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N1016 Sigma

Nimesulide

Synonym: N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide

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Description

Biochem/physiol Actions

Highly selective cyclooxygenase-2 inhibitor.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

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DISCOVER Bioactive Small Molecules

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solid

Nimesulide
N0845000Nimesulide

European Pharmacopoeia (EP) Reference Standard

Nimesulide
PHR1336Nimesulide

pharmaceutical secondary standard; traceable to PhEur

Nimesulide for peak identification

European Pharmacopoeia (EP) Reference Standard

NS-398
N194NS-398

≥98% (HPLC), solid

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
Safety Statements (Europe) 
36
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
PB0970000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Biofiles, Central Nervous System, Diseases, Events, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions, Type

Peer-Reviewed Papers

References

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Forthcoming non-steroidal anti-inflammatory drugs: are they really devoid of side effects. Bjarnason Ital. J. Gastroenterol Hepatol. 31, S27-S36, (1999)

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Clinical experience with cyclooxygenase-2 inhibitors. Van Ryn, et al. Inflamm. Res. 48, 247-254, (1999)

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Mechanisms of NSAID-induced hepatotoxicity: focus on nimesulide. Boelsterli UA Drug Saf. 25(9), 633-48, (2002)

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Cyclooxygenase-2 inhibition and thromboxane A(2) receptor antagonism attenuate hypoxic pulmonary vasoconstriction in a porcine model. Kylhammar D and Rådegran G Acta Physiol. (Oxf.) 205(4), 507-19, (2012)

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[Inhibitory effect of nimesulide and oxaliplatin on tumor growth and lymphatic metastasis of transplanted human lung cancer in nude mice]. Lang Z, Chen G, and Wang DC Zhonghua Zhong Liu Za Zhi 34(10), 739-44, (2012)

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Nimesulide-induced acute renal failure. Zaki SA, Nilofer AR, and Taqi SA Saudi J. Kidney Dis. Transpl. 23(6), 1294-6, (2012)

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[Downregulation of HSP70 gene expression and apoptosis in human hepatocellular carcinoma SMMC-7721 cells induced by nimesulide in vitro]. Yin GZ, Tu KS, Han SS, et al. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi 28(9), 933-6, (2012)

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Ocimum Sanctum seeds, a natural superdisintegrant: formulation and evaluation of fast melt tablets of nimesulide. Malik K, Arora G, and Singh I Polim. Med. 42(1), 49-59, (2012)

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Current status of the therapeutic uses and actions of the preferential cyclo-oxygenase-2 NSAID, nimesulide. Rainsford KD Inflammopharmacology 14(3-4), 120-37, (2006)

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The use of nimesulide and its analogues in cancer chemoprevention. Renard JF, Julémont F, de Leval X, et al. Anticancer Agents Med. Chem. 6(3), 233-7, (2006)

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[Nimesulide: a lower risk treatment in rheumatic diseases]. Trnavský K Vnitr. Lek. 50(2), 157-62, (2004)

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Safety of oral use of nimesulide in children: systematic review of randomized controlled trials. Gupta P and Sachdev HP Indian Pediatr. 40(6), 518-31, (2003)

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[Nimesulide (Aulin)--the selective COX-2 inhibitor in the treatment of ENT diseases]. Arcimowicz M, Samoliński B, Gotlib T, et al. Otolaryngol. Pol. 56(4), 501-7, (2002)

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Nimesulide: an NSAID that preferentially inhibits COX-2, and has various unique pharmacological activities. Bennett A and Villa G Expert Opin. Pharmacother. 1(2), 277-86, (2000)

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[Nimesulide - a non-steroidal anti-inflammatory drug, a preferential cyclooxygenase-2 inhibitor]. Bennett A and Vila D Vutr. Boles. 32(1), 33-6, (2000)

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[Toxic hepatitis caused by nimesulide, presentation of a new case and review of the literature]. Ferreiro C, Vivas S, Jorquera F, et al. Gastroenterol. Hepatol. 23(9), 428-30, (2000)

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[The yin yang of inflammation: inducible and constitutive cyclooxygenase. Nimesulide and selective inhibitors of inducible cyclooxygenase]. Cirino G, Coppini A, Bigini C, et al. Eur. Rev. Med. Pharmacol. Sci. 2(3 Suppl 1), 1-8, (1998)

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Amide derivatives of benzene-sulfonanilide, pharmaceutical composition thereof and method for cancer treatment using the same (US20120095092). Supuran CT Expert Opin. Ther. Pat. 22(10), 1251-5, (2012)

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Implication of hepatic transporters (MDR1 and MRP2) in inflammation-associated idiosyncratic drug-induced hepatotoxicity investigated by microvolume cytometry. Saab L, Peluso J, Muller CD, et al. Cytometry. A 83(4), 403-8, (2013)

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Thermosensitive and mucoadhesive in situ gel based on poloxamer as new carrier for rectal administration of nimesulide. Yuan Y, Cui Y, Zhang L, et al. Int. J. Pharm. 430(1-2), 114-9, (2012)

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A review of analytical techniques for determination of oxicams, nimesulide and nabumetone. Starek M and Krzek J Talanta 77(3), 925-42, (2009)

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Nimesulide and hepatic adverse effects: roles of reactive metabolites and host factors. Boelsterli UA Int. J. Clin. Pract. Suppl. (128), 30-6, (2002)

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Natural terpenes prevent mitochondrial dysfunction, oxidative stress and release of apoptotic proteins during nimesulide-hepatotoxicity in rats. Singh BK, Tripathi M, Chaudhari BP, et al. PLoS ONE 7(4), e34200, (2012)

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AML1-ETO mediates hematopoietic self-renewal and leukemogenesis through a COX/β-catenin signaling pathway. Zhang Y, Wang J, Wheat J, et al. Blood 121(24), 4906-16, (2013)

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Nimesulide is a selective COX-2 inhibitory, atypical non-steroidal anti-inflammatory drug. Suleyman H, Cadirci E, Albayrak A, et al. Curr. Med. Chem. 15(3), 278-83, (2008)

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Angiotensin 1-7 and Mas decrease thrombosis in Bdkrb2-/- mice by increasing NO and prostacyclin to reduce platelet spreading and glycoprotein VI activation. Fang C, Stavrou E, Schmaier AA, et al. Blood 121(15), 3023-32, (2013)

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Natural lipid nanoparticles containing nimesulide: synthesis, characterization and in vivo antiedematogenic and antinociceptive activities. Raffin RP, Lima A, Lorenzoni R, et al. J. Biomed. Nanotechnol. 8(2), 309-15, (2012)

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Nimesulide as a promising neuroprotectant in brain ischemia: new experimental evidences. Candelario-Jalil E Pharmacol. Res. 57(4), 266-73, (2008)

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Imidazolium ionic liquids as solvents of pharmaceuticals: influence on HSA binding and partition coefficient of nimesulide. Azevedo AM, Ribeiro DM, Pinto PC, et al. Int. J. Pharm. 443(1-2), 273-8, (2013)

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Nimesulide -- a multifactorial approach to inflammation and pain: scientific and clinical consensus. Rainsford KD Curr. Med. Res. Opin. 22(6), 1161-70, (2006)

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Prostaglandin E2 stimulates estradiol synthesis in the cerebellum postnatally with associated effects on Purkinje neuron dendritic arbor and electrophysiological properties. Dean SL, Wright CL, Hoffman JF, et al. Endocrinology 153(11), 5415-27, (2012)

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Radiation-induced non-targeted response in vivo: role of the TGFβ-TGFBR1-COX-2 signalling pathway. Chai Y, Lam RK, Calaf GM, et al. Br. J. Cancer 108(5), 1106-12, (2013)

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Nimesulide binding site in the B0AT1 (SLC6A19) amino acid transporter. Mechanism of inhibition revealed by proteoliposome transport assay and molecular modelling. Pochini L, Seidita A, Sensi C, et al. Biochem. Pharmacol. 89(3), 422-30, (2014)

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Mechanistic analysis of solute transport in an in vitro physiological two-phase dissolution apparatus. Mudie DM, Shi Y, Ping H, et al. Biopharm. Drug Dispos. 33(7), 378-402, (2012)

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The effect of guggulipid and nimesulide on MPTP-induced mediators of neuroinflammation in rat astrocytoma cells, C6. Niranjan R, Rajasekar N, Nath C, et al. Chem. Biol. Interact. 200(2-3), 73-83, (2012)

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Cyclooxygenase-1 inhibition attenuates angiotensin II-salt hypertension and neurogenic pressor activity in the rat. Asirvatham-Jeyaraj N, King AJ, Northcott CA, et al. Am. J. Physiol. Heart Circ. Physiol. 305(10), H1462-70, (2013)

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Induction of apoptosis and inhibition of cell proliferation by the cyclooxgenase enzyme blocker nimesulide in the Ishikawa endometrial cancer cell line. Özalp SS, Eren CY, Bostancıoğlu RB, et al. Eur. J. Obstet. Gynecol. Reprod. Biol. 164(1), 79-84, (2012)

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Breast ductal lavage for biomarker assessment in high risk women: rationale, design and methodology of a randomized phase II clinical trial with nimesulide, simvastatin and placebo. Lazzeroni M, Guerrieri-Gonzaga A, Serrano D, et al. BMC Cancer 12, 575, (2012)

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[Nimesulide: 25 years later]. Mattia C, Ciarcia S, Muhindo A, et al. Minerva Med. 101(4), 285-93, (2010)

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Nimesulide, a balanced drug for the treatment of osteoarthritis. Huskisson EC Clin. Exp. Rheumatol. 19(1 Suppl 22), S21-5, (2001)

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[Acute liver failure due to a treatment by nimesulide: another case and review]. Page M, Christin F, Hayi-Slayman D, et al. Ann. Fr. Anesth. Reanim. 27(9), 742-6, (2008)

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Nimesulide inhibited the growth of hypopharyngeal carcinoma cells via suppressing Survivin expression. Jia-Jun T, Su-Mei L, Liang Y, et al. Head Neck Oncol. 4, 7, (2012)

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Neuroprotective effect of allopurinol and nimesulide against cerebral ischemic reperfusion injury in diabetic rats. Ansari MA, Hussain SK, Mudagal MP, et al. Eur. Rev. Med. Pharmacol. Sci. 17(2), 170-8, (2013)

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Purification and characterization of the recombinant human prostaglandin H synthase-2 expressed in Pichia pastoris. Kukk K, Järving R, and Samel N Protein Expr. Purif. 83(2), 182-9, (2012)

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Quantification of nimesulide in human plasma by high-performance liquid chromatography with ultraviolet detector (HPLC-UV): application to pharmacokinetic studies in 28 healthy Korean subjects. Kim MS, Park YS, Kim SH, et al. J. Chromatogr. Sci. 50(5), 396-400, (2012)

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Development and validation of RP-HPLC method for simultaneous estimation of nimesulide, phenylephrine hydrochloride, chlorpheniramine maleate and caffeine anhydrous in pharmaceutical dosage form. Kumar A, Sharma R, Nair A, et al. Acta Pol. Pharm. 69(6), 1017-22, (2012)

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Nimesulide may be more efficient than allopurinol in protecting pancreas from acute ischemia/reperfusion injury in an animal model. Apostolidis D, Ntinas A, Kardassis D, et al. Vasc. Endovascular Surg. 46(8), 654-63, (2012)

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Formulation development of intermediate release Nimesulide tablets by CCRD for IVIVC studies. Hanif M, Shoaib MH, Yousuf RI, et al. Pak. J. Pharm. Sci. 27(4), 785-92, (2014)

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[Nimesulide]. Barskova VG, Eliseev MS, and Kudaeva FM Ter. Arkh. 79(8), 92-6, (2007)

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Introduction to "nimesulide: beyond COX-2". Warner TD Clin. Exp. Rheumatol. 19(1 Suppl 22), S1-2, (2001)

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Merck 14,6548

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