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                                    Structure of Nimesulide
                                    
                                    
CAS No.: 51803-78-2
                                    
                                
 
                                 
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                            The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Nimesulide is a COX2 selective inhibitor with IC50 of 26 μM.
Synonyms: R805
 
                
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        					 *For Research Use Only !
        				
        				*For Research Use Only !
        			
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Rybczynska, Malgorzata ; Sikorski, Artur ;
Abstract: The synthesis, spectral properties, thermal anal., structural characterization and in silico prediction of pharmacokinetic parameters of tetramethylammonium (compound 1) and tetraethylammonium (compound 2) salt of nimesulide were described in this article. Both compounds crystallize in the monoclinic P21/n space group, with one tetraalkylammonium cation and one nimesulide anion in the asym. unit and their crystal structures are stabilized by C-H···O hydrogen bonds between ions. Addnl., structures of title compounds are stabilized by π-π interactions (compound 1), or C-H···π interactions (compound 2) between nimesulide anions. The TG and DSC measurements show that compound 1 melts at a temperature higher than nimesulide, whereas the compound 2 melts at a temperature lower than nimesulide. The MALDI-TOF, 1H NMR, 13C NMR and ATR-FTIR analyses confirm the SCXRD study, that in compounds 1 and 2 nimesulide exists in an ionized form. Studies performed by SWISS ADME and ProTOX II tools, predict to be oral bioavailability of both salts obtained, and one of them (compound 1) is predicted to be well-absorbed by digestive system, while both compounds obtained are classified into toxicity class 4.
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                        | CAS No. : | 51803-78-2 | 
| Formula : | C13H12N2O5S | 
| M.W : | 308.31 | 
| SMILES Code : | CS(=O)(NC1=CC=C([N+]([O-])=O)C=C1OC2=CC=CC=C2)=O | 
| Synonyms : | 
                                R805
                             | 
| MDL No. : | MFCD00079470 | 
| InChI Key : | HYWYRSMBCFDLJT-UHFFFAOYSA-N | 
| Pubchem ID : | 4495 | 
| GHS Pictogram: |     | 
| Signal Word: | Danger | 
| Hazard Statements: | H301-H361 | 
| Precautionary Statements: | P501-P270-P202-P201-P264-P280-P308+P313-P301+P310+P330-P405 | 
| Class: | 6.1 | 
| UN#: | 2811 | 
| Packing Group: | Ⅲ | 
| Target | 
 | 
In Vitro:
| Cell Line | Concentration | Treated Time | Description | References | 
| Murine aortic smooth muscle cells | 0.1–1 µM | 48 hours | Nimesulide completely reversed the antimitogenic effect of APOE | J Clin Invest. 2004 Feb;113(4):609-18. | 
| Mouse tracheal smooth muscle cells | 1 μM | 10 minutes | To investigate the effect of nimesulide on SLIGRL-NH2-induced tracheal smooth muscle relaxation and PGE2 release, results showed that nimesulide significantly attenuated SLIGRL-NH2-induced relaxation and PGE2 release. | Br J Pharmacol. 2001 Jan;132(1):93-100. | 
In Vivo:
| Species | Animal Model | Administration | Dosage | Frequency | Description | References | 
| LDL receptor knockout mice | High-fat diet-induced atherosclerosis model | Drinking water administration | 40 mg/liter | 18 weeks | To evaluate the effect of nimesulide on atherosclerosis. Results showed that nimesulide inhibited COX-2 activity without affecting platelet function and did not significantly alter the progression of atherosclerosis. | Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3358-63 | 
| Mice | KrasG12D/+;Trp53−/− non-small-cell lung cancer graft model | Intraperitoneal injection | 5 mg/kg | Single dose | To evaluate the therapeutic effect of Nimesulide in combination with Bortezomib on Kras-driven non-small-cell lung cancer, results showed enhanced apoptotic response in tumor cells. | J Exp Med. 2018 Dec 3;215(12):3115-3135 | 
| Mice | Adult mouse brain neurogenesis model | Intraperitoneal injection | 10 mg/kg | Once daily for 5 days | Evaluate the effects of nimesulide on brain neurogenesis, results showed significant inhibition of progenitor cell proliferation in the SVZ | Br J Pharmacol. 2010 Mar;159(5):1118-25 | 
| Mice | EC-AMPK transgenic mice | Oral gavage | 25 mg/kg/day | Once daily for 4 weeks | Nimesulide significantly ameliorated arterial inflammation, steatohepatitis and hyperlipidaemia in EC-AMPK mice, without altering their blood pressure or clotting. | Br J Pharmacol. 2014 Jan;171(2):498-508 | 
Clinical Trial:
| NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations | 
| NCT02466581 | Rheumatoid Arthritis | Phase 4 | Recruiting | December 2021 | Sweden ... More >> Karolinska Institutet Recruiting Stockholm, Sweden, 171 76 Contact: Ronald van Vollenhoven, MD, prof +46(8)51776077 ronald.van.vollenhoven@ki.se Contact: Monica Ryden Aulin, PhD +46(8)51771110 monica.ryden.aulin@ki.se Less << | 
| NCT02563756 | Knee Osteoarthritis | Not Applicable | Recruiting | September 2022 | Sweden ... More >> Karolinska University Hospital Recruiting Stockholm, Sweden Contact: Carl Aulin, MD carl.aulin@karolinska.se Contact: Nicolas Martinez, MD +46709900089 nicolas.martinez-carranza@karolinska.se Less << | 
| NCT03104985 | - | Completed | - | - | |
| NCT02575274 | Peri-implantitis | Phase 2 Phase 3 | Unknown | July 2016 | Brazil ... More >> Federal University of Minas Gerais Belo Horizonte, Minas Gerais, Brazil, 30110031 Less << | 
| NCT03400462 | Temporomandibular Disorder | Not Applicable | Completed | - | - | 
| NCT03104985 | Trophic Ulcers ... More >> Chronic Venous Insufficiency Less << | Not Applicable | Completed | - | Russian Federation ... More >> Tula Municipal Clinical Hospital №2 Tula, Russian Federation, 300002 Less << | 
| NCT03616574 | Advanced or Metastatic Solid T... More >>umors Advanced or Metastatic Colorectal Cancer (mCRC) Less << | Phase 1 | Not yet recruiting | June 2021 | - | 
| NCT00932542 | Hemorrhoidectomy | Phase 2 Phase 3 | Unknown | November 2012 | Brazil ... More >> Clínica Reis Neto Campinas, São Paulo, Brazil, 13010-112 Less << | 
| NCT03119324 | Temporomandibular Joint Disord... More >>ers Less << | Not Applicable | Completed | - | - | 
| NCT01670552 | Acute and Chronic Inflammation... More >> Dyspepsia Less << | Phase 3 | Unknown | April 2017 | Brazil ... More >> Allegisa Recruiting Campinas, São Paulo, Brazil, 13.084-791 Contact: Pedro A. Petersen, MD +5519 3789-8610 alexandra@grupoinvestiga.com.br Contact: Alexandra F. Drumont, SC +5519 3789-8610 alexandra@grupoinvestiga.com.br Less << | 
| NCT01500577 | Breast Cancer | Phase 2 | Completed | - | Italy ... More >> European Institute of Oncology Milan, Italy Less << | 
| NCT02922712 | Knee Osteoarthritis | Phase 4 | Completed | - | - | 
| NCT01745614 | Pain | Phase 1 | Completed | - | - | 
| NCT01306708 | Adhesive Capsulitis | Phase 2 | Completed | - | Brazil ... More >> Universidade do Sul de Santa Catarina Tubarão, Santa Catarina, Brazil, 88704-900 Less << | 
| NCT02229747 | Pharyngitis | Phase 4 | Completed | - | - | 
| NCT01257126 | Upper Respiratory Tract Infect... More >>ions Less << | Phase 4 | Withdrawn | - | - | 
| NCT01609205 | Rheumatoid Arthritis | Phase 4 | Completed | - | Sweden ... More >> Linköping University Hospital Linköping, Sweden The karolinska Institute Stockholm, Sweden, 171 76 Less << | 
[2]Bernareggi A. Clinical pharmacokinetics of nimesulide. Clin Pharmacokinet. 1998 Oct;35(4):247-74.
Tags: Nimesulide | R805 | R 805 | R-805 | COX | Cyclooxygenase | COX inhibitor | COX-2 inhibitor | hepatotoxicity | 51803-78-2
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