Rofecoxib
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Hodoodo CAT#: H314273

CAS#: 162011-90-7

Description: Rofecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that has now been withdrawn over safety concerns.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

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Rofecoxib
CAS# 162011-90-7

Theoretical Analysis

Hodoodo Cat#: H314273
Name: Rofecoxib
CAS#: 162011-90-7
Chemical Formula: C17H14O4S
Exact Mass: 314.06
Molecular Weight: 314.360
Elemental Analysis: C, 64.95; H, 4.49; O, 20.36; S, 10.20

Price and Availability

Size Price Availability Quantity
250mg USD 150 Ready to ship
500mg USD 250 Ready to ship
1g USD 450 Ready to ship
2g USD 750
5g USD 1550
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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:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 79.53
DMSO 40.4 128.65
Ethanol 0.1 0.32

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.

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 1: Rahme E, Roussy JP, Lafrance JP, Nedjar H, Morin S. Use of nonsteroidal antiinflammatory drugs: is there a change in patient risk profile after withdrawal of rofecoxib? J Rheumatol. 2011 Feb;38(2):195-202. doi: 10.3899/jrheum.100332. Epub 2010 Nov 15. Review. PubMed PMID: 21078717.

2: 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;(4):CD004604. doi: 10.1002/14651858.CD004604.pub3. Review. PubMed PMID: 19821329; PubMed Central PMCID: PMC4171390.

3: Jaksch W, Dejaco C, Schirmer M. 4 years after withdrawal of rofecoxib: where do we stand today? Rheumatol Int. 2008 Oct;28(12):1187-95. doi: 10.1007/s00296-008-0650-4. Epub 2008 Jul 29. Review. PubMed PMID: 18663451.

4: Chen YF, Jobanputra P, Barton P, Bryan S, Fry-Smith A, Harris G, Taylor RS. Cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs (etodolac, meloxicam, celecoxib, rofecoxib, etoricoxib, valdecoxib and lumiracoxib) for osteoarthritis and rheumatoid arthritis: a systematic review and economic evaluation. Health Technol Assess. 2008 Apr;12(11):1-278, iii. Review. PubMed PMID: 18405470.

5: Mason RP, Walter MF, Day CA, Jacob RF. A biological rationale for the cardiotoxic effects of rofecoxib: comparative analysis with other COX-2 selective agents and NSAids. Subcell Biochem. 2007;42:175-90. Review. PubMed PMID: 17612051.

6: Burnier M. The safety of rofecoxib. Expert Opin Drug Saf. 2005 May;4(3):491-9. Review. PubMed PMID: 15934855.

7: Krymchantowski AV, Bigal ME. Rofecoxib in migraine. Expert Rev Neurother. 2005 Jan;5(1):55-61. Review. PubMed PMID: 15853474.

8: Marshall LL. Angioedema associated with aspirin and rofecoxib. Ann Pharmacother. 2005 May;39(5):944-8. Epub 2005 Apr 5. Review. PubMed PMID: 15811906.

9: Barden J, Edwards J, Moore RA, McQuay HJ. Single dose oral rofecoxib for postoperative pain. Cochrane Database Syst Rev. 2005 Jan 25;(1):CD004604. Review. Update in: Cochrane Database Syst Rev. 2009;(4):CD004604. PubMed PMID: 15674955.

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;(1):CD003685. Review. PubMed PMID: 15674912.

11: Garner SE, Fidan DD, Frankish R, Maxwell L. Rofecoxib for osteoarthritis. Cochrane Database Syst Rev. 2005 Jan 25;(1):CD005115. Review. PubMed PMID: 15654705.

12: Scheen AJ. [Withdrawal of rofecoxib (Vioxx): what about cardiovascular safety of COX-2 selective non-steroidal anti-inflammatory drugs?]. Rev Med Liege. 2004 Oct;59(10):565-9. Review. French. PubMed PMID: 15623076.

13: Lizán Tudela L, Magaz Marqués S, Varela Moreno C, Riesgo Bucher Y. [Analysis of cost-minimization treatment with paracetamol or COX-2 inhibitors (rofecoxib) for pain from arthrosis of the knee or hip]. Aten Primaria. 2004 Dec;34(10):534-40. Review. Spanish. PubMed PMID: 15607056.

14: Szalat A, Krasilnikov I, Bloch A, Meir K, Rubinger D, Mevorach D. Acute renal failure and interstitial nephritis in a patient treated with rofecoxib: case report and review of the literature. Arthritis Rheum. 2004 Aug 15;51(4):670-3. Review. PubMed PMID: 15334443.

15: Barden J, Edwards J, Moore RA, McQuay HJ. Single dose oral rofecoxib for postoperative pain. Cochrane Database Syst Rev. 2004;(1):CD004604. Review. Update in: Cochrane Database Syst Rev. 2005;(1):CD004604. PubMed PMID: 14974074.

16: Schmidt H, Woodcock BG, Geisslinger G. Benefit-risk assessment of rofecoxib in the treatment of osteoarthritis. Drug Saf. 2004;27(3):185-96. Review. PubMed PMID: 14756580.

17: Phelan KM, Mosholder AD, Lu S. Lithium interaction with the cyclooxygenase 2 inhibitors rofecoxib and celecoxib and other nonsteroidal anti-inflammatory drugs. J Clin Psychiatry. 2003 Nov;64(11):1328-34. Review. PubMed PMID: 14658947.

18: Coulter DM, Clark DW, Savage RL. Celecoxib, rofecoxib, and acute temporary visual impairment. BMJ. 2003 Nov 22;327(7425):1214-5. Review. PubMed PMID: 14630760; PubMed Central PMCID: PMC274063.

19: Weir MR, Sperling RS, Reicin A, Gertz BJ. Selective COX-2 inhibition and cardiovascular effects: a review of the rofecoxib development program. Am Heart J. 2003 Oct;146(4):591-604. Review. PubMed PMID: 14564311.

20: 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. Review. PubMed PMID: 12906745.