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4-Aminosalicylic acid

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4-Aminosalicylic acid Basic information
4-Aminosalicylic acid Chemical Properties
  • Melting point:135-145 °C (lit.)
  • Boiling point:276.03°C (rough estimate)
  • Density 1.3585 (rough estimate)
  • refractive index 1.5500 (estimate)
  • storage temp. Keep in dark place,Inert atmosphere,Room temperature
  • solubility 1.69g/l
  • form Powder
  • pka3.25(at 25℃)
  • color Colorless
  • PH3.5 (1g/l, H2O, 20℃)
  • Water Solubility 2 g/L (20 ºC)
  • Merck 14,477
  • BRN 473071
  • CAS DataBase Reference65-49-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceAminosalicylic acid(65-49-6)
  • EPA Substance Registry System4-Aminosalicylic acid (65-49-6)
Safety Information
  • Language:EnglishProvider:PAS
  • Language:EnglishProvider:SigmaAldrich
  • Language:EnglishProvider:ACROS
  • Language:EnglishProvider:ALFA
4-Aminosalicylic acid Usage And Synthesis
  • Chemical Propertiesbeige powder
  • OriginatorPamisyl,Parke Davis,US,1948
  • Usesantimycobacterial antitubercular;NF-kB inhibitor
  • UsesAn antibiotic used to treat tuberculosis.
  • DefinitionChEBI: An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.
  • Indicationsp-Aminosalicylic acid is a bacteriostatic that inhibits most tuberculous mycobacteria. In terms of tuberculostatic activity it is inferior to isoniazid and streptomycin. It is nephroand hepatotoxic, and is rarely used. A synonym of this drug is apacizin.
  • Manufacturing ProcessAs described in US Patent 427,564, aminosalicylic acid may be prepared from m-aminophenol by heating with ammonium carbonate in solution under pressure.
    Alternatively, aminosalicylic acid may be made from sodium p-aminosalicylate as described in US Patent 2,844,625 as follows: 196 grams of commercial sodium para-aminosalicylate (18.5% H2O) was dissolved in 196 ml of water and 150 ml of isopropanol. 6 grams of sodium bisulfite was dissolved in the solution and the solution filtered. While stirring and keeping the temperature between 25-31°C, seven grams of 85% formic acid and 27.5 grams of 95% sulfuric acid in 150 ml of water was added during 1 ? hours. The mixture was stripped 1 hour longer, cooled to 23°C and filtered. The filter cake was washed with 100 cubic centimeters of water, further washed with 100 cc of 25% isopropanol and 100 cc of water, and vacuum dried to constant weight at 45- 50°C. Weight of p-aminosalicylic acid was 76.5 grams (92.7% yield) exhibiting a bulk density of 47 cc/oz.
  • brand nameParasal (Panray); Paser (Jacobus).
  • Therapeutic FunctionAntitubercular
  • General Description4-Aminosalicylic acid occurs as a white to yellowish white crystalline solid that darkens on exposure to light or air. It is slightly soluble in water but more soluble in alcohol. Alkali metal salts and the nitric acid salt are soluble in water, but the salts of hydrochloric acid and sulfuric acid are not. The acid undergoes decarboxylation when heated. An aqueous solution has a pH of approximately 3.2. PAS is administered orally in the form of the sodium salt, usually in tablet or capsule form. Symptoms of gastrointestinal irritation are common with both the acid and the sodium salt. Various enteric-coated dosage forms have been used in an attempt to overcome this disadvantage. Other forms that are claimed to improve gastrointestinal tolerance include the calcium salt, the phenyl ester, and a combination with an anion exchange resin (Rezi-PAS). An antacid such as aluminum hydroxide is frequently prescribed. The oral absorption of PAS is rapid and nearly complete, and it is widely distributed into most of the body fluids and tissues, with the exception of the CSF, in which levels are significantly lower.It is excreted primarily in the urine as both unchanged drug and metabolites.
  • Mechanism of actionp-aminosalicylic acid is thought to act as an antimetabolite interfering with the incorporation of p-aminobenzoic acid into folic acid. When coadministered with INH, PAS is found to reduce the acetylation of INH, itself being the substrate for acetylation, thus increasing the plasma levels of INH. This action may be especially valuable in patients who are rapid acetylators.
  • Safety ProfileModerately toxic ingestion andother routes. An eye irritant. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.
  • Chemical Synthesisp-Aminosalicylic acid, 5-amino-2-hydroxybenzoic acid (34.1.22), is synthesized in a Kolbe reaction, which consists of direct interaction of m-aminophenol with potassium bicarbonate and carbon dioxide while heating at a moderate pressure of 5–10 atm.

  • Metabolismp-aminosalicylic acid is extensively metabolized by acetylation of the amino group and by conjugation with glucuronic acid and glycine at the carboxyl group. It is used primarily in cases of resistance, retreatment, and intolerance of other agents and is available from the CDC.
  • Purification MethodsCrystallise the acid from EtOH. [Beilstein 14 IV 1967.]
4-Aminosalicylic acid Preparation Products And Raw materials
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