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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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| References |
| Molecular Formula |
C7H7NO3.2H2O.NA
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| Molecular Weight |
211.15
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| Exact Mass |
211.04566670
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| CAS # |
6018-19-5
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| Related CAS # |
4-Aminosalicylic acid;65-49-6
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| Appearance |
Solid
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| SMILES |
C1=CC(=C(C=C1N)O)C(=O)[O-].O.O.[Na+]
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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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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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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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| 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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