Nimesulide

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 Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.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Approved, Investigational, Withdrawn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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMenstrual cramps••••••••••••
Used in combination to treatPainCombination Product in combination with: Lidocaine (DB00281)•••••••••••••••••
Treatment ofPain•••••••••••••••••••• ••• ••••••••• •••••••• ••• ••••••••••• ••••••• ••••••
Treatment ofPain, acute••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
UGroup IIE secretory phospholipase A2Not AvailableHumans
ULactotransferrinNot AvailableHumans
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
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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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbacavirNimesulide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Nimesulide can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Nimesulide is combined with Abciximab.
AbrocitinibThe risk or severity of bleeding and thrombocytopenia can be increased when Nimesulide is combined with Abrocitinib.
AcarboseThe risk or severity of hypoglycemia can be increased when Nimesulide is combined with Acarbose.
Food Interactions
Not Available

Products

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International/Other Brands
Ainex / Aulin / Eskaflam / Mesulid / Nilsid / Nimalox / Nise / Sulide
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DOLOFAST PLUS %1+%5 JEL, 30 GRAMNimesulide (1 %) + Lidocaine (5 %)GelTopicalDİNÇSA İLAÇ SAN. VE TİC. A.Ş.2019-09-24Not applicableTurkey flag
DOLOFAST PLUS %1+%5 JEL, 50 GRAMNimesulide (1 %) + Lidocaine (5 %)GelTopicalDİNÇSA İLAÇ SAN. VE TİC. A.Ş.2019-09-24Not applicableTurkey flag
EMULİD PLUS % 1 + % 5 JELNimesulide (1 %) + Lidocaine (5 %)GelTopicalVEM İLAÇ SAN. VE TİC. A.Ş.2015-10-20Not applicableTurkey flag
ETNA COMBO %1 / %0.25 JELNimesulide (1 %) + Thiocolchicoside (0.25 %)GelTopicalGENVEON İLAÇ SAN. VE TİC. A.Ş.2019-07-312021-10-04Turkey flag
ETNA COMBO 100 MG/8 MG TABLET, 14 ADETNimesulide (100 mg) + Thiocolchicoside (8 mg)TabletOralGENVEON İLAÇ SAN. VE TİC. A.Ş.2019-04-08Not applicableTurkey flag

Categories

ATC Codes
M01AX17 — NimesulideM02AA26 — Nimesulide
Drug Categories
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
KEGG Drug
D01049
PubChem Compound
4495
PubChem Substance
46507721
ChemSpider
4339
BindingDB
50056999
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentFibromyalgia1
4CompletedTreatmentOsteoarthritis of the Knee1
4CompletedTreatmentPharyngitis1
4WithdrawnTreatmentUpper Respiratory Tract Infection1
3CompletedTreatmentAcute and Chronic Inflammation / Dyspepsia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral100 mg
Aerosol, foamCutaneous3 %
GelCutaneous3 %
MouthwashOral
Tablet, film coatedOral100 mg
Granule, for solutionOral100 MG
GelTopical3 %
TabletOral50 MG
TabletOral100 mg
SuspensionOral1 g
MouthwashOral0.1 %
Capsule
Tablet, coatedOral
SprayTopical
GelTopical
GelTopical1 %
TabletOral200 MG
SuspensionOral1000 mg
Granule, for suspensionOral
SuppositoryRectal
TabletOral
Gel2 %w/w
GelTopical3 g
GelTopical2 g
Powder, for solutionOral100 mg
Granule, for suspensionOral400 MG
TabletOral400 MG
GelTopical
TabletOral
Capsule, liquid filledOral100 mg
Granule, for solutionOral
GranuleOral100 MG
SuppositoryRectal200 MG
Granule, for suspensionOral50 MG
Tablet, effervescentOral100 MG
Tablet, chewableOral
Capsule100 MG
SuspensionOral
Tablet, orally disintegrating
TabletOral461.74 mg
GranuleOral
PowderOral
SuspensionOral50 mg
Granule, for suspensionOral100 MG
Powder, for suspensionOral100 MG
PowderOral100 mg/1sachet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)143-144.5 °CPhysProp
logP2.60SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0182 mg/mLALOGPS
logP2.56ALOGPS
logP1.79Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.7Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area98.54 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity75.3 m3·mol-1Chemaxon
Polarizability28.93 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.6341
Caco-2 permeable-0.55
P-glycoprotein substrateNon-substrate0.8267
P-glycoprotein inhibitor INon-inhibitor0.5634
P-glycoprotein inhibitor IINon-inhibitor0.8129
Renal organic cation transporterNon-inhibitor0.8943
CYP450 2C9 substrateNon-substrate0.6235
CYP450 2D6 substrateNon-substrate0.8055
CYP450 3A4 substrateSubstrate0.5257
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.7628
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8952
Ames testAMES toxic0.6488
CarcinogenicityNon-carcinogens0.6116
BiodegradationNot ready biodegradable0.9901
Rat acute toxicity3.0832 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5345
hERG inhibition (predictor II)Non-inhibitor0.5574
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4i-0459000000-055f5763b37c21230aaa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000x-0291000000-646d9ba99afae997e8ed
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000x-0291000000-d80621f80ce111da876f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0910000000-a5c76988cf3380fc5b30
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-d75eef7fee376750fef9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-3e21c4ed858c88f9fc59
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0459000000-055f5763b37c21230aaa
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ue9-2920000000-2d4d6a28e043baa5549a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.710146
predicted
DarkChem Lite v0.1.0
[M-H]-184.698636
predicted
DarkChem Lite v0.1.0
[M-H]-155.17285
predicted
DeepCCS 1.0 (2019)
[M+H]+177.1196211
predicted
DarkChem Lite v0.1.0
[M+H]+185.670236
predicted
DarkChem Lite v0.1.0
[M+H]+157.53085
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.1027333
predicted
DarkChem Lite v0.1.0
[M+Na]+184.700436
predicted
DarkChem Lite v0.1.0
[M+Na]+164.24092
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Rainsford KD: Nimesulide -- a multifactorial approach to inflammation and pain: scientific and clinical consensus. Curr Med Res Opin. 2006 Jun;22(6):1161-70. [Article]
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
  1. 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
  1. 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
  1. 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