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Celecoxib

Celecoxib

  • CAT Number: A001201
  • CAS Number: 169590-42-5
  • Molecular Formula: C₁₇H₁₄F₃N₃O₂S
  • Molecular Weight: 381.37
  • Purity: ≥95%
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Celecoxib was developed by G. D. Searle & Company and co-promoted by Monsanto Company (parent company of Searle) and Pfizer under the brand name Celebrex. Monsanto merged with Pharmacia, from which the Medical Research Division was acquired by Pfizer, giving Pfizer ownership of Celebrex. The drug was at the core of a major patent dispute that was resolved in Searle/’s favor (later Pfizer) in 2004. In University of Rochester v. G.D. Searle & Co., 358 F.3d 916 (Fed. Cir. 2004), the University of Rochester claimed that United States Pat. No. 6,048,850 (which claimed a method of inhibiting COX-2 in humans using a compound, without actually disclosing what that compound might be) covered drugs such as celecoxib. The court ruled in favor of Searle, holding in essence that the University had claimed a method requiring, yet provided no written description of, a compound that could inhibit COX-2 and therefore the patent was invalid.

Catalog Number A001201
CAS Number 169590-42-5
Molecular Formula

C₁₇H₁₄F₃N₃O₂S

Purity 95%
Target COX
Solubility >19.1mg/mL in DMSO
Storage 3 years -20C powder
InChI InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChIKey RZEKVGVHFLEQIL-UHFFFAOYSA-N
SMILES CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
Reference

</br>1:Combination of celecoxib and PD184161 exerts synergistic inhibitory effects on gallbladder cancer cell proliferation. Deng M, Qin Y, Chen X, Li D, Wang Q, Zheng H, Gu L, Deng C, Xue Y, Zhu D, Wang Q, Wang J.Oncol Lett. 2017 May;13(5):3850-3858. doi: 10.3892/ol.2017.5914. Epub 2017 Mar 27. PMID: 28521485 </br>2:Celecoxib Therapy and <i>CYP2C9</i> Genotype. Dean L.In: Pratt V, McLeod H, Dean L, Malheiro A, Rubinstein W, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-.2016 Aug 18. PMID: 28520369 Free Books & Documents</br>3:Phase III Randomized, Placebo-Controlled, Double-Blind Trial of Celecoxib in Addition to Standard Chemotherapy for Advanced Non-Small-Cell Lung Cancer With Cyclooxygenase-2 Overexpression: CALGB 30801 (Alliance). Edelman MJ, Wang X, Hodgson L, Cheney RT, Baggstrom MQ, Thomas SP, Gajra A, Bertino E, Reckamp KL, Molina J, Schiller JH, Mitchell-Richards K, Friedman PN, Ritter J, Milne G, Hahn OM, Stinchcombe TE, Vokes EE; Alliance for Clinical Trials in Oncology..J Clin Oncol. 2017 May 10:JCO2016713743. doi: 10.1200/JCO.2016.71.3743. [Epub ahead of print] PMID: 28489511 </br>4:Combined application of diclofenac and celecoxib with an opioid yields superior efficacy in metastatic bone cancer pain: a randomized controlled trial. Liu Z, Xu Y, Liu ZL, Tian YZ, Shen XH.Int J Clin Oncol. 2017 May 8. doi: 10.1007/s10147-017-1133-y. [Epub ahead of print] PMID: 28484877 </br>5:The influence of CYP2C19 polymorphisms on exacerbating effect of rabeprazole in celecoxib-induced small bowel injury. Nuki Y, Umeno J, Washio E, Maehata Y, Hirano A, Miyazaki M, Kobayashi H, Kitazono T, Matsumoto T, Esaki M.Aliment Pharmacol Ther. 2017 May 8. doi: 10.1111/apt.14134. [Epub ahead of print] PMID: 28481007 </br>6:Preemptive analgesia by using celecoxib combined with tramadol/APAP alleviates post-operative pain of patients undergoing total knee arthroplasty. Xu Z, Zhang H, Luo J, Zhou A, Zhang J.Phys Sportsmed. 2017 May 17:1-7. doi: 10.1080/00913847.2017.1325312. [Epub ahead of print] PMID: 28475475 </br>7:Therapy: Celecoxib reduces risk of ulcer bleeding. Onuora S.Nat Rev Rheumatol. 2017 May 4. doi: 10.1038/nrrheum.2017.63. [Epub ahead of print] No abstract available. PMID: 28469268 </br>8:Celecoxib Alleviates Memory Deficits by Downregulation of COX-2 Expression and Upregulation of the BDNF-TrkB Signaling Pathway in a Diabetic Rat Model. Yang Y, Gao L.J Mol Neurosci. 2017 May 2. doi: 10.1007/s12031-017-0922-0. [Epub ahead of print] PMID: 28466254 </br>9:The ErbB family and androgen receptor signaling are targets of Celecoxib in prostate cancer. Brizzolara A, Benelli R, Venè R, Barboro P, Poggi A, Tosetti F, Ferrari N.Cancer Lett. 2017 Apr 25;400:9-17. doi: 10.1016/j.canlet.2017.04.025. [Epub ahead of print] PMID: 28450158 </br>10:Adjunctive celecoxib for schizophrenia: A meta-analysis of randomized, double-blind, placebo-controlled trials. Zheng W, Cai DB, Yang XH, Ungvari GS, Ng CH, Müller N, Ning YP, Xiang YT.J Psychiatr Res. 2017 Apr 14;92:139-146. doi: 10.1016/j.jpsychires.2017.04.004. [Epub ahead of print] PMID: 28445800

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