Nimesulide
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Also known as AulinNimesulidaNSC-758412R 805R-805NimesulidSID11111520SID11111521SID26746940SID26751468SID29215000SID50103974SID855635SID90341133SID56422364SID85231150NimusilideSID124880853SID174007215
Summary
Nimesulide (CHEMBL56367) is an approved small-molecule non-steroidal anti-inflammatory drug (ATC M01AX17) targeting PTGS1, PTGS2, and SLC6A19; indicated across 5 conditions including rheumatic disorder and breast neoplasm.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: M01AX17 (+1 more)
- Targets: 3 (PTGS1, PTGS2, SLC6A19)
- Indications: 5 conditions
- Clinical trials: 5
- Chemistry: 308.31 Da · C13H12N2O5S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL56367 |
| Name | Nimesulide |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 4495 |
| ChEBI | CHEBI:44445 |
| ATC | M01AX17, M02AA26 |
| Molecular formula | C13H12N2O5S |
| Molecular weight | 308.31 |
| InChIKey | HYWYRSMBCFDLJT-UHFFFAOYSA-N |
SMILES: CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2
IUPAC name: N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
ChEBI definition: An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.
Pharmacological roles (ChEBI): non-steroidal anti-inflammatory drug, cyclooxygenase 2 inhibitor.
Also known as: Aulin, Nimesulida, Nimesulide, NSC-758412, R 805, R-805, nimesulide, Nimesulid, SID11111520, SID11111521, SID26746940, SID26751468
Patent coverage: 7,418 distinct patent families (25,455 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 25,343 (100%) 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 | 4.76 | 0% | P23219 |
| PTGS2 | COX-2 | Inhibition | 6.22 | 0% | P35354 |
| SLC6A19 | B0AT1 | Inhibition | 4.64 | 0.3% | Q695T7 |
Broader ChEMBL bioactivity targets: 42 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Survival motor neuron protein, Fructose-bisphosphate aldolase, Prelamin-A/C, RecQ-like DNA helicase BLM, 4’-phosphopantetheinyl transferase ffp, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Vasopressin V2 receptor, Neuronal acetylcholine receptor subunit alpha-4.
Bioactivity
ChEMBL activities: 40 potent at pChembl ≥ 5 of 82 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PTGS2 | 7.82 | IC50 | 15 | nM | CHEMBL_ACT_180239 |
| PTGS2 | 7.64 | IC50 | 23 | nM | CHEMBL_ACT_6190264 |
| PTGS1 | 7.29 | AC50 | 50.7 | nM | CHEMBL_ACT_25206774 |
| TSHR | 7 | Potency | 100 | nM | CHEMBL_ACT_3910915 |
| LMNA | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_3639514 |
| P79208 | 6.4 | IC50 | 400 | nM | CHEMBL_ACT_5247647 |
| PTGS2 | 6.22 | IC50 | 600 | nM | CHEMBL_ACT_1437276 |
| PTGS2 | 6.16 | IC50 | 700 | nM | CHEMBL_ACT_12165665 |
| PTGS2 | 6.16 | IC50 | 700 | nM | CHEMBL_ACT_13905558 |
| PTGS2 | 6.16 | IC50 | 700 | nM | CHEMBL_ACT_1842583 |
| PTGS2 | 6.16 | IC50 | 700 | nM | CHEMBL_ACT_3218345 |
| PTGS1 | 5.91 | IC50 | 1226 | nM | CHEMBL_ACT_7718538 |
| PTGS2 | 5.89 | IC50 | 1300 | nM | CHEMBL_ACT_1251845 |
| PTGS2 | 5.85 | AC50 | 1400 | nM | CHEMBL_ACT_25166861 |
| PTGS2 | 5.84 | IC50 | 1436 | nM | CHEMBL_ACT_7718540 |
| PTGS2 | 5.78 | IC50 | 1680 | nM | CHEMBL_ACT_25035075 |
| PTGS2 | 5.77 | IC50 | 1684 | nM | CHEMBL_ACT_22908261 |
| P79208 | 5.72 | IC50 | 1920 | nM | CHEMBL_ACT_15759717 |
| MPO | 5.68 | IC50 | 2100 | nM | CHEMBL_ACT_12112449 |
| HIF1A | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4126750 |
| HIF1A | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4520161 |
| CYP2C9 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_5077376 |
| CYP2C9 | 5.5 | AC50 | 3162 | nM | CHEMBL_ACT_5997284 |
| PTGS2 | 5.46 | IC50 | 3500 | nM | CHEMBL_ACT_2500701 |
| PTGS1 | 5.42 | IC50 | 3760 | nM | CHEMBL_ACT_12165666 |
| PTGS1 | 5.42 | IC50 | 3760 | nM | CHEMBL_ACT_13905579 |
| PTGS1 | 5.42 | IC50 | 3760 | nM | CHEMBL_ACT_1842554 |
| PTGS1 | 5.42 | IC50 | 3760 | nM | CHEMBL_ACT_3218306 |
| GLA | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_4836906 |
| CCKAR | 5.21 | AC50 | 6200 | nM | CHEMBL_ACT_25178876 |
Target pathways
Aggregated over 3 target gene(s): PTGS1, PTGS2, SLC6A19.
Top Reactome pathways
20 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Synthesis of Prostaglandins (PG) and Thromboxanes (TX) | 2 | PTGS1, PTGS2 |
| COX reactions | 1 | PTGS1 |
| Disease | 1 | SLC6A19 |
| Synthesis of 15-eicosatetraenoic acid derivatives | 1 | PTGS2 |
| Amino acid transport across the plasma membrane | 1 | SLC6A19 |
| Transport of small molecules | 1 | SLC6A19 |
| R-HSA-425366 | 1 | SLC6A19 |
| R-HSA-425393 | 1 | SLC6A19 |
| SLC-mediated transmembrane transport | 1 | SLC6A19 |
| SLC-mediated transport of neurotransmitters | 1 | SLC6A19 |
| Defective transport of neurotransmitters by SLC6A19 causes Hartnup disorder (HND) | 1 | SLC6A19 |
| SLC transporter disorders | 1 | SLC6A19 |
| Disorders of transmembrane transporters | 1 | SLC6A19 |
| Defective transport of amino acids by SLC6A19 causes Hartnup disorder (HND) | 1 | SLC6A19 |
| 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
5 indications (3 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 |
| breast neoplasm | 2 | MONDO:0021100 | MONDO:0007254 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 5.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 2 |
| PHASE2 | 2 |
| PHASE3 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01257126 | PHASE4 | WITHDRAWN | Efficacy of Diclofenac Potassium vs Nimesulide in the Treatment of Fever and Pain in Children With Upper Respiratory Tract Infection |
| NCT02229747 | PHASE4 | COMPLETED | Efficacy and Safety of Meloxicam Suspension Versus Diclofenac Suspension or Nimesulide Suspension in Patients With a Diagnosis of Acute, Non-bacterial Pharyngitis, Pharyngotonsillitis or Laryngitis |
| NCT01670552 | PHASE3 | COMPLETED | Evaluation of Two Therapies for the Treatment of Osteoarticular Inflammation in Dyspeptic Patients |
| NCT01500577 | PHASE2 | COMPLETED | A Prevention Trial in Subjects at High Risk for Breast Cancer |
| NCT04609748 | PHASE2 | UNKNOWN | Comparative Analysis of the Effectiveness of the Use of Nimesulide and CBD Oil in Patients With Pain in the Preauricular Region Due to the Pain-dysfunctional Syndrome of the Temporomandibular Joint. |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
408 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 |
| OMADACYCLINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| OXAPROZIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| PIROXICAM | 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 |
Related Atlas pages
- Genes: PTGS1, PTGS2, SLC6A19
- Diseases: rheumatic disorder
- Drugs: 3,3’,4’,5-TETRACHLOROSALICYLANILIDE, Acemetacin, Aspirin, Bromfenac, Capsaicin, Captopril, Carprofen, Celecoxib, Cianidanol, Dexibuprofen, Dexketoprofen, Diclofenac, Diethylstilbestrol, Doxorubicin, Esflurbiprofen, Etodolac, Etoricoxib, Flurbiprofen, Glafenine, Hexachlorophene, Ibuprofen, Indomethacin, Ketorolac, Levodopa, Loxoprofen, Lumiracoxib, Meclofenamic Acid, Mefenamic Acid, Meloxicam, Mofezolac, Monobenzone, Naproxen, Omadacycline, Oxaprozin, Piroxicam, Primaquine, Ranitidine, Rofecoxib, Selinexor, Suprofen, Tegaserod, Telotristat, Tolmetin, Troglitazone, Valdecoxib, Vortioxetine, Curcumin, Resveratrol