Parecoxib

Active form: Valdecoxib.

JFDA label: Dynastat 40mg

Mechanism of Action

Inhibitor of Prostaglandin G/H synthase 2 — Cyclooxygenase-2 inhibitor

Target	Action	Gene / class
Prostaglandin G/H synthase 2 efficacy	INHIBITOR	PTGS2

Indications

Approved

• Pain, Postoperative — pain
• Rheumatic Diseases — rheumatic disease

Off-label

• Pain
• Renal Colic
• Rib Fractures
• Shoulder Pain

Class profile

cox1_IC50_uM	130.0
cox2_IC50_uM	0.6
cox2_selectivity	216.66666666666669
inhibitionType	reversible
preferentialCOX2	1
selectiveCOX2	1
plateletEffect	0
source	Warner1999/Vane1996/ChEMBL

Adverse Reactions

Cardiac disorders (6)

Not Known Acute coronary syndrome · Bradycardia · Cardiac disorder · Cardiac failure congestive · Myocardial infarction · Tachycardia

Vascular disorders (4)

Not Known Ecchymosis · Hypertension · Hypotension · Orthostatic hypotension

Nervous system disorders (2)

Not Known Cerebrovascular disorder · Dizziness

Hepatobiliary disorders (3)

Not Known Alanine aminotransferase increased · Aspartate aminotransferase increased · Hepatitis

Renal and urinary disorders (4)

Not Known Blood creatinine increased · Renal failure · Renal failure acute · Urinary tract disorder

Blood and lymphatic system disorders (2)

Not Known Anaemia postoperative · Thrombocytopenia

Immune system disorders (3)

Not Known Anaphylactic shock · Hypersensitivity · Immune system disorder

Metabolism and nutrition disorders (2)

Not Known Hyperglycaemia · Hypokalaemia

Gastrointestinal disorders (14)

Not Known Abdominal pain · Constipation · Decreased appetite · Dry mouth · Dyspepsia · Flatulence · Gastrointestinal disorder · Gastrointestinal pain · Gastrointestinal sounds abnormal · Gastrooesophageal reflux disease · Nausea · Oesophagitis · Pancreatitis · Vomiting

Skin and subcutaneous tissue disorders (11)

Not Known Angioedema · Dermatitis · Dermatitis exfoliative · Erythema multiforme · Hyperhidrosis · Pruritus · Rash · Skin disorder · Stevens-Johnson syndrome · Toxic epidermal necrolysis · Urticaria

Musculoskeletal and connective tissue disorders (4)

Not Known Arthralgia · Back pain · Connective tissue disorder · Musculoskeletal discomfort

Psychiatric disorders (2)

Not Known Agitation · Insomnia

Ear and labyrinth disorders (1)

Not Known Ear pain

Infections and infestations (3)

Not Known Infection · Pharyngitis · Wound infection

Investigations (3)

Not Known Blood creatine phosphokinase increased · Blood lactate dehydrogenase increased · Blood urea increased

General disorders and administration site conditions (18)

Not Known Alveolar osteitis · Anaphylactoid reaction · Angiopathy · Asthenia · Hypoaesthesia · Infestation · Injection site pain · Injection site reaction · Malnutrition · Mediastinal disorder · Nervous system disorder · Oedema mouth · Oedema peripheral · Oliguria · Shock · Swelling · Ulcer · Urethral disorder

Respiratory, thoracic and mediastinal disorders (4)

Not Known Bronchospasm · Dyspnoea · Pulmonary embolism · Respiratory failure

Injury, poisoning and procedural complications (1)

Not Known Post procedural complication

Pregnancy & Lactation

Monitoring

Efficacy	Pain and inflammation control (VAS/NRS scores, joint mobility, functional status); minimum effective dose
Toxicity	Blood pressure (raises BP, antagonises antihypertensives); renal function (SCr, eGFR — especially in elderly, heart failure, CKD, dehydrated); Hb/faecal occult blood (GI bleeding); LFTs; oedema
Clinical pearl	Use the lowest effective dose for the shortest duration. Consider co-prescribing a proton pump inhibitor if GI risk factors present. COX-2 selective agents reduce GI but not CV risk.
Counseling	Take with food or milk to reduce GI upset. Report black stools, blood in urine, or significant ankle swelling. Monitor blood pressure regularly if hypertensive.

Chemistry & Properties

Formula	C19H18N2O4S
Molecular weight	370.43 g/mol
IUPAC name	N-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide
CAS	198470-84-7
PubChem CID	119828
InChIKey	TZRHLKRLEZJVIJ-UHFFFAOYSA-N
logP	3.53 (XLogP 3.3)
Polar surface area	89.27 Ų
H-bond acceptors / donors	5 / 1
Drug-likeness (QED)	0.74
Lipinski violations	0

SMILES

CCC(=O)NS(=O)(=O)c1ccc(-c2c(-c3ccccc3)noc2C)cc1

Biology & Pharmacokinetics

Pharmacokinetics predicted

Bioavailability	10.0%
Half-life	0.598 h
Volume of distribution	0.235 L/kg
Protein binding	98.0%
BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP2C19	Substrate	—
CYP2C8	Inhibitor	—
CYP2C9	Substrate	—
CYP3A4	Substrate	—

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OAT1 (Inhibitor)OAT3 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)Transporter(unspecified) (Substrate)

Drug–drug interactions (100+, DDInter)

Interacting drug	Severity	Management
Deferasirox	major
Diatrizoate	major
Everolimus	major
Iohexol	major
Iopamidol	major
Iopromide	major
Iothalamic acid	major
Ioversol	major
Ioxilan	major
Leflunomide	major
Sirolimus	major
Tacrolimus	major
Temsirolimus	major
Teriflunomide	major
Abciximab	moderate
Acetylsalicylic acid	moderate
Alpelisib	moderate
Alteplase	moderate
Amikacin	moderate
Amikacin (liposome)	moderate
Aminolevulinic acid (topical)	moderate
Antithrombin III human	moderate
Apalutamide	moderate
Apixaban	moderate
Aprepitant	moderate
Argatroban	moderate
Asparaginase Escherichia coli	moderate
Balsalazide	moderate
Betamethasone	moderate
Betrixaban	moderate
Bivalirudin	moderate
Brentuximab vedotin	moderate
Brigatinib	moderate
Budesonide	moderate
Cangrelor	moderate
Caplacizumab	moderate
Chlorpropamide	moderate
Cilostazol	moderate
Cimetidine	moderate
Clarithromycin	moderate

Showing 40 of 100+.

Registered Products (2)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Erpasib	Vial Parecoxib 40 mg	5 vial	MS Pharma Jordan	28.910
Dynastat	Ampoule 40 mg	5 amp	Khoury Drug Store	30.720