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

MedKoo CAT#: 200700

CAS#: 169590-42-5

Description: 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.


Price and Availability

Size
Price

50mg
USD 120
500mg
USD 450
10g
Ask price
Size
Price

100mg
USD 150
1g
USD 550
20g
Ask price
Size
Price

200mg
USD 250
5g
USD 850

Celecoxib, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200700
Name: Celecoxib
CAS#: 169590-42-5
Chemical Formula: C17H14F3N3O2S
Exact Mass: 381.07588
Molecular Weight: 381.37
Elemental Analysis: C, 53.54; H, 3.70; F, 14.94; N, 11.02; O, 8.39; S, 8.41


Synonym:

IUPAC/Chemical Name: 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide

InChi Key: RZEKVGVHFLEQIL-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=S(C1=CC=C(N2N=C(C(F)(F)F)C=C2C3=CC=C(C)C=C3)C=C1)(N)=O


Technical Data

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, not in water

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

Celecoxib is a sulfa non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer. It is known under the brand name Celebrex or Celebra for arthritis and Onsenal for polyps. Celecoxib is available by prescription in capsule form.
 
Pfizer sells celecoxib under the brand name Celebrex. Celecoxib is not currently available as a generic in the United States, because the intellectual property is still controlled by Pfizer. However, in other countries, including India and the Philippines, it is legally available as a generic under the brand names Cobix and Celcoxx. XL Laboratories sells celecoxib under the brand name Selecap in Vietnam and the Philippines. See http://en.wikipedia.org/wiki/Celecoxib .
 
History
After the withdrawal of rofecoxib (Vioxx) from the market in September 2004, Celebrex enjoyed a robust increase in sales. However, the results of the APC trial in December of that year raised concerns that Celebrex might carry risks similar to those of Vioxx, and Pfizer announced a moratorium on direct-to-consumer advertising of Celebrex soon afterwards. After a significant drop, sales of Celebrex have recovered, and reached $2 billion in 2006.  Pfizer resumed advertising Celebrex in magazines in 2006,  and resumed television advertising in April 2007 with an unorthodox, 2Å“ minute advertisement which extensively discussed the adverse effects of Celebrex in comparison with other anti-inflammatory drugs. The ad drew criticism from the consumer advocacy group Public Citizen, which called the ad's comparisons misleading. Pfizer has responded to Public Citizen's concerns with assurances that they are truthfully advertising the risk and benefits of Celebrex as set forth by the FDA. In late 2007, Pfizer released another U.S. television ad for Celebrex, which also discussed celecoxib's adverse effects in comparison with those of other anti-inflammatory drugs. Dr. Simmons of Brigham Young University, who discovered the COX-2 enzyme, is suing Pfizer to be credited with discovery of the technique in 1989 that eventually led to the drug, and for $1 billion USD, (The company has made about $30 billion from the drug as of 2006).
Research into cancer prevention
The role that celecoxib might have in reducing the rates of certain cancers has been the subject of many studies. However, given the side effects of anti-COX-2 on rates of heart disease, there is no current medical recommendation to use this drug for cancer reduction. Colorectal cancer risk is clearly reduced in people regularly taking a NSAID like aspirin or celecoxib. In addition, some epidemiological studies, and most preclinical studies pointed out that specific COX-2 inhibitors like celecoxib are more potent and less toxic than "older" NSAIDs. Twelve carcinogenesis studies support that celecoxib is strikingly potent to prevent intestinal cancer in rats or mice (data available on the Chemoprevention Database). Small-scale clinical trials in very high risk people (belonging to FAP families) also indicate that celecoxib can prevent polyp growth. Hence large-scale randomized clinical trials were undertaken and results published by N. Arber and M. Bertagnolli in the New England Journal of Medicine, August 2006. Results show a 33 to 45% polyp recurrence reduction in people taking 400–800 mg celecoxib each day. However, serious cardiovascular events were significantly more frequent in the celecoxib-treated groups (see above, cardiovascular toxicity). Aspirin shows a similar (and possibly larger) protective effect, has demonstrated cardioprotective effects and is significantly cheaper, but there have been no head-to-head clinical trials comparing the two drugs.
 
Research into cancer treatment
Different from cancer prevention, cancer treatment is focused on the therapy of tumors that have already formed and have established themselves inside the patient. Many studies are ongoing to determine whether celecoxib might be useful for this latter condition. However, during molecular studies in the laboratory, it became apparent that celecoxib could interact with other intracellular components besides its most famous target, cyclooxygenase 2 (COX-2). The discovery of these additional targets has generated much controversy, and the initial assumption that celecoxib reduces tumor growth primarily via the inhibition of COX-2 became contentious. Certainly, the inhibition of COX-2 is paramount for the anti-inflammatory and analgesic function of celecoxib. However, whether inhibition of COX-2 also plays a dominant role in this drugÂ’s anticancer effects is unclear. For example, a recent study with malignant tumor cells showed that celecoxib could inhibit the growth of these cells in vitro, but COX-2 played no role in this outcome; even more strikingly, the anticancer effects of celecoxib were also obtained with the use of cancer cell types that donÂ’t even contain COX-2. Additional support for the idea that other targets besides COX-2 are important for celecoxib's anticancer effects has come from studies with chemically modified versions of celecoxib. Several dozen analogs of celecoxib were generated with small alterations in their chemical structures. Some of these analogs retained COX-2 inhibitory activity, whereas many others didn't. However, when the ability of all these compounds to kill tumor cells in cell culture was investigated, it turned out that the antitumor potency did not at all depend on whether or not the respective compound could inhibit COX-2, showing that inhibition of COX-2 was not required for the anticancer effects.  One of these compounds, 2,5-dimethyl-celecoxib, which entirely lacks the ability to inhibit COX-2, actually turned out to display stronger anticancer activity than celecoxib itself.
 
Current developer:    Pfizer
 
 


References

1: Derry S, Moore RA. Single dose oral celecoxib for acute postoperative pain in adults. Cochrane Database Syst Rev. 2012 Mar 14;3:CD004233. Review. PubMed PMID: 22419293.

2: Winfield LL, Payton-Stewart F. Celecoxib and Bcl-2: emerging possibilities for anticancer drug design. Future Med Chem. 2012 Mar;4(3):361-83. Review. PubMed PMID: 22393942; PubMed Central PMCID: PMC3398981.

3: McCormack PL. Celecoxib: a review of its use for symptomatic relief in the treatment of osteoarthritis, rheumatoid arthritis and ankylosing spondylitis. Drugs. 2011 Dec 24;71(18):2457-89. doi: 10.2165/11208240-000000000-00000. Review. PubMed PMID: 22141388.

4: Arakawa Y, Nakai N, Katoh N. Celecoxib-induced erythema multiforme-type drug eruption with a positive patch test. J Dermatol. 2011 Dec;38(12):1185-8. doi: 10.1111/j.1346-8138.2010.01182.x. Epub 2011 Mar 21. Review. PubMed PMID: 22103805.

5: Mallen SR, Essex MN, Zhang R. Gastrointestinal tolerability of NSAIDs in elderly patients: a pooled analysis of 21 randomized clinical trials with celecoxib and nonselective NSAIDs. Curr Med Res Opin. 2011 Jul;27(7):1359-66. Epub 2011 May 12. Review. PubMed PMID: 21561397.

6: Sakamoto C, Soen S. Efficacy and safety of the selective cyclooxygenase-2 inhibitor celecoxib in the treatment of rheumatoid arthritis and osteoarthritis in Japan. Digestion. 2011;83(1-2):108-23. Epub 2010 Nov 1. Review. PubMed PMID: 21042022.

7: Amrite A, Pugazhenthi V, Cheruvu N, Kompella U. Delivery of celecoxib for treating diseases of the eye: influence of pigment and diabetes. Expert Opin Drug Deliv. 2010 May;7(5):631-45. Review. PubMed PMID: 20205602; PubMed Central PMCID: PMC2858240.

8: Dubois RN. New, long-term insights from the Adenoma Prevention with Celecoxib Trial on a promising but troubled class of drugs. Cancer Prev Res (Phila). 2009 Apr;2(4):285-7. Epub 2009 Mar 31. Review. PubMed PMID: 19336723.

9: Fakih MG, Rustum YM. Does celecoxib have a role in the treatment of patients with colorectal cancer? Clin Colorectal Cancer. 2009 Jan;8(1):11-4. Review. PubMed PMID: 19203891.

10: O'Connor JP, Lysz T. Celecoxib, NSAIDs and the skeleton. Drugs Today (Barc). 2008 Sep;44(9):693-709. Review. PubMed PMID: 19137124.