Ibuprofen
| (R/S)-ibuprofen | |
| (R)-ibuprofen | |
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| Pronunciation | /ˈaɪbjuːproʊfɛn/ ⓘ, /aɪbjuːˈproʊfən/, EYE-bew-PROH-fən | 
| Trade names | Brufen, others | 
| Other names | isobutylphenylpropionic acid | 
| AHFS/Drugs.com | Monograph | 
| MedlinePlus | a682159 | 
| License data | |
| Pregnancy category | 
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| Routes of administration | By mouth, rectal, topical, intravenous | 
| Drug class | Nonsteroidal anti-inflammatory drug (NSAID) | 
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| Legal status | |
| Legal status | 
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| Pharmacokinetic data | |
| Bioavailability | 80–100% (oral), 87% (rectal) | 
| Protein binding | 98% | 
| Metabolism | Liver (CYP2C9) | 
| Metabolites | ibuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen | 
| Onset of action | 30 min | 
| Elimination half-life | 2–4 h | 
| Excretion | Urine (95%) | 
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.036.152 | 
| Chemical and physical data | |
| Formula | C13H18O2 | 
| Molar mass | 206.285 g·mol−1 | 
| 3D model (JSmol) | |
| Chirality | Racemic mixture | 
| Density | 1.03 g/cm3 | 
| Melting point | 75 to 78 °C (167 to 172 °F) | 
| Boiling point | 157 °C (315 °F) at 4 mmHg | 
| Solubility in water | 0.021 | 
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Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It can be taken orally (by mouth) or intravenously. It typically begins working within an hour.
Common side effects include heartburn, nausea, indigestion, and abdominal pain. Potential side effects include gastrointestinal bleeding. Long-term use has been associated with kidney failure, and rarely liver failure, and it can exacerbate the condition of people with heart failure. At low doses, it does not appear to increase the risk of myocardial infarction (heart attack); however, at higher doses it may. Ibuprofen can also worsen asthma. While its safety in early pregnancy is unclear, it appears to be harmful in later pregnancy, so it is not recommended during that period. It works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX). Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.
Ibuprofen was discovered in 1961 by Stewart Adams and John Nicholson while working at Boots UK Limited and initially sold as Brufen. It is available under a number of brand names including Advil, Brufen, Motrin, and Nurofen. Ibuprofen was first sold in 1969 in the United Kingdom and in 1974 in the United States. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 33rd most commonly prescribed medication in the United States, with more than 17 million prescriptions.