Dexibuprofen

Dexibuprofen
ATC Code M01AE14
Formula C13H18O2
Molar Mass (g·mol−1) 206,28
Physical State solid
Melting Point (°C) 49–53
CAS Number 51146-56-6
PUB Number 39912
Drugbank ID DB09213
Solubility practically insoluble in water

Basics

Dexibuprofen is the (S)-enantiomer (levorotatory) of the racemic analgesic ibuprofen. Dexibuprofen, unlike ibuprofen, has twice the potency. This means that half the dose of dexibuprofen is equally potent. Dexibuprofen is a drug in the nonsteroidal anti-inflammatory drug (NSAID) class that is used to treat pain, fever, and inflammation. These include painful menstrual bleeding, migraines, and rheumatoid arthritis. It can be administered orally in the form of tablets or capsules, or intravenously. In most preparations, the drug is available without a prescription as an "over-the-counter" product.

Pharmacology

Pharmacokinetics

NSAIDs such as dexibuprofen act by inhibiting cyclooxygenase (COX) enzymes, which convert arachidonic acid to prostaglandins. These act as the mediators of pain, inflammation and fever. It also inhibits the formation of thromboxane A2 (which stimulates platelet aggregation, leading to the formation of blood clots). Dexibuprofen is a non-selective COX inhibitor because it inhibits both isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory effects of NSAIDs appear to act primarily by inhibiting COX-2. Inhibition of COX-1 is instead responsible for the adverse effects on the gastrointestinal tract.

Pharmacokinetics

The pharmacokinetics are very similar to those of ibuprofen. After oral administration, the maximum serum concentration is reached after 2.25-5 hours. Up to 99% of the drug is bound to plasma proteins. Most of the drug is metabolized in the liver and excreted in the urine within 24 hours; 1% of the given dose is excreted in the stool.

Drug interactions

Drinking alcohol while taking Dexibuprofen may increase the risk of stomach bleeding.

Dexibuprofen may possibly interfere with the antiplatelet effect of low-dose aspirin (acetylsalicylic acid), possibly making aspirin less effective when used for cardioprotection and stroke prevention.

Toxicity

Side Effects

Adverse effects include:

  • Nausea
  • Dyspepsia
  • Diarrhea
  • Constipation
  • gastrointestinal ulceration/bleeding
  • headache
  • Dizziness
  • Rash
  • salt and fluid retention
  • Hypertension

Toxicological data

LD50 (rat,oral): 636 mg-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017

Editorial principles

All information used for the content comes from verified sources (recognised institutions, experts, studies by renowned universities). We attach great importance to the qualification of the authors and the scientific background of the information. Thus, we ensure that our research is based on scientific findings.

Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter is a writer on pharmaceutical topics in Medikamio's medical editorial team. He is in the last semester of his pharmacy studies at the University of Vienna and loves scientific work in the field of natural sciences.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer has been a freelance writer for Medikamio since 2020 and studied pharmacy at the University of Vienna. She works as a pharmacist in Vienna and her passion is herbal medicines and their effects.

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