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Sodium 4-Aminosalicylate, the sodium salt of aminosalicylic acid and an analog of PABA/para-aminobenzoic acid, is an antibiotic used to treat MDR-TB/multidrug-resistant tuberculosis via NF-κB inhibition and free radical scavenging. Sodium 4-Aminosalicylate competes with PABA for enzymes necessary for the synthesis of folate in order to exert its bacteriostatic activity against Mycobacterium tuberculosis. It responds quickly to DPPH, indicating a potent anti-radical activity. A chain-breaking type of antioxidant activity is suggested by the 4-aminosalicylate's rapid scavenging of peroxyl radicals in the aqueous phase, which results in a concentration-dependent inhibition period similar to that of Trolox or cysteine.
| Targets |
NF-κB
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| ln Vitro |
4-Aminosalicylate reacts promptly with DPPH, suggesting a potent radical scavenger activity. The water-soluble 2,2'-azobis-(2-amidinopropane hydrochloride) azoinitiator of peroxyl radicals produces 4-aminosalicylate, which demonstrates peroxyl radical scavenging activity by inhibiting the oxygen consumption or fluorescence decay of cis-parinaric acid. In the aqueous phase, 4-aminosalicylate quickly scavenges peroxyl radicals, resulting in a concentration-dependent inhibition period akin to that of Trolox or cysteine and pointing to an antioxidant activity of the chain-breaking type. [1] [14C] In activated mononuclear cells and activated granulocytes, 4-aminosalicylate converts to a variety of metabolites, of which we have characterized salicylate and gentisate. On cultured Chinese hamster ovary cells, the addition of either superoxide radical or hydrogen peroxide has a lethal effect that is lessened by the addition of 4-aminosalicylate (0.65 mM).[2] In cultured mouse peritoneal macrophages, aminosalicylate (25 mM) stimulates phospholipase D via a pathway involving inositol 1,4,5-trisphosphate generation, calcium fluxes, and Gi/Go. After treating macrophages with 4-aminosalicylate (20 mM), inositol 1,4,5-trisphosphate levels increased by 260%. In cultured mouse peritoneal macrophages, the activation of PLD by protein kinase C is enhanced by the presence of 4-aminosalicylate (5 mM). [3] In isolated colonic mucosal cells, 4-aminosalicylate (0.1 mM) reduces LTB4 synthesis in a dose-dependent manner, lowering the LTB4/PGE2 ratio. [4] The N-acetyl metabolite of 4-aminosalicylate (0.1 mg/mL) only appeared in the apical compartment, and it is preferentially transported in the BL to AP direction. [5]
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| ln Vivo |
4-aminosalicylate (7.5 mg/mL, regional perfusions) results in the anesthetized rat's intestinal lumen containing N-acetyl-5-aminosalicylic acid. [5]
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| Additional Infomation |
Aminosalicylate Sodium is the sodium salt form of aminosalicylic acid, an analog of para-aminobenzoic acid (PABA) with antitubercular activity. Aminosalicylate sodium exerts its bacteriostatic activity against Mycobacterium tuberculosis by competing with PABA for enzymes involved in folate synthesis, thereby suppressing growth and reproduction of M. tuberculosis, eventually leading to cell death.
An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid. See also: Aminosalicylate sodium; aminosalicylic acid (component of). |
| Molecular Formula |
C7H7NO3.2H2O.NA
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| Molecular Weight |
211.15
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| Exact Mass |
211.045
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| CAS # |
6018-19-5
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| Related CAS # |
4-Aminosalicylic acid;65-49-6
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| PubChem CID |
16211148
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| Appearance |
Solid
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| Boiling Point |
380.8ºC at 760 mmHg
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| Melting Point |
250 °C
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| Flash Point |
184.1ºC
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
14
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| Complexity |
165
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[Na+].O([H])C1C([H])=C(C([H])=C([H])C=1C(=O)[O-])N([H])[H].O([H])[H].O([H])[H]
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| InChi Key |
GMUQJDAYXZXBOT-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C7H7NO3.Na.2H2O/c8-4-1-2-5(7(10)11)6(9)3-4;;;/h1-3,9H,8H2,(H,10,11);;2*1H2/q;+1;;/p-1
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| Chemical Name |
sodium;4-amino-2-hydroxybenzoate;dihydrate
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.84 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (11.84 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.84 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (473.60 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7360 mL | 23.6798 mL | 47.3597 mL | |
| 5 mM | 0.9472 mL | 4.7360 mL | 9.4719 mL | |
| 10 mM | 0.4736 mL | 2.3680 mL | 4.7360 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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