4-Aminosalicylic acid
- CAS No.
- 65-49-6
- Chemical Name:
- 4-Aminosalicylic acid
- Synonyms
- 4-AMINO-2-HYDROXYBENZOIC ACID;PAS;AMINOSALICYLIC ACID;Pasa;4-Asa;P-AMINOSALICYLIC ACID;Apas;Paser;Aminox;Parasal
- CBNumber:
- CB9679687
- Molecular Formula:
- C7H7NO3
- Molecular Weight:
- 153.14
- MOL File:
- 65-49-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/15 19:00:21
| 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 |
| pka | 3.25(at 25℃) |
| color | Colorless |
| PH | 3.5 (1g/l, H2O, 20℃) |
| Water Solubility | 2 g/L (20 ºC) |
| Merck | 14,477 |
| BRN | 473071 |
| BCS Class | 4/2 |
| Stability | Hygroscopic |
| CAS DataBase Reference | 65-49-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Aminosalicylic acid(65-49-6) |
| EPA Substance Registry System | 4-Aminosalicylic acid (65-49-6) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H319-H335-H315 | |||||||||
| Precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P405-P501a-P305+P351+P338 | |||||||||
| Hazard Codes | Xn,Xi,T | |||||||||
| Risk Statements | 22-36-36/37/38-45-35-61 | |||||||||
| Safety Statements | 26-37/39-45-53-36-36/37/39 | |||||||||
| RIDADR | UN 1789 8/PG 3 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | VO1225000 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29225000 | |||||||||
| Toxicity | LD50 orally in mice: 4 g/kg (Bavin) | |||||||||
| NFPA 704 |
|
4-Aminosalicylic acid price More Price(10)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A79604 | 4-Aminosalicylic acid 99% | 65-49-6 | 5G | ₹2067.58 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1746 | 4-Aminosalicylic acid Pharmaceutical Secondary Standard; Certified Reference Material | 65-49-6 | 500MG | ₹12167.3 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A79604 | 4-Aminosalicylic acid 99% | 65-49-6 | 100G | ₹5325.9 | 2022-06-14 | Buy |
| TCI Chemicals (India) | A0420 | 4-Aminosalicylic Acid | 65-49-6 | 25G | ₹3200 | 2022-05-26 | Buy |
| TCI Chemicals (India) | A0420 | 4-Aminosalicylic Acid | 65-49-6 | 100G | ₹8100 | 2022-05-26 | Buy |
4-Aminosalicylic acid Chemical Properties,Uses,Production
Chemical Properties
beige powder
Uses
antimycobacterial antitubercular;NF-kB inhibitor.
4-Aminosalicylic acid (p-aminosalicylic acid, PAS), an antituberculosis drug, is a model active pharmaceutical ingredient to study salt and cocrystal formation in a multiple hydrogen-bonding functionality molecule with carboxylic acid, amine, and phenol groups.
It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease.It is typically taken by mouth.
Application
4-Aminosalicylic acid (4-ASA) can be used in the synthesis of:
Azo derivatives of 4-ASA with anti-inflammatory effects.
Ammonium 4-aminosalicylate salt polymorphs which are used as pharmaceutical ingredients.
Salicylic acid-triazole analogs which are used as quorum sensing inhibitors against Pseudomonas aeruginosa.
Indications
p-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.
Definition
ChEBI: An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.
General Description
4-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.
Biological Activity
4-Aminosalicylic acid is an antimetabolite of p-aminobenzoic acid (PABA) that has antibacterial activity.It is active against streptomycin-sensitive and -resistant strains of M. tuberculosis (MICs = 0.78 and 0.39 μg/ml, respectively), an effect that can be reversed by PABA. 4-Aminosalicylic acid is an alternative substrate for mycobacterial dihydropteroate synthase (FolP1) and misincorporation into the folate pathway leads to accumulation of several folate-dependent metabolites including serine, homocysteine, dUMP, and AICAR, markers of folate pathway inhibition, in a concentration-dependent manner. It reverses manganese-induced increases in rat hippocampal levels of NOD-like receptor protein 3 (NLRP3), cleaved caspase-1, and phosphorylated p65, markers of NLRP3 inflammasome-dependent pyroptosis, when administered at a dose of 300 mg/kg. 4-Aminosalycilic acid is also a building block that has been used in the synthesis of luminescent lanthanide complexes. Formulations containing 4-aminosalicylic acid have been used in the treatment of tuberculosis.
Mechanism of action
p-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 Profile
Moderately toxic ingestion andother routes. An eye irritant. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.
Metabolism
p-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 Methods
Crystallise the acid from EtOH. [Beilstein 14 IV 1967.]
4-Aminosalicylic acid Preparation Products And Raw materials
Raw materials
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