Identification
- Summary
Nimesulide is a cyclooxygenase 2 inhibitor used to treat acute pain and primary dysmenorrhea.
- Generic Name
- Nimesulide
- DrugBank Accession Number
- DB04743
- Background
Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Nimesulide (DB04743)
- Weight
- Average: 308.31
Monoisotopic: 308.046692194 - Chemical Formula
- C13H12N2O5S
- Synonyms
- Nimesulida
- Nimesulide
- Nimesulidum
- External IDs
- R 805
- R-805
Pharmacology
- Indication
For the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Menstrual cramps •••••••••••• Used in combination to treat Pain Combination Product in combination with: Lidocaine (DB00281) •••••••••••• ••••• Treatment of Pain •••••••••••• •••••••• ••• ••••••••• •••••••• ••• ••••••••••• ••••••• •••••• Treatment of Pain, acute •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Food, gender and advanced age have negligible effects on nimesulide pharmacokinetics.
- Mechanism of action
The therapeutic effects of Nimesulide are the result of its complete mode of action which targets a number of key mediators of the inflammatory process such as: COX-2 mediated prostaglandins, free radicals, proteolytic enzymes and histamine.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UGroup IIE secretory phospholipase A2 Not Available Humans ULactotransferrin Not Available Humans - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
Not Available
- Protein binding
>97.5%
- Metabolism
Hepatic. Extensive biotransformation, mainly to 4-hydroxynimesulide (which also appears to be biologically active).
- Route of elimination
Renal (50%), fecal (29%)
- Half-life
1.8–4.7 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral TDLO (human): 1.429 mg/kg; Oral TDLO (woman): 2 mg/kg; Oral LD50 (rat): 200 mg/kg; Oral LD50 (mouse): 392 mg/kg
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Nimesulide may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Nimesulide can be increased when it is combined with Abametapir. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Nimesulide is combined with Abciximab. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Nimesulide is combined with Abrocitinib. Acarbose The risk or severity of hypoglycemia can be increased when Nimesulide is combined with Acarbose. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Ainex / Aulin / Eskaflam / Mesulid / Nilsid / Nimalox / Nise / Sulide
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image DOLOFAST PLUS %1+%5 JEL, 30 GRAM Nimesulide (1 %) + Lidocaine (5 %) Gel Topical DİNÇSA İLAÇ SAN. VE TİC. A.Ş. 2019-09-24 Not applicable Turkey 
DOLOFAST PLUS %1+%5 JEL, 50 GRAM Nimesulide (1 %) + Lidocaine (5 %) Gel Topical DİNÇSA İLAÇ SAN. VE TİC. A.Ş. 2019-09-24 Not applicable Turkey EMULİD PLUS % 1 + % 5 JEL Nimesulide (1 %) + Lidocaine (5 %) Gel Topical VEM İLAÇ SAN. VE TİC. A.Ş. 2015-10-20 Not applicable Turkey ETNA COMBO %1 / %0.25 JEL Nimesulide (1 %) + Thiocolchicoside (0.25 %) Gel Topical GENVEON İLAÇ SAN. VE TİC. A.Ş. 2019-07-31 2021-10-04 Turkey ETNA COMBO 100 MG/8 MG TABLET, 14 ADET Nimesulide (100 mg) + Thiocolchicoside (8 mg) Tablet Oral GENVEON İLAÇ SAN. VE TİC. A.Ş. 2019-04-08 Not applicable Turkey
Categories
- ATC Codes
- M01AX17 — Nimesulide
- M01AX — Other antiinflammatory and antirheumatic agents, non-steroids
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amides
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiarrhythmic agents
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antiplatelet agents
- Antirheumatic Agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Peripheral Nervous System Agents
- Selective Cyclooxygenase 2 Inhibitors (NSAIDs)
- Sensory System Agents
- Sulfones
- Sulfur Compounds
- Topical Products for Joint and Muscular Pain
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylethers
- Direct Parent
- Diphenylethers
- Alternative Parents
- Diarylethers / Sulfanilides / Nitrobenzenes / Nitroaromatic compounds / Phenoxy compounds / Phenol ethers / Organic sulfonamides / Organosulfonamides / Aminosulfonyl compounds / Organic oxoazanium compounds show 6 more
- Substituents
- Allyl-type 1,3-dipolar organic compound / Aminosulfonyl compound / Aromatic homomonocyclic compound / C-nitro compound / Diaryl ether / Diphenylether / Ether / Hydrocarbon derivative / Nitroaromatic compound / Nitrobenzene show 20 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- C-nitro compound, aromatic ether, sulfonamide (CHEBI:44445)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- V4TKW1454M
- CAS number
- 51803-78-2
- InChI Key
- HYWYRSMBCFDLJT-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
- IUPAC Name
- N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
- SMILES
- CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O
References
- Synthesis Reference
Bernard Pirotte, Geraldine Piel, Philippe Neven, Isabelle Delneuville, Joszef Geczy, "Water-soluble nimesulide salt and its preparation, aqueous dolution containing it, nimesulide-based combinations and their uses." U.S. Patent US5756546, issued November, 1991.
US5756546- General References
- Not Available
- External Links
- KEGG Drug
- D01049
- PubChem Compound
- 4495
- PubChem Substance
- 46507721
- ChemSpider
- 4339
- BindingDB
- 50056999
- 53694
- ChEBI
- 44445
- ChEMBL
- CHEMBL56367
- ZINC
- ZINC000004617749
- Therapeutic Targets Database
- DPR000079
- PharmGKB
- PA137179528
- PDBe Ligand
- NIM
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Nimesulide
- PDB Entries
- 1zwp / 2oth / 3e9x / 3n8x / 4eix
- MSDS
- Download (23.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Fibromyalgia 1 4 Completed Treatment Osteoarthritis of the Knee 1 4 Completed Treatment Pharyngitis 1 4 Withdrawn Treatment Upper Respiratory Tract Infection 1 3 Completed Treatment Acute and Chronic Inflammation / Dyspepsia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral 100 mg Aerosol, foam Cutaneous 3 % Gel Cutaneous 3 % Mouthwash Oral Tablet, film coated Oral 100 mg Granule, for solution Oral 100 MG Gel Topical 3 % Tablet Oral 50 MG Tablet Oral 100 mg Suspension Oral 1 g Mouthwash Oral 0.1 % Capsule Tablet, coated Oral Spray Topical Gel Topical Gel Topical 1 % Tablet Oral 200 MG Suspension Oral 1000 mg Granule, for suspension Oral Suppository Rectal Tablet Oral Gel 2 %w/w Gel Topical 3 g Gel Topical 2 g Powder, for solution Oral 100 mg Granule, for suspension Oral 400 MG Tablet Oral 400 MG Gel Topical Tablet Oral Capsule, liquid filled Oral 100 mg Granule, for solution Oral Granule Oral 100 MG Suppository Rectal 200 MG Granule, for suspension Oral 50 MG Tablet, effervescent Oral 100 MG Tablet, chewable Oral Capsule 100 MG Suspension Oral Tablet, orally disintegrating Tablet Oral 461.74 mg Granule Oral Powder Oral Suspension Oral 50 mg Granule, for suspension Oral 100 MG Powder, for suspension Oral 100 MG Powder Oral 100 mg/1sachet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 143-144.5 °C PhysProp logP 2.60 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 0.0182 mg/mL ALOGPS logP 2.56 ALOGPS logP 1.79 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 6.7 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 98.54 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 75.3 m3·mol-1 Chemaxon Polarizability 28.93 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9952 Blood Brain Barrier + 0.6341 Caco-2 permeable - 0.55 P-glycoprotein substrate Non-substrate 0.8267 P-glycoprotein inhibitor I Non-inhibitor 0.5634 P-glycoprotein inhibitor II Non-inhibitor 0.8129 Renal organic cation transporter Non-inhibitor 0.8943 CYP450 2C9 substrate Non-substrate 0.6235 CYP450 2D6 substrate Non-substrate 0.8055 CYP450 3A4 substrate Substrate 0.5257 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.7628 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8952 Ames test AMES toxic 0.6488 Carcinogenicity Non-carcinogens 0.6116 Biodegradation Not ready biodegradable 0.9901 Rat acute toxicity 3.0832 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5345 hERG inhibition (predictor II) Non-inhibitor 0.5574
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.710146 predictedDarkChem Lite v0.1.0 [M-H]- 184.698636 predictedDarkChem Lite v0.1.0 [M-H]- 155.17285 predictedDeepCCS 1.0 (2019) [M+H]+ 177.1196211 predictedDarkChem Lite v0.1.0 [M+H]+ 185.670236 predictedDarkChem Lite v0.1.0 [M+H]+ 157.53085 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.1027333 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.700436 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.24092 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phospholipase a2 activity
- Specific Function
- PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
- Gene Name
- PLA2G2E
- Uniprot ID
- Q9NZK7
- Uniprot Name
- Group IIE secretory phospholipase A2
- Molecular Weight
- 15988.525 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine-type endopeptidase activity
- Specific Function
- Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate.Lactotransferrin is a major iron-binding and multifu...
- Gene Name
- LTF
- Uniprot ID
- P02788
- Uniprot Name
- Lactotransferrin
- Molecular Weight
- 78181.225 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]
Drug created at September 11, 2007 17:49 / Updated at June 12, 2021 10:53