Flurbiprofen
[CAS# 5104-49-4]

Identification

• Classification: API >> Antipyretic analgesics >> Non-steroidal anti-inflammatory drugs
• Name: Flurbiprofen
• Synonyms: 3-Fluoro-4-phenylhydratropic acid; Ansaid
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.26
• CAS Registry Number: 5104-49-4
• EC Number: 225-827-6
• SMILES: CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O

Properties

• Solubility: 100 mM (DMSO), 100 mM (ethanol) (Expl)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 110-113 °C (Expl.)
• Index of Refraction: 1.568, Calc.^*
• Boiling Point: 376.2±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 181.3±24.6 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H315-H319-H335-H361
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	2	H361
Germ cell mutagenicity	Muta.	2	H341
Reproductive toxicity	Repr.	2	H361fd
Eye irritation	Eye Irrit.	2A	H319
Reproductive toxicity	Repr.	1B	H360

Discovery and Applications

Flurbiprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is widely used for its analgesic, anti-inflammatory, and antipyretic properties. It is primarily used to manage pain, inflammation, and fever associated with conditions such as arthritis, musculoskeletal disorders, and postoperative recovery. Flurbiprofen was first synthesized in the 1970s as part of the ongoing development of NSAIDs aimed at providing effective pain relief while minimizing the side effects associated with older analgesics like aspirin.

The discovery of flurbiprofen was driven by the need for a drug that could target inflammation effectively while offering a favorable side effect profile. The compound belongs to the propionic acid class of NSAIDs, which includes other well-known drugs like ibuprofen and naproxen. Flurbiprofen works by inhibiting the enzyme cyclooxygenase (COX), which plays a key role in the production of prostaglandins. Prostaglandins are lipid compounds that contribute to inflammation, pain, and fever. By blocking COX, flurbiprofen reduces the production of these compounds, thereby alleviating symptoms such as pain and swelling.

Flurbiprofen was introduced to the market in the 1980s, and its use quickly expanded due to its effectiveness in treating a wide range of inflammatory conditions. One of the key benefits of flurbiprofen is its ability to provide significant pain relief without the extensive gastrointestinal side effects commonly associated with older NSAIDs. Unlike some other NSAIDs, flurbiprofen is less likely to cause stomach irritation and ulcers, making it a preferred choice for many patients with chronic pain conditions.

The primary application of flurbiprofen is in the treatment of acute and chronic pain, particularly in conditions such as osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis. It is also used to treat pain following surgery, including dental procedures and other minor surgical interventions. In addition to its pain-relieving properties, flurbiprofen has been found to be effective in reducing inflammation, which is a key factor in the management of various inflammatory diseases.

Flurbiprofen is also used in the management of fever, as its antipyretic properties help reduce elevated body temperature associated with infections or other inflammatory conditions. Its use in fever management, however, is less common than its application for pain and inflammation. When administered orally, flurbiprofen is rapidly absorbed and metabolized, with its peak plasma concentration typically reached within one to two hours. It is available in various forms, including tablets, oral suspensions, and topical formulations.

In addition to its use in traditional medical applications, flurbiprofen has been studied for its potential in treating other conditions. For example, it has been investigated for use in preventing postoperative inflammation and pain following eye surgeries. Flurbiprofen ophthalmic solutions are used to reduce inflammation and prevent pain after cataract surgery, further expanding its clinical use. Moreover, flurbiprofen’s effectiveness in reducing inflammation and pain has prompted research into its potential role in treating conditions beyond the musculoskeletal system, such as certain types of cancer and cardiovascular diseases.

While flurbiprofen is generally well-tolerated, it is not without risks. Like other NSAIDs, it may cause gastrointestinal side effects such as nausea, vomiting, and in more severe cases, ulcers or bleeding. Long-term use of flurbiprofen can also lead to renal and cardiovascular issues, such as kidney damage and an increased risk of heart attack or stroke. As with other NSAIDs, its use should be carefully monitored, especially in patients with preexisting conditions such as hypertension, heart disease, or gastrointestinal disorders.

In conclusion, flurbiprofen is a widely used NSAID that offers significant benefits in the management of pain, inflammation, and fever. Its discovery and development marked an important step in the evolution of NSAIDs, providing an effective treatment option with a relatively mild side effect profile. Despite its advantages, careful monitoring is required to minimize the risks associated with long-term use, and ongoing research may uncover additional therapeutic applications for this versatile compound.

References

2003. Differences in flurbiprofen pharmacokinetics between CYP2C9*1/*1, *1/*2, and *1/*3 genotypes. European Journal of Clinical Pharmacology, 58(12).
DOI: 10.1007/s00228-003-0574-6

2000. Effect of l-Menthol-Ethanol-Water System on the Systemic Absorption of Flurbiprofen after Repeated Topical Applications in Rabbits. Biological and Pharmaceutical Bulletin, 23(10).
DOI: 10.1248/bpb.23.1254

1994. High-performance liquid chromatographic assay for antiinflammatory agents diclofenac and flurbiprofen in ocular fluids. Journal of Chromatography B: Biomedical Sciences and Applications, 653(2).
DOI: 10.1016/0378-4347(93)e0448-y