Nimesulide
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MedKoo CAT#: 526073

CAS#: 51803-78-2

Description: Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with pain medication and fever reducing properties.


Chemical Structure

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Nimesulide
CAS# 51803-78-2

Theoretical Analysis

MedKoo Cat#: 526073
Name: Nimesulide
CAS#: 51803-78-2
Chemical Formula: C13H12N2O5S
Exact Mass: 308.05
Molecular Weight: 308.308
Elemental Analysis: C, 50.65; H, 3.92; N, 9.09; O, 25.95; S, 10.40

Price and Availability

Size Price Availability Quantity
1g USD 150
2g USD 250
5g USD 450
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Synonym: Nimesulide

IUPAC/Chemical Name: N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide

InChi Key: HYWYRSMBCFDLJT-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CS(=O)(NC1=CC=C([N+]([O-])=O)C=C1OC2=CC=CC=C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Nimesulide is a selective COX-2 inhibitor, with IC50s of 70 nM-70 μM in a time-dependent manner, but it shows no effect on COX-1 (IC50 >100 μM).
In vitro activity: Nimesulide (CAS 51803-78-2) has been shown to inhibit with high selectivity COX-2 without affecting COX-1 activity, so explaining the previous observations about the selectivity of the anti-prostaglandin effect of the drug. Nimesulide inhibited COX-2 activity in a concentration-dependent manner. In conclusion nimesulide's selective inhibitory effect on COX-2 is time-dependent whereas its weak effect on COX-1 is not time-dependent. Reference: Arzneimittelforschung. 1995 Oct;45(10):1096-8. https://pubmed.ncbi.nlm.nih.gov/8595067/
In vivo activity: The effects of nimesulide on lipopolysaccharide (LPS)-induced cerebrospinal prostaglandin E(2) (PGE(2)) and prostaglandin F(2alpha) (PGF(2alpha)) and on plasma tumor necrosis factor-alpha (TNF-alpha) levels were also evaluated. Nimesulide or indomethacin administered i.p 30 min prior LPS, IL-1beta, IL-6, TNF-alpha or arachidonic acid reduced the febrile response and PGE(2) or PGF(2alpha) levels in LPS-febrile rats but did not modify PGE(2)-induced fever. Nimesulide, but not indomethacin, reduced the fever induced by MIP-1alpha, PGF(2alpha), CRF or ET-1. Reference: Eur J Pharmacol. 2006 Aug 14;543(1-3):181-9. https://pubmed.ncbi.nlm.nih.gov/16814279/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 1.0 3.24

Preparing Stock Solutions

The following data is based on the product molecular weight 308.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Genç S, Attar E, Gürdöl F, Kendigelen S, Bilir A, Serdaroğlu H. The effect of COX-2 inhibitor, nimesulide, on angiogenetic factors in primary endometrial carcinoma cell culture. Clin Exp Med. 2007 Mar;7(1):6-10. doi: 10.1007/s10238-007-0119-x. PMID: 17380299. 2. Vago T, Bevilacqua M, Norbiato G. Effect of nimesulide action time dependence on selectivity towards prostaglandin G/H synthase/cyclooxygenase activity. Arzneimittelforschung. 1995 Oct;45(10):1096-8. PMID: 8595067. 3. Joharapurkar A, Kshirsagar S, Patel V, Patel M, Savsani H, Jain M. In vivo antidiabetic activity of nimesulide due to inhibition of amino acid transport. Basic Clin Pharmacol Toxicol. 2022 Jan;130(1):35-43. doi: 10.1111/bcpt.13670. Epub 2021 Oct 25. PMID: 34634192. 4. Werner MF, Souza GE, Zampronio AR. Nimesulide-induced antipyresis in rats involves both cyclooxygenase-dependent and independent mechanisms. Eur J Pharmacol. 2006 Aug 14;543(1-3):181-9. doi: 10.1016/j.ejphar.2006.05.029. Epub 2006 May 26. PMID: 16814279.
In vitro protocol: 1. Genç S, Attar E, Gürdöl F, Kendigelen S, Bilir A, Serdaroğlu H. The effect of COX-2 inhibitor, nimesulide, on angiogenetic factors in primary endometrial carcinoma cell culture. Clin Exp Med. 2007 Mar;7(1):6-10. doi: 10.1007/s10238-007-0119-x. PMID: 17380299. 2. Vago T, Bevilacqua M, Norbiato G. Effect of nimesulide action time dependence on selectivity towards prostaglandin G/H synthase/cyclooxygenase activity. Arzneimittelforschung. 1995 Oct;45(10):1096-8. PMID: 8595067.
In vivo protocol: 1. Joharapurkar A, Kshirsagar S, Patel V, Patel M, Savsani H, Jain M. In vivo antidiabetic activity of nimesulide due to inhibition of amino acid transport. Basic Clin Pharmacol Toxicol. 2022 Jan;130(1):35-43. doi: 10.1111/bcpt.13670. Epub 2021 Oct 25. PMID: 34634192. 2. Werner MF, Souza GE, Zampronio AR. Nimesulide-induced antipyresis in rats involves both cyclooxygenase-dependent and independent mechanisms. Eur J Pharmacol. 2006 Aug 14;543(1-3):181-9. doi: 10.1016/j.ejphar.2006.05.029. Epub 2006 May 26. PMID: 16814279.

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1: Sharma R, Bali A, Chaudhari BB. Synthesis of methanesulphonamido-benzimidazole derivatives as gastro-sparing antiinflammatory agents with antioxidant effect. Bioorg Med Chem Lett. 2017 Jul 1;27(13):3007-3013. doi: 10.1016/j.bmcl.2017.05.017. Epub 2017 May 6. PubMed PMID: 28512025.

2: Barrio M, Huguet J, Robert B, Rietveld IB, Céolin R, Tamarit JL. Pressure-temperature phase diagram of the dimorphism of the anti-inflammatory drug nimesulide. Int J Pharm. 2017 Jun 15;525(1):54-59. doi: 10.1016/j.ijpharm.2017.04.016. Epub 2017 Apr 12. PubMed PMID: 28411142.

3: Jian YS, Chen CW, Lin CA, Yu HP, Lin HY, Liao MY, Wu SH, Lin YF, Lai PS. Hyaluronic acid-nimesulide conjugates as anticancer drugs against CD44-overexpressing HT-29 colorectal cancer in vitro and in vivo. Int J Nanomedicine. 2017 Mar 27;12:2315-2333. doi: 10.2147/IJN.S120847. eCollection 2017. PubMed PMID: 28392690; PubMed Central PMCID: PMC5376212.

4: Zhang HT, Tian M, He QW, Chi N, Xiu CM, Wang YB. Effect of Aster tataricus on production of inflammatory mediators in LPS stimulated rat astrocytoma cell line (C6) and THP-1 cells. Saudi Pharm J. 2017 Mar;25(3):370-375. doi: 10.1016/j.jsps.2016.09.001. Epub 2016 Sep 14. PubMed PMID: 28344491; PubMed Central PMCID: PMC5357093.

5: Diniz MC, Olivon VC, Tavares LD, Simplicio JA, Gonzaga NA, de Souza DG, Bendhack LM, Tirapelli CR, Bonaventura D. Mechanisms underlying sodium nitroprusside-induced tolerance in the mouse aorta: Role of ROS and cyclooxygenase-derived prostanoids. Life Sci. 2017 May 1;176:26-34. doi: 10.1016/j.lfs.2017.03.016. Epub 2017 Mar 21. PubMed PMID: 28341178.

6: Singh B, Mourya A, Sah SP, Kumar A. Protective effect of losartan and ramipril against stress induced insulin resistance and related complications: Anti-inflammatory mechanisms. Eur J Pharmacol. 2017 Apr 15;801:54-61. doi: 10.1016/j.ejphar.2017.02.050. Epub 2017 Mar 1. PubMed PMID: 28259714.

7: Mozolewski P, Moskot M, Jakóbkiewicz-Banecka J, Węgrzyn G, Bocheńska K, Banecki B, Gabig-Cimińska M. Nonsteroidal anti-inflammatory drugs modulate cellular glycosaminoglycan synthesis by affecting EGFR and PI3K signaling pathways. Sci Rep. 2017 Feb 27;7:43154. doi: 10.1038/srep43154. PubMed PMID: 28240227; PubMed Central PMCID: PMC5327420.

8: Zhou L, Pang X, Jiang J, Zhong D, Chen X. Nimesulide and 4'-Hydroxynimesulide as Bile Acid Transporters Inhibitors Are Contributory Factors for Drug-Induced Cholestasis. Drug Metab Dispos. 2017 May;45(5):441-448. doi: 10.1124/dmd.116.074104. Epub 2017 Feb 15. PubMed PMID: 28202577.

9: Nagulakonda NNM, Ananthula RS, Susarla KPC, Krishnamurthy T, Gollapalli NR. Quantification and In Silico Toxicity Assessment of Nimesulide and its Related Substances. J Chromatogr Sci. 2017 May 1;55(5):508-517. doi: 10.1093/chromsci/bmx003. PubMed PMID: 28168284.

10: Kim EC, Toyono T, Berlinicke CA, Zack DJ, Jurkunas U, Usui T, Jun AS. Screening and Characterization of Drugs That Protect Corneal Endothelial Cells Against Unfolded Protein Response and Oxidative Stress. Invest Ophthalmol Vis Sci. 2017 Feb 1;58(2):892-900. doi: 10.1167/iovs.16-20147. PubMed PMID: 28159976; PubMed Central PMCID: PMC5295784.

11: Mareddy J, Suresh N, Kumar CG, Kapavarapu R, Jayasree A, Pal S. 1,2,3-Triazole-nimesulide hybrid: Their design, synthesis and evaluation as potential anticancer agents. Bioorg Med Chem Lett. 2017 Feb 1;27(3):518-523. doi: 10.1016/j.bmcl.2016.12.030. Epub 2016 Dec 10. PubMed PMID: 28011214.

12: Martínez LM, Videa M, Sosa NG, Ramírez JH, Castro S. Long-Term Stability of New Co-Amorphous Drug Binary Systems: Study of Glass Transitions as a Function of Composition and Shelf Time. Molecules. 2016 Dec 14;21(12). pii: E1712. PubMed PMID: 27983640.

13: de Matos RF, Mendonça LC, da Silva Souza KG, Fonseca AA, Costa EM, de Lima MV, Vieira JM, de Brito MT, Monteiro MC. Nimesulide inhibits pathogenic fungi: PGE2-dependent mechanisms. Folia Microbiol (Praha). 2017 Mar;62(2):169-174. doi: 10.1007/s12223-016-0483-6. Epub 2016 Nov 19. PubMed PMID: 27866353.

14: Barbalho JC, Vasconcellos RJ, de Morais HH, Santos LA, Almeida RA, Rêbelo HL, Lucena EE, de Araújo SQ. Effects of co-administered dexamethasone and nimesulide on pain, swelling, and trismus following third molar surgery: a randomized, triple-blind, controlled clinical trial. Int J Oral Maxillofac Surg. 2017 Feb;46(2):236-242. doi: 10.1016/j.ijom.2016.10.011. Epub 2016 Nov 16. PubMed PMID: 27865630.

15: Abueid L, Uslu Ü, Cumbul A, Velioğlu Öğünç A, Ercan F, Alican İ. Inhibition of 5-lipoxygenase by zileuton in a rat model of myocardial infarction. Anatol J Cardiol. 2016 Nov 10. doi: 10.14744/AnatolJCardiol.2016.7248. [Epub ahead of print] PubMed PMID: 27849187.

16: Shah RM, Eldridge DS, Palombo EA, Harding IH. Microwave-assisted formulation of solid lipid nanoparticles loaded with non-steroidal anti-inflammatory drugs. Int J Pharm. 2016 Dec 30;515(1-2):543-554. doi: 10.1016/j.ijpharm.2016.10.054. Epub 2016 Oct 24. PubMed PMID: 27789371.

17: Arslan A, Ozcicek A, Suleyman B, Coban TA, Cimen FK, Nalkiran HS, Kuzucu M, Altuner D, Cetin N, Suleyman H. Effects of nimesulide on the small intestine mucositis induced by methotrexate in rats. Exp Anim. 2016 Nov 1;65(4):329-336. Epub 2016 Jun 21. PubMed PMID: 27333839; PubMed Central PMCID: PMC5111835.

18: Mezzelani M, Gorbi S, Fattorini D, d'Errico G, Benedetti M, Milan M, Bargelloni L, Regoli F. Transcriptional and cellular effects of Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) in experimentally exposed mussels, Mytilus galloprovincialis. Aquat Toxicol. 2016 Nov;180:306-319. doi: 10.1016/j.aquatox.2016.10.006. Epub 2016 Oct 11. PubMed PMID: 27776296.

19: Lima JB, Veloso CC, Vilela FC, Giusti-Paiva A. Prostaglandins mediate zymosan-induced sickness behavior in mice. J Physiol Sci. 2016 Oct 3. [Epub ahead of print] PubMed PMID: 27699583.

20: Hoffman JF, Wright CL, McCarthy MM. A Critical Period in Purkinje Cell Development Is Mediated by Local Estradiol Synthesis, Disrupted by Inflammation, and Has Enduring Consequences Only for Males. J Neurosci. 2016 Sep 28;36(39):10039-49. doi: 10.1523/JNEUROSCI.1262-16.2016. Epub 2016 Sep 28. PubMed PMID: 27683901; PubMed Central PMCID: PMC5039254.