Celecoxib
[CAS# 169590-42-5]

Identification

• Classification: API >> Antipyretic analgesics >> Non-steroidal anti-inflammatory drugs
• Name: Celecoxib
• Synonyms: 4-[5-(4-Methylphenyl)-3-trifluoromethyl)-1H-pyrazol-yl]benzenesulfonamide
• Molecular Formula: C₁₇H₁₄F₃N₃O₂S
• Molecular Weight: 381.37
• CAS Registry Number: 169590-42-5 (184007-95-2)
• EC Number: 685-962-5
• SMILES: CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F

Properties

• Solubility: 50 mM (DMSO)
• Melting point: 157-159 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H317-H319-H360
• Safety Statements: P203-P261-P264+P265-P272-P280-P302+P352-P305+P351+P338-P318-P321-P333+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	1B	H360D
Reproductive toxicity	Repr.	1A	H360
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovery and Applications

Celecoxib, with the chemical formula C₁₈H₁₅Cl₂N₁₀, is a widely recognized nonsteroidal anti-inflammatory drug (NSAID) that specifically inhibits cyclooxygenase-2 (COX-2). Discovered in the 1990s, celecoxib has become a critical component in the treatment of various inflammatory conditions and pain.

The discovery of celecoxib was a result of extensive research aimed at developing NSAIDs with fewer gastrointestinal side effects compared to traditional drugs. Researchers identified that inhibiting the COX-2 enzyme, which is involved in the inflammatory process, could provide significant therapeutic benefits while minimizing the adverse effects associated with COX-1 inhibition, which is more commonly linked to gastrointestinal complications.

Celecoxib's synthesis involves a series of chemical reactions that lead to the formation of its distinctive structure, which includes a sulfonamide group and a bicyclic structure derived from the coumarin family. This design was intended to enhance the drug's selectivity for COX-2, thereby improving its safety profile.

In terms of application, celecoxib is primarily used to manage pain and inflammation in conditions such as osteoarthritis, rheumatoid arthritis, and acute pain. Its selective inhibition of COX-2 helps to alleviate symptoms of these conditions without the high risk of gastrointestinal bleeding and ulcers that are common with non-selective NSAIDs.

Celecoxib is also utilized in the management of menstrual pain and certain types of cancer pain, as well as in the treatment of familial adenomatous polyposis (FAP), a genetic condition that increases the risk of colorectal cancer. The drug's efficacy in reducing the number and size of polyps in FAP patients has been a notable application in cancer prevention strategies.

The compound is available in various formulations, including capsules and oral tablets, making it convenient for long-term use. Its pharmacokinetics are favorable, with a high oral bioavailability and a relatively long half-life, which allows for dosing schedules that are convenient for patients.

Overall, celecoxib represents a significant advancement in the field of anti-inflammatory medications, providing effective relief from pain and inflammation while offering a more targeted approach to minimizing gastrointestinal side effects. Its discovery and development underscore the importance of selective drug design in improving therapeutic outcomes and patient safety.

References

2000. Topical application of a selective cyclooxygenase inhibitor suppresses UVB mediated cutaneous inflammation. Prostaglandins & Other Lipid Mediators, 62(4).
DOI: 10.1016/s0090-6980(00)00089-7

2003. Comparison of the efficacy and tolerability of dexibuprofen and celecoxib in the treatment of osteoarthritis of the hip. International Journal of Clinical Pharmacology and Therapeutics, 41(4).
DOI: 10.5414/cpp41153

2003. Studies on the applicability of tamarind kernel powder as a carrier in the dissolution enhancement of poorly water soluble drug, celecoxib. Bollettino Chimico Farmaceutico, 142(2).
PMID: 12705095