- Molecular NameAminosalicylic Acid
- Synonym4-aminosalicylic acid; 4-ASA; Amino-PAS; Aminosalicylate Sodium; APAS; P-Aminosalicylic Acid; Para-Amino Salicylic Acid; Para-aminosalicylic acid; PAS; PASK
- Weight153.137
- Drugbank_IDDB00233
- ACS_NO65-49-6
- Show 3D model
- LogP (experiment)0.87
- LogP (predicted, AB/LogP v2.0)1.4
- pkapKa1.8 (-NH2), 3.6 (-COOH)
- LogD (pH=7, predicted)-2.08
- Solubility (experiment)1.69 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)0.81
- LogSw (predicted, AB/LogsW2.0)2.24
- Sw (mg/ml) (predicted, ACD/Labs)0.51
- No.of HBond Donors4
- No.of HBond Acceptors4
- No.of Rotatable Bonds1
- TPSA83.55
- StatusFDA approved
- AdministrationN/A
- PharmacologyAn antibiotic used to treat tuberculosis. This organic compound has been use since the 1940s for the treatment of inflammatory bowel diseases (IBDs), where it has shown greater potency in Ulcerative Colitis and Crohn's disease. It is thought to act via NF-κB (nuclear factor-kappa B) inhibition and free radical scavenging. 5-Aminosalicylic acid, sold under the name mesalazine, is a closely related compound that also has medical uses.
- Absorption_valueN/A
- Absorption (description)Aminosalicylic acid is readily absorbed after oral administration and widely distributed throughout the body, with high concentrations in the kidneys, lungs and liver.
- Caco_2N/A
- BioavailabilityN/A
- Protein binding55.0
- Volume of distribution (VD)N/A
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmHepatic. It is metabolised by acetylation to p-acetamidosalicylic acid and by conjugation with glycine, producing p-aminosalicyluric acid; both metabolites are inactive.
- Half life0.5~1 h (aminosalicylic acid); 1.5 h (p-acetamidosalicylic acid)
- ExcretionMore than 80% of a dose is excreted in the urine in 24 h with about 50% of the dose consisting of p-acetamidosalicylic acid; up to 25% of the dose may be excreted as free and acetylated p-aminosalicyluric acid, and the remainder is mostly unchanged drug with small amounts of 2,4-dihydroxybenzoic acid.
- Urinary ExcretionN/A
- CleranceN/A
- ToxicityAnimal toxicity. LD50=4 gm/kg (orally in mice); LD50=3650 mg/kg (orally in rabbits). Adverse effects. The most common side effect is gastrointestinal intolerance manifested by nausea, vomiting, diarrhea, and abdominal pain. Hypersensitivity reactions: Fever, skin eruptions of various types, including exfoliative dermatitis, infectious mononucleosis-like, or lymphoma-like syndrome, leucopenia, agranulocytosis, thrombocytopenia, Coombs' positive hemolytic anemia, jaundice, hepatitis, pericarditis, hypoglycemia, optic neuritis, encephalopathy, Leoffler's syndrome, and vasculitis and a reduction in prothrombin. Crystalluria may be prevented by the maintenance of urine at a neutral or an alkaline pH.
- LD50 (rat)N/A
- LD50 (mouse)N/A