Nimesulide | CAS#51803-78-2

MedKoo Cat#: 526073 | Name: Nimesulide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Nimesulide

CAS#51803-78-2

Theoretical Analysis

MedKoo Cat#: 526073

Name: Nimesulide

CAS#: 51803-78-2

Chemical Formula: C13H12N2O5S

Exact Mass: 308.0467

Molecular Weight: 308.31

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 150.00
2g	USD 250.00
5g	USD 450.00

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Related CAS #

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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

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Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM	comments
Solubility
	Ethanol	1.0	3.24

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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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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. 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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.