Table of Contents
Introduction
Generic Name: Dexibuprofen
Chemical Formula: C13H18O2
Drug Class: Nonsteroidal Anti-inflammatory Drug (NSAID)
Stereochemistry: (S)-Ibuprofen, the active form of ibuprofen
Dexibuprofen is the active form (S-enantiomer) of the racemic mixture found in ibuprofen. This enantiomer is responsible for the drug’s pain-relieving and anti-inflammatory effects. It’s known for its efficacy at lower doses compared to regular ibuprofen, which allows for reduced gastrointestinal side effects while maintaining the same degree of therapeutic effect.
Chemical Structure and Isomerism
Dexibuprofen is a stereoisomer, specifically it is the S(+)-enantiomer of ibuprofen, which is slightly more responsible for its therapeutic benefits. Unlike the racemic mixture (containing both R and S enantiomers), the S-enantiomer is more efficient at reducing pain and inflammation. Removing the inactive R-enantiomer means lower doses are required, which in theory, reduces the risk of side effects, particularly gastrointestinal issues.
Mechanism of Action
Dexibuprofen works by inhibiting cyclooxygenase (COX) enzymes, specifically COX-2. These enzymes play a critical role in converting arachidonic acid into prostaglandins, which are responsible for causing inflammation and pain.
- COX-2 Inhibition: By inhibiting the COX-2 enzyme, dexibuprofen reduces the production of inflammatory prostaglandins, which are key players in the body’s inflammation process.
- COX-1 Inhibition: Although dexibuprofen also inhibits COX-1, which is responsible for protecting the stomach lining, its selectivity for COX-2 is thought to be slightly higher than racemic form ibuprofen. Hence it causes a less stomach discomfort/upset.
Pharmacokinetics
- Absorption:
After oral administration, dexibuprofen is quickly absorbed by the gastrointestinal tract. The drug reaches peak plasma concentrations in about 1 to 2 hours. - Distribution:
It has a high plasma protein-binding rate of around 99%, ensuring it stays in circulation for effective targeting of inflamed tissues. - Metabolism:
The liver metabolizes the drug into inactive compounds, primarily via the cytochrome P450 enzyme pathway. The main metabolic processes are hydroxylation and glucuronidation. - Excretion:
The active drug and its metabolites are mainly excreted via the kidneys. Approximtely 60-90% is eliminated through urine, with a half-life of about 2-3 hours.
Clinical Uses
- Musculoskeletal Disorders: Used to treat chronic conditions like osteoarthritis, rheumatoid arthritis, and other inflammatory joint diseases. For people with rheumatoid arthritis, dexibuprofen alleviates pain and inflammation in the joints, preventing further joint damage and improving daily function. It is also often used to treat osteoarthritis, helping to reduce joint pain, stiffness, and inflammation, improving mobility and quality of life.
- Acute Pain Relief: Effective for treating pain from injuries, surgeries, and dental procedures.
- Menstrual Pain: Dexibuprofen may be prescribed for women experiencing painful menstrual cramps (dysmenorrhea).
- Fever Management: Used as an antipyretic for reducing fevers caused by infections or inflammatory conditions. Dexibuprofen’s acts on the hypothalamus makes it effective for lowering fever by reducing the body’s production of prostaglandins, which are responsible for an increase in body temperature
Dosage and Administration
- For Pain and Inflammation:
- Adults: The usual dosage is 400-800 mg per day, divided into 2 or 3 doses. The maximum daily dose should not exceed 1200 mg.
- For Fever:
- Adults: 200-400 mg every 6 to 8 hours is used to manage fever, with a maximum daily dose of 1200 mg.
Always take dexibuprofen with food to reduce the risk of gastrointestinal discomfort.
Side Effects of Dexibuprofen
- Common Side Effects:
- Nausea or upset stomach.
- Diarrhea or constipation.
- Headache or dizziness.
- Serious Side Effects:
- Gastrointestinal Ulcers: Prolonged use can increase the risk of stomach ulcers or bleeding.
- Renal Impairment: Long-term use may cause damage to the kidneys, especially in individuals with existing kidney conditions.
- Cardiovascular Risk: Prolonged use may increase the risk of heart attack or stroke.
Contraindications of Dexibuprofen
- Allergies to NSAIDs: Dexibuprofen should be avoid in individuals allergic to ibuprofen or other NSAIDs.
- Peptic Ulcer Disease: Patients with active or a history of gastrointestinal ulcers should not use dexibuprofen due to the risk of exacerbating these conditions.
- Severe Liver or Kidney Disease: Avoid in patients with severe hepatic or renal impairment due to the risk of further deterioration in organ function.
- Pregnancy : It should not be used during the third trimester of pregnancy, as it may cause complications.
Drug Interactions
- Anticoagulants (e.g., Warfarin): Increases the risk of bleeding when used with blood thinners.
- Other NSAIDs: Combining dexibuprofen with other NSAIDs increases the risk of gastrointestinal side effects and kidney issues.
- Diuretics and ACE Inhibitors: May reduce the effectiveness of these drugs and increase the risk of kidney damage.
Warnings and Precautions
- Gastrointestinal Health: Use with caution in individuals with a history of gastrointestinal problems, as this drug can cause ulcers or bleeding.
- Kidney Monitoring: Regular kidney function tests are recommended for individuals taking dexibuprofen long-term, especially those with pre-existing kidney conditions.
- Cardiovascular Health: Monitor cardiovascular health, especially in patients at risk of heart attack or stroke, as long-term NSAID use may increase these risks.