5-Aminosalicylic acid CAS No. 89-57-6

Product Description

5-Aminosalicylic acid (5-ASA), also known as mesalazine or mesalamine, is a widely used anti-inflammatory drug primarily indicated for the treatment of inflammatory bowel diseases (IBD), such as ulcerative colitis and Crohn's disease. It is available in various forms, including oral tablets and capsules (e.g., Asacol, Pentasa, Lialda) and rectal formulations like suppositories, enemas, and foams (e.g., Canasa). The drug works locally in the intestines to reduce inflammation by inhibiting the synthesis of prostaglandins and leukotrienes, scavenging free radicals, and modulating inflammatory pathways. It is effective for inducing and maintaining remission in mild to moderate ulcerative colitis and is sometimes used off-label for Crohn's disease, particularly in cases involving the colon. Common side effects include headache, nausea, abdominal pain, and diarrhea, while more serious but rare adverse effects may involve kidney dysfunction, pancreatitis, and blood disorders. Regular renal monitoring is recommended, and the drug should be avoided in patients with salicylate allergies. It is generally considered safe during pregnancy and lactation (Category B).

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Product Use & Characteristics

Properties of 5-Aminosalicylic Acid (5-ASA)

• Chemical Name: 5-Aminosalicylic acid

• IUPAC Name: 5-amino-2-hydroxybenzoic acid

• Molecular Formula: C₇H₇NO₃

• Molecular Weight: 153.14 g/mol

• CAS Number: 89-57-6

• Structure: A derivative of salicylic acid with an amino group (-NH₂) in the 5-position, a hydroxyl group (-OH) in the 2-position, and a carboxylic acid group (-COOH) in the 1-position.

• Chemical Structure:

  • Benzene Ring: The core structure is a six-carbon aromatic ring.

  • Amino Group (NH₂): Attached to the benzene ring at the 5th carbon position.

  • Hydroxyl Group (OH): Attached to the benzene ring at the 2nd carbon position.

  • Carboxylic Acid Group (COOH): Attached to the benzene ring at the 1st carbon position.

Uses of 5-Aminosalicylic Acid (5-ASA)

• Primary Indications:

  • Ulcerative Colitis: First-line treatment for inducing and maintaining remission in mild to moderate cases.

  • Crohn's Disease: Used off-label for mild inflammation and symptoms, particularly in colonic involvement.

  • Diverticulitis: Recent guidance suggests its use for acute uncomplicated diverticulitis.

  • Irritable Bowel Syndrome with Diarrhea (IBS-D): Some studies suggest it may offer modest effectiveness in alleviating symptoms.

Forms of Administration

• Oral Forms:

  • Tablets/Capsules: pH- or time-release formulations to target the intestines (e.g., Asacol, Pentasa, Lialda).

• Rectal Forms:

  • Suppositories, Enemas, Foams: For localized treatment of distal colitis (e.g., Canasa).

Mechanism of Action

• Inflammatory Pathway Modulation: Decreases the synthesis of prostaglandins and leukotrienes by modulating the cyclooxygenase (COX) and lipooxygenase pathways.

• Free Radical Scavenging: Acts as a free radical scavenger and antioxidant, protecting the mucosal lining from damage.

• Inhibition of NF-κB: Reduces the expression of inflammatory cytokines by inhibiting nuclear factor-kappa B (NF-κB).

• Activation of PPAR-γ: Activates peroxisome proliferator-activated receptor-gamma (PPAR-γ), which has anti-inflammatory effects in the gut.

Side Effects

• Common Side Effects:

  • Headache

  • Nausea, vomiting, abdominal pain, and cramping

  • Diarrhea

  • Rash or fever

  • Loss of appetite

  • Gas

• Serious but Rare Side Effects:

  • Kidney problems (e.g., decreased kidney function, kidney stones)

  • Liver problems (e.g., jaundice, dark urine, pale stools)

  • Acute intolerance syndrome (symptoms similar to worsening IBD)

  • Blood disorders (e.g., low white blood cell counts)

  • Allergic or hypersensitivity reactions

  • Pancreatitis or pericarditis

Precautions and Monitoring

• Renal Monitoring: Regular blood tests to monitor kidney function due to the risk of interstitial nephritis.

• Salicylate Allergy: Avoid in patients with salicylate allergies due to possible cross-reactivity.

• Pregnancy/Lactation: Generally considered safe (Category B).

Drug Interactions

• NSAIDs: May increase gastrointestinal irritation.

• Azathioprine/6-MP: Increased risk of myelosuppression.

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