoarthritis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: M01AH03
• Targets: 2 (PTGS2, CA12)
• Indications: 8 conditions
• Clinical trials: 26
• Chemistry: 314.4 Da · C16H14N2O3S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL865
Name	Valdecoxib
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	119607
ChEBI	CHEBI:63634
ATC	M01AH03
Molecular formula	C16H14N2O3S
Molecular weight	314.4
InChIKey	LNPDTQAFDNKSHK-UHFFFAOYSA-N

SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C3=CC=C(C=C3)S(=O)(=O)N

IUPAC name: 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide

ChEBI definition: A member of the class of isoxazoles that is isoxazole which is substituted at positions 3, 4 and 5 by phenyl, p-sulfamoylphenyl and methyl groups, respectively. A selective cyclooxygenase 2-inhibitor, it used as a nonsteroidal anti-inflammatory drug (NSAID) for the treatment of arthritis from 2001 until 2005, when it was withdrawn following concerns of an associated increased risk of heart attack and stroke.

Pharmacological roles (ChEBI): non-steroidal anti-inflammatory drug, cyclooxygenase 2 inhibitor, non-narcotic analgesic, antirheumatic drug, antipyretic.

Also known as: Bextra, NSC-759846, SC-65872, Valdecoxib, Valdyn, Valdyn (previously kudeq), valdecoxib, SID26748964, VALDECOXIB, SID49665731, SID144204991, SID170465163

Patent coverage: 10,077 distinct patent families (41,681 SureChEMBL compound mentions), from 1 matched compound structure(s). 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
PTGS2	COX-2	Inhibition	8.3	0%	P35354
CA12	carbonic anhydrase 12	Inhibition	7.89	0.2%	O43570

Broader ChEMBL bioactivity targets: 34 (assay-derived). Sample: Prelamin-A/C, Alpha-2B adrenergic receptor, Carbonic anhydrase 2, Beta-2 adrenergic receptor, Beta-1 adrenergic receptor, Muscarinic acetylcholine receptor M1, Carbonic anhydrase 13, Prostaglandin G/H synthase 1, Sodium-dependent noradrenaline transporter, Adenosine receptor A1.

Bioactivity

ChEMBL activities: 102 potent at pChembl ≥ 5 of 154 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS2	8.3	IC50	5.01	nM	CHEMBL_ACT_143350
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_1600140
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_18748607
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_18940840
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_396582
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_404750
PTGS2	8.3	IC50	5	nM	CHEMBL_ACT_413146
CA12	7.89	Ki	13	nM	CHEMBL_ACT_12142064
CA12	7.89	Ki	13	nM	CHEMBL_ACT_13440636
CA12	7.89	Ki	13	nM	CHEMBL_ACT_13910687
CA12	7.89	Ki	13	nM	CHEMBL_ACT_1666721
CA12	7.89	Ki	13	nM	CHEMBL_ACT_6389208
PTGS1	7.77	AC50	17.1	nM	CHEMBL_ACT_25206676
CA9	7.57	Ki	27	nM	CHEMBL_ACT_12142065
CA9	7.57	Ki	27	nM	CHEMBL_ACT_13440657
CA9	7.57	Ki	27	nM	CHEMBL_ACT_13910708
CA9	7.57	Ki	27	nM	CHEMBL_ACT_1666715
CA9	7.57	Ki	27	nM	CHEMBL_ACT_2496785
CA9	7.57	Ki	27	nM	CHEMBL_ACT_40288
CA9	7.57	Ki	27	nM	CHEMBL_ACT_6389191
CA9	7.57	IC50	27	nM	CHEMBL_ACT_666274
PTGS2	7.4	IC50	40	nM	CHEMBL_ACT_2064497
CA2	7.37	Ki	43	nM	CHEMBL_ACT_10946407
CA2	7.37	Ki	43	nM	CHEMBL_ACT_12142072
CA2	7.37	Ki	43	nM	CHEMBL_ACT_12161326
CA2	7.37	Ki	43	nM	CHEMBL_ACT_12655975
CA2	7.37	Ki	43	nM	CHEMBL_ACT_13286811
CA2	7.37	Ki	43	nM	CHEMBL_ACT_13407612
CA2	7.37	Ki	43	nM	CHEMBL_ACT_13440699
CA2	7.37	Ki	43	nM	CHEMBL_ACT_13866455

Target pathways

Aggregated over 2 target gene(s): PTGS2, CA12.

Top Reactome pathways

10 total, by targets touching each:

Pathway	Targets	Genes
Metabolism	1	CA12
Reversible hydration of carbon dioxide	1	CA12
Synthesis of 15-eicosatetraenoic acid derivatives	1	PTGS2
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)	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	1
response to oxidative stress	1
embryo implantation	1
regulation of blood pressure	1
response to nematode	1
response to selenium ion	1
positive regulation of vascular endothelial growth factor production	1
cyclooxygenase pathway	1
lipoxygenase pathway	1
positive regulation of prostaglandin biosynthetic process	1
positive regulation of fever generation	1
prostaglandin secretion	1
regulation of cell population proliferation	1
long-chain fatty acid biosynthetic process	1
positive regulation of nitric oxide biosynthetic process	1

Indications & clinical

Indications

8 indications (4 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
rheumatic disorder	4	MONDO:0005554	EFO:0005755
osteoarthritis	4	MONDO:0005178	MONDO:0005178
rheumatoid arthritis	4	MONDO:0008383	EFO:0000685
pharyngitis	3	MONDO:0002258	MONDO:0002258
pancreatitis	2	MONDO:0004982	EFO:0000278
osteoarthritis, knee	2	MONDO:0005416	EFO:0004616

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

Clinical trials

Total trials: 26.

Phase distribution

Phase	Trials
PHASE4	10
PHASE3	10
Not specified	3
PHASE2	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00122096	PHASE4	COMPLETED	Perioperative Inflammation and Cyclooxygenase 2 (COX-2)
NCT00260325	PHASE4	COMPLETED	Effect of Valdecoxib Pretreatment on Pain and Secondary Hyperalgesia in Healthy Volunteers
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
NCT00649610	PHASE4	COMPLETED	Randomized, Double Blind, Multicenter Study of the Safety and Efficacy of Valdecoxib 40 mg Once Daily Compared With Diclofenac 75 mg Twice Daily in Acute Low Back Pain
NCT00650455	PHASE4	COMPLETED	Efficacy and Safety of Valdecoxib and Naproxen in Treating the Signs and Symptoms of Rheumatoid Arthritis (RA) in a Severe Rheumatoid Arthritis Patients
NCT00650598	PHASE4	COMPLETED	A Multicentre, Double-Blind, Double-Dummy, Randomised Study of the Analgesic Efficacy and Safety of Valdecoxib Compared to Diclofenac Sodium in Patients Undergoing Knee Arthroscopy for Anterior Cruciate Ligament (ACL) Reconstruction
NCT00657449	PHASE4	TERMINATED	A Double-blind, Double-dummy, Multicenter, Randomized Study of the Efficacy and Tolerability of Valdecoxib 40 mg Versus Rofecoxib 50 mg in Treating the Symptoms of Ankle Sprain
NCT00660855	PHASE4	TERMINATED	A Multicenter, Open Label Trial To Evaluate Pain Relief With Intravenous Followed By Oral Therapy With Parecoxib/Valdecoxib 40 Mg/Day For Treatment Of Post-Laparoscopic Surgery Pain
NCT00671320	PHASE4	COMPLETED	A Multi-Center, Randomized, Double-Blind, Parallel Group Study To Compare The Efficacy And Tolerability Of Valdecoxib And Diclofenac In Patients With A Sprained Ankle
NCT01361789	PHASE4	COMPLETED	COX-2 Inhibitor Versus Glucocorticoid Versus Both Combined
NCT00092300	PHASE3	COMPLETED	A Study of Two Approved Drugs in the Treatment of Postoperative Dental Pain (0966-181)(COMPLETED)
NCT00419549	PHASE2/PHASE3	TERMINATED	Efficacy Study of Glyceryl-Trinitrate Patch and Parecoxib (Valdecoxib) for the Prevention of Pancreatitis After Endoscopic Retrograde Cholangiopancreatography (ERCP)
NCT00636064	PHASE3	COMPLETED	A Study Comparing the Efficacy and Safety of Valdecoxib Plus Parecoxib Versus Valdecoxib Plus Placebo for the Treatment of Pain After Coronary Artery Bypass Surgery
NCT00647829	PHASE3	COMPLETED	A Comparison Of Valdecoxib 20 Mg Twice Daily and 40 Mg Daily and Placebo In The Treatment Of Sore Throat
NCT00648258	PHASE3	COMPLETED	A Double-Blind, Double Dummy, Randomized Comparison Study Of The Efficacy And Safety Of Valdecoxib 10mg Once Daily And Naproxen 500mg Twice Daily In Treating The Signs And Symptoms Of Osteoarthritis Of The Knee Or Hip In Taiwan
NCT00650039	PHASE3	COMPLETED	Double-Blind, Randomized Study Of The Analgesic Efficacy And Safety Of Valdecoxib 20 Mg Daily And Valdecoxib 20 Mg Twice Daily Compared To Placebo For Management Of Acute Postsurgical Pain In Anterior Cruciate Ligament (ACL) Reconstruction
NCT00651300	PHASE3	TERMINATED	A Study of the Recovery Benefits After Treatment With Parecoxib/Valdecoxib in Patients Undergoing Abdominal Surgery
NCT00652808	PHASE3	COMPLETED	Double-Blind, Double Dummy, Randomized Comparison Study to Evaluate the Efficacy and Safety of Valdecoxib 10 mg Once Daily and Naproxen 500 mg Twice Daily in Treating the Signs and Symptoms of Osteoarthritis of the Knee
NCT00653354	PHASE3	COMPLETED	Analgesic Efficacy Of Valdecoxib In Patients Following Bunion Surgery
NCT00661635	PHASE3	COMPLETED	A Randomized, Double-Blind Study of the Efficacy and Safety of Valdecoxib Compared to Placebo for Treatment of Post- Cholecystectomy Surgery Pain
NCT00683137	PHASE3	COMPLETED	Analgesic Efficacy And Safety of Valdecoxib For Treatment Of Post-Surgical Pain From Bunionectomy Surgery
NCT00115752	PHASE2	COMPLETED	Genetic Basis For Variation In NSAID Analgesia In A Clinical Model Of Acute Pain
NCT00650624	PHASE2	COMPLETED	A Dose-Ranging Study Of Valdecoxib 5 Mg, 10 Mg, And 20 Mg Once Daily Versus Placebo In Patients With Osteoarthritis Of The Knee (Japan)
NCT00021996	Not specified	COMPLETED	Valdecoxib in Treating Chronic Pain in Cancer Patients
NCT00763997	Not specified	COMPLETED	Study of the Effect of Dipyrone, Ibuprofen, Paracetamol and Parecoxib on the Platelet Aggregation in Analgetic Dosages
NCT01541137	Not specified	COMPLETED	NSAIDs With Morphine-PCA Compared to Epidural Analgesia in Thoracotomy Pain

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

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.

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

Molecule	Source	Status	Shared targets
CELECOXIB	ChEMBL	Phase 4 (approved)	CA12, PTGS2
DOBUTAMINE	ChEMBL	Phase 4 (approved)	CA12, PTGS2
INDAPAMIDE	ChEMBL	Phase 4 (approved)	CA12, PTGS2
CURCUMIN	ChEMBL	Phase 3	CA12, PTGS2
QUERCETIN	ChEMBL	Phase 3	CA12, PTGS2
RESVERATROL	ChEMBL	Phase 3	CA12, PTGS2
FIDAXOMICIN	ChEMBL + PubChem	Phase 4 (approved)	PTGS2
PAZOPANIB	ChEMBL + PubChem	Phase 4 (approved)	CA12
3,3’,4’,5-TETRACHLOROSALICYLANILIDE	ChEMBL	Phase 4 (approved)	PTGS2
ABEMACICLIB	ChEMBL	Phase 4 (approved)	PTGS2
ACALABRUTINIB	ChEMBL	Phase 4 (approved)	PTGS2
ACEMETACIN	ChEMBL	Phase 4 (approved)	PTGS2
ACETAMINOPHEN	ChEMBL	Phase 4 (approved)	CA12
ACETAZOLAMIDE	ChEMBL	Phase 4 (approved)	CA12
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	PTGS2
ACETYLCYSTEINE	ChEMBL	Phase 4 (approved)	PTGS2
ACRIVASTINE	ChEMBL	Phase 4 (approved)	PTGS2
AMODIAQUINE	ChEMBL	Phase 4 (approved)	PTGS2
AMPHOTERICIN B	ChEMBL	Phase 4 (approved)	PTGS2
AMSACRINE	ChEMBL	Phase 4 (approved)	PTGS2
ANISINDIONE	ChEMBL	Phase 4 (approved)	PTGS2
APOMORPHINE	ChEMBL	Phase 4 (approved)	PTGS2
ARFORMOTEROL	ChEMBL	Phase 4 (approved)	PTGS2
ASPIRIN	ChEMBL	Phase 4 (approved)	PTGS2
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	PTGS2
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	PTGS2
BEPRIDIL	ChEMBL	Phase 4 (approved)	PTGS2
BIPERIDEN	ChEMBL	Phase 4 (approved)	PTGS2
BORTEZOMIB	ChEMBL	Phase 4 (approved)	CA12
BRINZOLAMIDE	ChEMBL	Phase 4 (approved)	CA12
BROMFENAC	ChEMBL	Phase 4 (approved)	PTGS2
CALCIPOTRIENE	ChEMBL	Phase 4 (approved)	PTGS2
CALCITRIOL	ChEMBL	Phase 4 (approved)	PTGS2
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	PTGS2
CANNABIDIOL	ChEMBL	Phase 4 (approved)	PTGS2
CAPSAICIN	ChEMBL	Phase 4 (approved)	PTGS2
CAPTOPRIL	ChEMBL	Phase 4 (approved)	PTGS2
CARPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
CEFAZOLIN	ChEMBL	Phase 4 (approved)	PTGS2
CEFTIZOXIME	ChEMBL	Phase 4 (approved)	PTGS2
CEPHRADINE	ChEMBL	Phase 4 (approved)	PTGS2
CHLORTHALIDONE	ChEMBL	Phase 4 (approved)	CA12
CIANIDANOL	ChEMBL	Phase 4 (approved)	PTGS2
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	PTGS2
COUMARIN	ChEMBL	Phase 4 (approved)	CA12
CRIZOTINIB	ChEMBL	Phase 4 (approved)	PTGS2
DAUNORUBICIN	ChEMBL	Phase 4 (approved)	PTGS2
DESERPIDINE	ChEMBL	Phase 4 (approved)	PTGS2
DEXIBUPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
DEXKETOPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
DICHLORPHENAMIDE	ChEMBL	Phase 4 (approved)	CA12
DICLOFENAC	ChEMBL	Phase 4 (approved)	PTGS2
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	PTGS2
DORZOLAMIDE	ChEMBL	Phase 4 (approved)	CA12
DOXORUBICIN	ChEMBL	Phase 4 (approved)	PTGS2
EPINEPHRINE	ChEMBL	Phase 4 (approved)	PTGS2
ERGOTAMINE	ChEMBL	Phase 4 (approved)	PTGS2
ESFLURBIPROFEN	ChEMBL	Phase 4 (approved)	PTGS2
ETHOXZOLAMIDE	ChEMBL	Phase 4 (approved)	CA12
ETODOLAC	ChEMBL	Phase 4 (approved)	PTGS2