Nimesulide

M01A - NSAIDs and antirheumatic products, non-steroids ATC M01AX17 Small molecule Natural product Withdrawn Black-box warning

🧬 Cross-allergy: NSAIDs

JFDA label: Ventor TAB

⚠ Black-Box Warning

Drug Withdrawn from Market — ChEMBL drug_warning (Withdrawn) | Nigeria; Bhutan; Ireland | Adverse health effects
Withdrawn: hepatotoxicity — ChEMBL drug_warning (Withdrawn) | Nigeria; Bhutan; Ireland | Hepatoxicity and neonatal renal failure
Withdrawn: nephrotoxicity — ChEMBL drug_warning (Withdrawn) | Nigeria; Bhutan; Ireland | Hepatoxicity and neonatal renal failure

Indications

Approved

Arthralgia — Arthralgia
Myalgia — Myalgia
Rheumatic Diseases — rheumatic disease

Off-label

Breast Neoplasms

Class profile

cox1_IC50_uM	1000.0
cox2_IC50_uM	2.7
cox2_selectivity	370.3703703703703
inhibitionType	reversible
preferentialCOX2	1
selectiveCOX2	1
plateletEffect	0
source	Warner1999/Vane1996/ChEMBL

Pregnancy & Lactation

Pregnancy

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	C13H12N2O5S
Molecular weight	308.31 g/mol
IUPAC name	N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
CAS	51803-78-2
PubChem CID	4495
InChIKey	`HYWYRSMBCFDLJT-UHFFFAOYSA-N`
logP	2.76 (XLogP 2.6)
Polar surface area	98.54 Å²
H-bond acceptors / donors	5 / 1
Drug-likeness (QED)	0.68
Lipinski violations	0

SMILES

CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1Oc1ccccc1

Biology & Pharmacokinetics

Pharmacokinetics

BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP1A2	Inhibitor	—
CYP2B6	Inhibitor	—
CYP2C19	Substrate	—
CYP2C8	Inhibitor	—
CYP2C9	Inhibitor	—
CYP2C9	Substrate	—
CYP2D6	Substrate	—
CYP3A4	Substrate	—

Receptor binding (top 3)

Target	Action	Affinity
COX-2	Binding	pKi 6.3
COX-2 (PTGS2)	Inhibitor	pIC50 6.2
COX-1	Binding	pKi 6.2

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MDR1 (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)Transporter(unspecified) (Inhibitor)P-gp (Substrate)

Registered Products (3)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Nimes	Tablet 100 mg	15 tab	Reda Jardaneh Drug Store	1.560
Ventor TAB	Tablet 100 mg	30 tab	AL-BARON DRUG STORE	3.280
Nimelide	Tablet 100 mg	30 tab	Orient Montreal Drug Store	3.500