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MedKoo Cat#: 314273 | Name: Rofecoxib
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Description:

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

Rofecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that has now been withdrawn over safety concerns.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.

Chemical Structure

Rofecoxib
Rofecoxib
CAS#162011-90-7

Theoretical Analysis

MedKoo Cat#: 314273

Name: Rofecoxib

CAS#: 162011-90-7

Chemical Formula: C17H14O4S

Exact Mass: 314.0613

Molecular Weight: 314.36

Elemental Analysis: C, 64.95; H, 4.49; O, 20.36; S, 10.20

Price and Availability

Size Price Availability Quantity
250mg USD 150.00 Ready to ship
500mg USD 250.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 750.00 2 weeks
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Related CAS #
No Data
Synonym
MK966; MK966; MK 966; MK0966; MK0966; MK 0966; Rofecoxib; brand name: Vioxx; Ceoxx; Ceeoxx.
IUPAC/Chemical Name
4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
InChi Key
RZJQGNCSTQAWON-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1C(C2=CC=CC=C2)=C(C3=CC=C(S(=O)(C)=O)C=C3)CO1
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
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C22B06B02
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Rofecoxib is a potent, specific and orally active COX-2 inhibitor, with IC50s of 26 and 18 nM for human COX-2 in human osteosarcoma cells and Chinese hamster ovary cells, with a 1000-fold selectivity for COX-2 over human COX-1 (IC50 > 50 μM in U937 cells and > 15 μM in Chinese hamster ovary cells).
In vitro activity:
Rofecoxib significantly attenuated the separation of double strands of DNA (detected by increase the absorbance of DNA at 260 nm) induced by Cu ions. Rofecoxib significantly offered protection against UVB-induced DNA damage. It is concluded that rofecoxib offered protection against copper ions or UVB inducedDNA damage via different mechanisms not related to the inhibition COX-2. Reference: J Basic Clin Pharm. 2010 Dec;2(1):21-5. https://pubmed.ncbi.nlm.nih.gov/24825998/
In vivo activity:
To this end, Western blot analysis was carried out to measure the expression of COX-2, IL-1β, and TNF-α in the spinal cords of SOD1G93A mice. The results demonstrated that rofecoxib treatment clearly inhibited the expression of IL-1β and TNF-α by decreasing the protein expression of COX-2 in the spinal cords of SOD1G93A mice (Figures 6A,B). Taken together, our findings reveal that rofecoxib shows neuroprotective effects by targeting COX-2 proinflammatory signaling cascades in ALS mice. Reference: Front Neurosci. 2020 Aug 13;14:817. https://pubmed.ncbi.nlm.nih.gov/32903591/
Solvent mg/mL mM
Solubility
DMF 25.0 79.53
DMSO 40.4 128.65
Ethanol 0.1 0.32
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 314.36 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.

Recalculate based on batch purity %
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. Al-Nimer MS, Al-Deen SM, Abdul Lateef ZW. Rofecoxib prevents ctdsDNA against damage induced by copper sulfate and ultraviolet B radiation in vitro study. J Basic Clin Pharm. 2010 Dec;2(1):21-5. Epub 2011 Feb 15. PMID: 24825998; PMCID: PMC3979209. 2. Chan CC, Boyce S, Brideau C, Charleson S, Cromlish W, Ethier D, Evans J, Ford-Hutchinson AW, Forrest MJ, Gauthier JY, Gordon R, Gresser M, Guay J, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O'Neill GP, Ouellet M, Patrick D, Percival MD, Perrier H, Prasit P, Rodger I, et al. Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther. 1999 Aug;290(2):551-60. PMID: 10411562. 3. Zou YH, Guan PP, Zhang SQ, Guo YS, Wang P. Rofecoxib Attenuates the Pathogenesis of Amyotrophic Lateral Sclerosis by Alleviating Cyclooxygenase-2-Mediated Mechanisms. Front Neurosci. 2020 Aug 13;14:817. doi: 10.3389/fnins.2020.00817. PMID: 32903591; PMCID: PMC7438558. 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. PMID: 25472856.
In vitro protocol:
1. Al-Nimer MS, Al-Deen SM, Abdul Lateef ZW. Rofecoxib prevents ctdsDNA against damage induced by copper sulfate and ultraviolet B radiation in vitro study. J Basic Clin Pharm. 2010 Dec;2(1):21-5. Epub 2011 Feb 15. PMID: 24825998; PMCID: PMC3979209. 2. Chan CC, Boyce S, Brideau C, Charleson S, Cromlish W, Ethier D, Evans J, Ford-Hutchinson AW, Forrest MJ, Gauthier JY, Gordon R, Gresser M, Guay J, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O'Neill GP, Ouellet M, Patrick D, Percival MD, Perrier H, Prasit P, Rodger I, et al. Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther. 1999 Aug;290(2):551-60. PMID: 10411562.
In vivo protocol:
1. Zou YH, Guan PP, Zhang SQ, Guo YS, Wang P. Rofecoxib Attenuates the Pathogenesis of Amyotrophic Lateral Sclerosis by Alleviating Cyclooxygenase-2-Mediated Mechanisms. Front Neurosci. 2020 Aug 13;14:817. doi: 10.3389/fnins.2020.00817. PMID: 32903591; PMCID: PMC7438558. 2. 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. PMID: 25472856.
1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Rofecoxib. 2020 Mar 20. PMID: 31643940. 2: Hillson JL, Furst DE. Rofecoxib. Expert Opin Pharmacother. 2000 Jul;1(5):1053-66. doi: 10.1517/14656566.1.5.1053. PMID: 11249495. 3: Bombardier C, Laine L, Reicin A, Shapiro D, Burgos-Vargas R, Davis B, Day R, Ferraz MB, Hawkey CJ, Hochberg MC, Kvien TK, Schnitzer TJ; VIGOR Study Group. Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group. N Engl J Med. 2000 Nov 23;343(21):1520-8, 2 p following 1528. doi: 10.1056/NEJM200011233432103. PMID: 11087881. 4: Scott LJ, Lamb HM. Rofecoxib. Drugs. 1999 Sep;58(3):499-505; discussion 506-7. doi: 10.2165/00003495-199958030-00016. PMID: 10493277. 5: Garner SE, Fidan DD, Frankish R, Maxwell L. Rofecoxib for osteoarthritis. Cochrane Database Syst Rev. 2005 Jan 25;2005(1):CD005115. doi: 10.1002/14651858.CD005115. PMID: 15654705; PMCID: PMC8864971. 6: Matheson AJ, Figgitt DP. Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis. Drugs. 2001;61(6):833-65. doi: 10.2165/00003495-200161060-00019. PMID: 11398914. 7: Ahuja N, Singh A, Singh B. Rofecoxib: an update on physicochemical, pharmaceutical, pharmacodynamic and pharmacokinetic aspects. J Pharm Pharmacol. 2003 Jul;55(7):859-94. doi: 10.1211/0022357021387. PMID: 12906745. 8: Krymchantowski AV, Bigal ME. Rofecoxib in migraine. Expert Rev Neurother. 2005 Jan;5(1):55-61. doi: 10.1586/14737175.5.1.55. PMID: 15853474. 9: Weaver AL. Rofecoxib: clinical pharmacology and clinical experience. Clin Ther. 2001 Sep;23(9):1323-38. doi: 10.1016/s0149-2918(01)80112-0. PMID: 11589252. 10: Garner SE, Fidan DD, Frankish RR, Judd MG, Towheed TE, Wells G, Tugwell P. Rofecoxib for rheumatoid arthritis. Cochrane Database Syst Rev. 2005 Jan 25;2005(1):CD003685. doi: 10.1002/14651858.CD003685.pub2. PMID: 15674912; PMCID: PMC8725608. 11: 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. PMID: 25246044. 12: Burnier M. The safety of rofecoxib. Expert Opin Drug Saf. 2005 May;4(3):491-9. doi: 10.1517/14740338.4.3.491. PMID: 15934855. 13: Garner S, Fidan D, Frankish R, Judd M, Towheed T, Wells G, Tugwell P. Rofecoxib for the treatment of rheumatoid arthritis. Cochrane Database Syst Rev. 2002;(2):CD003685. doi: 10.1002/14651858.CD003685. Update in: Cochrane Database Syst Rev. 2002;(3):CD003685. doi: 10.1002/14651858.CD003685. PMID: 12076502. 14: Garner S, Fidan D, Frankish R, Judd M, Towheed T, Wells G, Tugwell P. Rofecoxib for the treatment of rheumatoid arthritis. Cochrane Database Syst Rev. 2002;(3):CD003685. doi: 10.1002/14651858.CD003685. Update in: Cochrane Database Syst Rev. 2005 Jan 25;(1):CD003685. doi: 10.1002/14651858.CD003685.pub2. PMID: 12137705. 15: Bulley S, Derry S, Moore RA, McQuay HJ. Single dose oral rofecoxib for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Oct 7;2009(4):CD004604. doi: 10.1002/14651858.CD004604.pub3. PMID: 19821329; PMCID: PMC4171390. 16: Sabolek M, Unrath A, Sperfeld AD, Connemann BJ, Kassubek J. Psychotische Störung unter Rofecoxib [Rofecoxib-induced psychosis]. Psychiatr Prax. 2007 May;34(4):200-2. German. doi: 10.1055/s-2006-940050. Epub 2006 Dec 7. PMID: 17160756. 17: Brenner GB, Makkos A, Nagy CT, Onódi Z, Sayour NV, Gergely TG, Kiss B, Görbe A, Sághy É, Zádori ZS, Lázár B, Baranyai T, Varga RS, Husti Z, Varró A, Tóthfalusi L, Schulz R, Baczkó I, Giricz Z, Ferdinandy P. Hidden Cardiotoxicity of Rofecoxib Can be Revealed in Experimental Models of Ischemia/Reperfusion. Cells. 2020 Feb 26;9(3):551. doi: 10.3390/cells9030551. PMID: 32111102; PMCID: PMC7140447. 18: Yang YR, Yang XF, Duan HC, Qiao JQ. Cyclooxygenase-2 inhibitor rofecoxib prevents chondrocytes against hypertrophy via Wnt/β-catenin pathway. J Biol Regul Homeost Agents. 2020 May-Jun;34(3):785-794. doi: 10.23812/20-78-A-8. PMID: 32723437. 19: Perry T, editor. Therapeutics Letter. Vancouver (BC): Therapeutics Initiative; 1994–. Letter 53, Rofecoxib (Vioxx®) withdrawal generates uncertainty about “ COX-2s”: Do product monographs adequately inform? 2004 Oct. PMID: 38620560. 20: Schmidt H, Woodcock BG, Geisslinger G. Benefit-risk assessment of rofecoxib in the treatment of osteoarthritis. Drug Saf. 2004;27(3):185-96. doi: 10.2165/00002018-200427030-00003. PMID: 14756580.