ibuprofen

Also known as U-18573, 4-isobutylhydratropic acid, (RS)-ibuprofen, (4-isobutylphenyl)-alpha-methylacetic acid, (+-)-p-isobutylhydratropic acid, (+-)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid, (+-)-2-(p-isobutylphenyl)propionic acid, 2-(4-isobutylphenyl)propanoic acid

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.

AI overview

Ibuprofen is a common medication that reduces pain, fever, and inflammation in conditions ranging from menstrual cramps to migraines and arthritis. It can be taken by mouth or injected into the bloodstream, and usually starts working within an hour.

AI-generated from the Wikipedia summary — may contain errors.

Key facts

Drug.pronounce: , ,
Drug.Watchedfields: changed
Drug.verifiedrevid: 464191340
Drug.image: Ibuprofen.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.caption: (R/S)-ibuprofen
Drug.image2: Ibuprofen-3D-balls.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.caption2: (R)-ibuprofen
Drug.alt2: (R)-ibuprofen
Drug.chirality: Racemic mixture
Drug.tradename: Brufen, others
Drug.MedlinePlus: a682159
Drug.DailyMedID: Ibuprofen
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth, rectal, topical, intravenous

via Wikipedia infobox

Chemical data

Formula: C13H18O2
Molecular weight: 206.28 g/mol
IUPAC name: 2-[4-(2-methylpropyl)phenyl]propanoic acid
SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
InChIKey: HEFNNWSXXWATRW-UHFFFAOYSA-N
XLogP: 3.5
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

19,886 papers

Ibuprofen.ReviewAnnals of internal medicine · 1979Kantor TGDOI: 10.7326/0003-4819-91-6-877
Ibuprofen: Toxicology and Biodegradation of an Emerging Contaminant.ReviewMolecules (Basel, Switzerland) · 2023Jan-Roblero J, Cruz-Maya JADOI: 10.3390/molecules28052097
Clinical pharmacokinetics of ibuprofen. The first 30 years.ReviewClinical pharmacokinetics · 1998Davies NMDOI: 10.2165/00003088-199834020-00002
Ibuprofen and Other Arylpropionics: The Relevance in Immediate Hypersensitivity Drug Reactions.ReviewInternational archives of allergy and immunology · 2024Blanca-Lopez N, Agundez JAG, Fernández J et al.DOI: 10.1159/000539043
Ibuprofen: a monograph.ReviewAmerican pharmacy · 1991Aycock DG
Ibuprofen: a journey from prescription to over-the-counter use.ReviewJournal of the Royal Society of Medicine · 2007Moore NDOI: 10.1177/014107680710004801s01
Ibuprofen: from invention to an OTC therapeutic mainstay.ReviewInternational journal of clinical practice. Supplement · 2013Rainsford KDDOI: 10.1111/ijcp.12055
Use of ibuprofen for the closure of patent ductus arteriosus in preterm infants: a systematic review of meta-analyses.Journal of comparative effectiveness research · 2021Al-Shaibi S, Abushanab D, Alhersh E et al.DOI: 10.2217/cer-2020-0235

via PubMed

Described at

Ibuprofen, (+-)- | C13H18O2 | CID 3672 - PubChem

Ibuprofen, (+-)- | C13H18O2 | CID 3672 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

pubchem.ncbi.nlm.nih.gov →

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Wikidata facts

Mass: 206.131
Image: Ibuprofen.svg

Show 8 more facts

Commons category: Ibuprofen
chemical formula: C₁₃H₁₈O₂
World Health Organisation international non-proprietary name: ibuprofenum
MCN code: 2916.39.20
canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
defined daily dose: 30
melting point: 77
described at URL: www.stylist.co.uk/fitness-health/wellbeing/ibuprofen-paracetamol-gp-pharmacist/999946

Sources (13)

via Wikidata · CC0

~20 min read

Article

21 sections

Contents

Medical uses
Ibuprofen lysine
Adverse effects
Cardiovascular risk
Skin
Pregnancy
Interactions
Alcohol
Aspirin
Paracetamol (acetaminophen)
Overdose
Pharmacology
Pharmacokinetics
Metabolism
Chemistry
Stereochemistry
History
Availability and administration
Research
References
External links

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.