Rofecoxib

  • CAT Number: A000271
  • CAS Number: 162011-90-7
  • Molecular Formula: C₁₇H₁₄O₄S
  • Molecular Weight: 314.36
  • Purity: ≥95%
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Rofecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that has now been withdrawn over safety concerns. Rofecoxib exhibits anti-inflammatory, analgesic, and antipyretic activities in animal models. The mechanism of action of rofecoxib is believed to be due to inhibition of prostaglandin synthesis, via inhibition of cyclooxygenase-2 (COX-2). At therapeutic concentrations in humans, rofecoxib does not inhibit the cyclooxygenase-1 (COX-1) isoenzyme. Studies to elucidate the mechanism of action of fofecoxib in the acute treatment of migraine have not been conducted.

Catalog Number A000271
CAS Number 162011-90-7
Synonyms

Vioxx; 162011-90-7; Ceoxx; MK 966; 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one

Molecular Formula

C₁₇H₁₄O₄S

Purity 95%
Target COX
Solubility Soluble in DMSO > 10 mM
Storage -20°C
InChI InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChIKey RZJQGNCSTQAWON-UHFFFAOYSA-N
SMILES CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
Reference

1: Gaukler SM, Ruff JS, Morrison LC, Potts W. Rofecoxib-Induced Deleterious
Effects Escape Detection by Organismal Performance Assays. J Pharm Negat Results.
2016;7(1):4-11. doi: 10.4103/0976-9234.177051. Epub 2016 Feb 19. PubMed PMID:
28042224; PubMed Central PMCID: PMC5199028.
<br>

2: Orlando BJ, Malkowski MG. Crystal structure of rofecoxib bound to human
cyclooxygenase-2. Acta Crystallogr F Struct Biol Commun. 2016 Oct 1;72(Pt
10):772-776. Epub 2016 Sep 22. PubMed PMID: 27710942; PubMed Central PMCID:
PMC5053162.

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3: Wang H, Meng F. Molecular simulation study on concentration effects of
rofecoxib with POPC bilayer. J Mol Graph Model. 2016 Nov;70:94-99. doi:
10.1016/j.jmgm.2016.09.012. Epub 2016 Sep 23. PubMed PMID: 27693948.

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4: Liu NN, Sun YZ, Zhao N, Chen L. Rofecoxib inhibits retinal neovascularization
via down regulation of cyclooxygenase-2 and vascular endothelial growth factor
expression. Clin Exp Ophthalmol. 2015 Jul;43(5):458-65. doi: 10.1111/ceo.12473.
Epub 2015 Jan 15. PubMed PMID: 25472856.

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5: Goy J, Paikin J, Crowther M. Rofecoxib does not appear to increase the risk of
venous thromboembolism: a systematic review of the literature. Thromb Res. 2014
Nov;134(5):997-1003. doi: 10.1016/j.thromres.2014.08.030. Epub 2014 Sep 16.
Review. PubMed PMID: 25246044.
<br>

6: Vadlamudi HC, Raju YP, Asuntha G, Nair R, Murthy KV, Vulava J. Assessment of
hupu gum for its carrier property in the design and evaluation of solid mixtures
of poorly water soluble drug – rofecoxib. Curr Drug Deliv. 2014;11(1):62-71.
PubMed PMID: 24783235.
<br>

7: Yamakawa N, Suzuki K, Yamashita Y, Katsu T, Hanaya K, Shoji M, Sugai T,
Mizushima T. Structure-activity relationship of celecoxib and rofecoxib for the
membrane permeabilizing activity. Bioorg Med Chem. 2014 Apr 15;22(8):2529-34.
doi: 10.1016/j.bmc.2014.02.032. Epub 2014 Mar 12. PubMed PMID: 24650702.
<br>

8: Graham DY, Jewell NP, Chan FK. Rofecoxib and Clinically Significant
Gastrointestinal Events: Response. Am J Med Sci. 2014 Feb 19. [Epub ahead of
print] PubMed PMID: 24556931.
<br>

9: A Wahab I, Pratt NL, Kalisch LM, Roughead EE. Comparing time to adverse drug
reaction signals in a spontaneous reporting database and a claims database: a
case study of rofecoxib-induced myocardial infarction and rosiglitazone-induced
heart failure signals in Australia. Drug Saf. 2014 Jan;37(1):53-64. doi:
10.1007/s40264-013-0124-9. PubMed PMID: 24242213.
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10: Miyajima A, Okamoto M, Muto T, Hirota T. Disruption of elastic lamellae in
aorta and dysfunction of vaso-regulation by rofecoxib in rats. J Toxicol Sci.
2013;38(5):719-29. PubMed PMID: 24025789.

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