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Identification
NameNimesulide
Accession NumberDB04743
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

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 Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AinexNot Available
AulinNot Available
CoxtalNot Available
EskaflamNot Available
Mesulid Not Available
NilsidNot Available
NimaloxNot Available
NimsideNot Available
NiseNot Available
OctaprinNot Available
SintalginNot Available
SulideNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIV4TKW1454M
CAS number51803-78-2
WeightAverage: 308.31
Monoisotopic: 308.046692194
Chemical FormulaC13H12N2O5S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Sulfanilide
  • Nitrobenzene
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Ether
  • Hydrocarbon derivative
  • Organic salt
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.
PharmacodynamicsFood, gender and advanced age have negligible effects on nimesulide pharmacokinetics.
Mechanism of actionThe 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.
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein binding>97.5%
Metabolism

Hepatic. Extensive biotransformation, mainly to 4-hydroxynimesulide (which also appears to be biologically active).

Route of eliminationRenal (50%), fecal (29%)
Half life1.8–4.7 hours
ClearanceNot Available
ToxicityOral TDLO (human): 1.429 mg/kg; Oral TDLO (woman): 2 mg/kg; Oral LD50 (rat): 200 mg/kg; Oral LD50 (mouse): 392 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point143-144.5 °CPhysProp
logP2.60SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0182 mg/mLALOGPS
logP2.56ALOGPS
logP1.79ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.86ChemAxon
pKa (Strongest Basic)-8.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area101.22 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.31 m3·mol-1ChemAxon
Polarizability28.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 ReferencesNot Available
External Links
ATC CodesM02AA26M01AX17
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (23.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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. [PubMed:11752352 ]
  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. [PubMed:16846549 ]
Kind
Protein
Organism
Human
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
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. [PubMed:10592235 ]
Kind
Protein
Organism
Human
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 multifunctional protein found in exocrine fluids such as breast milk and mucosal secretions. Has antimicrobial activity, which depends on the extracellular cation concentration. Antimicrobial properties incl...
Gene Name:
LTF
Uniprot ID:
P02788
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. [PubMed:10592235 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24