Back Ibuprofeen Afrikaans Ibuprofeno AN إيبوبروفين Arabic Ibuprofeno AST ایبوپروفن AZB Ибупрофен Bulgarian आइबूप्रोफेन Bihari আইবুপ্রোফেন Bengali/Bangla པུ་རོ་ཧྥེན་ Tibetan Ibuprofen BS

Ibuprofen

Ibuprofen
(R)-ibuprofen
Clinical data
Pronunciation/ˈaɪbjuːproʊfɛn/, /aɪbjuːˈproʊfən/, EYE-bew-PROH-fən
Trade namesAdvil, Motrin, Nurofen, others
Other namesisobutylphenylpropionic acid
AHFS/Drugs.comMonograph
MedlinePlusa682159
License data
Pregnancy
category
Routes of
administration		Oral (by mouth), rectal, topical, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80–100% (orally),[3] 87% (rectal)
Protein binding98%[4]
MetabolismLiver (CYP2C9)[4]
Metabolitesibuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen
Onset of action30 min[5]
Elimination half-life2–4 h[6]
ExcretionUrine (95%)[4][7]
Identifiers
  • (RS)-2-(4-(2-Methylpropyl)phenyl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.036.152 Edit this at Wikidata
Chemical and physical data
FormulaC13H18O2
Molar mass206.285 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Density1.03 g/cm3
Melting point75 to 78 °C (167 to 172 °F)
Boiling point157 °C (315 °F) at 4 mmHg
Solubility in water0.021 mg/mL (20 °C)
  • CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O
  • InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) checkY
  • Key:HEFNNWSXXWATRW-UHFFFAOYSA-N checkY
  (verify)

Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation.[8] This includes painful menstrual periods, migraines, and rheumatoid arthritis.[8] It may also be used to close a patent ductus arteriosus in a premature baby.[9][8] It can be used orally (by mouth) or intravenously.[8] It typically begins working within an hour.[8]

Common side effects include heartburn and a rash.[8] Compared to other NSAIDs, it may have other side effects such as gastrointestinal bleeding.[10] It increases the risk of heart failure, kidney failure, and liver failure.[8] At low doses, it does not appear to increase the risk of heart attack; however, at higher doses it may.[10] Ibuprofen can also worsen asthma.[10] While its safety in early pregnancy is unclear,[8] it appears to be harmful in later pregnancy, so it is not recommended during that period.[11] Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX).[8] Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.[10]

Ibuprofen was discovered in 1961 by Stewart Adams and John Nicholson[12] while working at Boots UK Limited and initially marketed as Brufen.[13] It is available under a number of brand names, including Nurofen, Advil, and Motrin.[8][14] Ibuprofen was first marketed in 1969 in the United Kingdom and in 1974 in the United States.[8][13] It is on the World Health Organization's List of Essential Medicines.[15] It is available as a generic medication.[8] In 2021, it was the 36th-most commonly prescribed medication in the United States, with more than 17 million prescriptions.[16][17]

  1. ^ Use During Pregnancy and Breastfeeding
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Davanzo R, Bua J, Paloni G, Facchina G (November 2014). "Breastfeeding and migraine drugs". European Journal of Clinical Pharmacology (Review). 70 (11): 1313–1324. doi:10.1007/s00228-014-1748-0. PMID 25217187. S2CID 17144030.
  4. ^ a b c Davies NM (February 1998). "Clinical pharmacokinetics of ibuprofen. The first 30 years". Clinical Pharmacokinetics. 34 (2): 101–154. doi:10.2165/00003088-199834020-00002. PMID 9515184. S2CID 1186212.
  5. ^ "ibuprofen". Archived from the original on 13 January 2015. Retrieved 31 January 2015.
  6. ^ Grosser T, Ricciotti E, FitzGerald GA (August 2017). "The Cardiovascular Pharmacology of Nonsteroidal Anti-Inflammatory Drugs". Trends in Pharmacological Sciences (Review). 38 (8): 733–748. doi:10.1016/j.tips.2017.05.008. PMC 5676556. PMID 28651847.
  7. ^ "Brufen Tablets And Syrup" (PDF). Therapeutic Goods Administration. 31 July 2012. Archived from the original on 20 August 2016. Retrieved 8 May 2014.
  8. ^ a b c d e f g h i j k l "Ibuprofen". The American Society of Health-System Pharmacists. Archived from the original on 9 September 2017. Retrieved 12 October 2016.
  9. ^ "Pedea EPAR". European Medicines Agency (EMA). 29 July 2004. Retrieved 24 February 2024.
  10. ^ a b c d British National Formulary, March 2014–September 2014 (2014 ed.). London: British Medical Association. 2014. pp. 686–688. ISBN 978-0857110862.
  11. ^ "Ibuprofen Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 9 September 2017. Retrieved 22 May 2016.
  12. ^ Kindy D. "The Inventor of Ibuprofen Tested the Drug on His Own Hangover". Smithsonian Magazine. Retrieved 3 July 2021. Stewart Adams and his associate John Nicholson invented a pharmaceutical drug known as 2-(4-isobutylphenyl) propionic acid.
  13. ^ a b Halford GM, Lordkipanidzé M, Watson SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams". Platelets. 23 (6): 415–422. doi:10.3109/09537104.2011.632032. PMID 22098129. S2CID 26344532.
  14. ^ "Chemistry in your cupboard: Nurofen". RSC Education. Archived from the original on 5 June 2014.
  15. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  16. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  17. ^ "Ibuprofen. Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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