Nimesulide-d5 | CAS#1330180-22-7 | nimesulide quantification internal standard

MedKoo Cat#: 464481 | Name: Nimesulide-d5

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Description:

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

Nimesulide-d5 is intended for use as an internal standard for the quantification of nimesulide by GC- or LC-MS. Nimesulide is a non-steroidal anti-inflammatory drug (NSAID) and COX-2 inhibitor (IC50s = 1.27 and 0.03 µM for the human and ovine enzymes, respectively). It is selective for COX-2 over COX-1 (IC50s = 70 and 22 µM for the human and ovine enzymes, respectively). Nimesulide also inhibits sodium-dependent neutral amino acid transporter (B0AT1) with an IC50 value of 23 µM for the rat kidney transporter. It inhibits infection-induced increases in brain prostaglandin E2 (PGE2; Item No. 14010) levels, as well as reduces pyresis (ED50 = 0.3 mg/kg), in yeast-infected rats. Nimesulide (2.9 mg/kg) inhibits formalin-induced hindpaw thermal hyperalgesia in rats.

Chemical Structure

Nimesulide-d5

CAS#1330180-22-7

Theoretical Analysis

MedKoo Cat#: 464481

Name: Nimesulide-d5

CAS#: 1330180-22-7

Chemical Formula: C13H7D5N2O5S

Exact Mass: 313.0781

Molecular Weight: 313.34

Elemental Analysis: C, 49.83; H, 5.47; N, 8.94; O, 25.53; S, 10.23

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Synonym

Nimesulide-d5; Nimesulide d5; R805-d5; R805 d5; R 805-d5; R-805-d5;

IUPAC/Chemical Name

N-(4-nitro-2-(phenoxy-d5)phenyl)methanesulfonamide

InChi Key

HYWYRSMBCFDLJT-VIQYUKPQSA-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/i2D,3D,4D,5D,6D

SMILES Code

CS(NC1=C(OC2=C(C([2H])=C(C([2H])=C2[2H])[2H])[2H])C=C([N+]([O-])=O)C=C1)(=O)=O

Appearance

Solid powder

Purity

>99% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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-d5 is a deuterium labeled Nimesulide. Nimesulide is a selective COX-2 inhibitor.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 313.34 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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