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Nalidixic acid, also known as 7-methyl-1-ethyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid or acidenalidixico, is a chemical compound. This compound exists as a white to off-white powder, which is almost odorless and has a slightly bitter taste. It is soluble in chloroform, slightly soluble in ethanol and strong alkaline solutions, but almost insoluble in water and ether. It is sensitive to light and air.It works by inhibiting bacterial DNA gyrase, an enzyme essential for bacterial DNA replication, transcription, and repair. By interfering with these processes, it prevents the bacteria from growing and multiplying.
As the first-generation quinolone antibiotic, it has a limited antibacterial spectrum. It is active against some strains of Gram-negative bacteria, such as Escherichia coli, Klebsiella species, Proteus species, Salmonella species, Enterobacter species, and Haemophilus influenzae, as well as Neisseria gonorrhoeae. However, it is not active against Gram-positive bacteria, including Pseudomonas species, Acinetobacter species, and Staphylococcus species.
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| Chemical Formula | C12H12N2O3 |
| Exact Mass | 232.08 |
| Molecular Weight | 232.24 |
| m/z | 232.08 (100.0%), 233.09 (13.0%) |
| Elemental Analysis | C, 62.06; H, 5.21; N, 12.06; O, 20.67 |
As the first generation quinolone antibacterial drug, nalidixic acid has played an important role in the treatment of urinary tract infections since its emergence in the 1960s. It exerts bactericidal effects by inhibiting bacterial DNA gyrase activity, interfering with bacterial DNA replication and repair processes.
Core indication: Precise treatment of urinary tract infections caused by sensitive bacteria
Mainly used to treat urinary tract infections caused by sensitive gram-negative bacteria, including various types such as simple cystitis, pyelonephritis, and complex urinary tract infections.
Simple cystitis: As the most common form of urinary tract infection, it rapidly kills pathogenic bacteria through high urine concentration (peak urine concentration of 150-200mg/L 3-4 hours after administration). A clinical study conducted by the Department of Urology at Peking University First Hospital showed that the effective rate of standardized use of product in treating simple cystitis exceeded 85%, significantly alleviating symptoms such as frequent urination, urgency, and pain.
Pyelonephritis: For upper urinary tract infections, it can penetrate into renal tissue through blood drug concentration (peak plasma concentration of 20-50mg/L 2 hours after oral administration of 1g), inhibiting bacterial colonization and reproduction in the renal pelvis.
Complex urinary tract infections: Treatment can still be effective in the presence of complex factors such as urinary obstruction, stones, or indwelling catheterization. For example, for complex urinary tract infections caused by Escherichia coli, Klebsiella pneumoniae, or Proteus mirabilis, a 5-day course of treatment can achieve control of mild to moderate infections.
Targeted antibacterial spectrum: covering common urinary tract pathogens
Its antibacterial spectrum focuses on Gram negative bacteria, especially highly sensitive to the following pathogens:
Escherichia coli: As the most common pathogenic bacterium in urinary tract infections (accounting for 70% -95% of community-acquired urinary tract infections), it was once the preferred treatment drug. Although the drug resistance rate has increased in recent years (reaching 30% -50% in some areas), it can still be used as a first-line option in cases where drug susceptibility testing confirms sensitivity.
Klebsiella genus: including Klebsiella pneumoniae and Klebsiella acidophilus, often causing hospital acquired urinary tract infections. The MIC value is usually below 4mg/L, indicating good antibacterial activity.
Proteus genus: Proteus mirabilis is the third most common pathogen of urinary tract infections, which can block bacterial division and reproduction by inhibiting its DNA gyrase.
Enterobacteriaceae and Shigella: In patients with urinary tract infections complicated with intestinal infections, they can simultaneously control pathogenic bacteria in the intestinal and urinary systems.
It should be noted that it is naturally resistant to Pseudomonas aeruginosa and has no antibacterial activity against gram-positive cocci (such as Staphylococcus aureus and Enterococcus), so precise medication should be based on pathogen results.
Special scenario application: Expanding treatment boundaries
Showcasing unique value in specific clinical scenarios:
Supplementary treatment for drug-resistant bacterial infections: In areas where multidrug-resistant bacteria are prevalent, when other antibiotics (such as third-generation cephalosporins and carbapenems) fail due to resistance issues, acidenalidixico can be used as part of a combination therapy regimen to enhance efficacy through synergistic effects.
Postoperative urinary tract infection prevention: After urological surgery (such as transurethral resection of the prostate and nephrectomy), the incidence of infection can be reduced by inhibiting the colonization of pathogenic bacteria at the surgical site. The preventive medication regimen usually starts one day before surgery, three times a day, and lasts until 3-5 days after surgery.
Naphthalene acid has become an important tool for the treatment of urinary tract infections due to its precise antibacterial spectrum, flexible medication regimen, and unique value in special scenarios. Despite facing resistance challenges, it can still provide safe and effective treatment options for patients through rational use, such as strictly controlling indications, selecting drugs based on drug sensitivity results, and standardizing treatment duration and dosage.
Research Cases
1. Antibacterial Activity
Primarily used to treat urinary tract infections, intestinal infections, and skin infections by inhibiting the activity of DNA gyrase, an enzyme crucial for bacterial DNA replication, repair, and recombination. Research has shown that it effectively inhibits the growth of common pathogenic Gram-negative bacteria, including Escherichia coli, Salmonella, Klebsiella pneumoniae, Proteus, and Pseudomonas, which are the main culprits of clinical superficial and systemic bacterial infections. Studies in mouse models and laboratory environments have fully confirmed its stable antibacterial efficacy against drug-sensitive Escherichia coli, verifying its reliable therapeutic effect in targeted bacterial infection treatment.
2. Gene Editing Tool
Recent research has discovered that nalidixic acid can be utilized as an efficient auxiliary gene editing tool, enabling the precise knockout or targeted modification of specific gene expression in prokaryotic and partial eukaryotic cells. This innovative technique is defined as "chemical genomics" or "small-molecule genomics", filling the technical gap of small-molecule assisted gene regulation. By combining with the mature CRISPR-Cas9 system, researchers can effectively reduce editing errors, more precisely control gene expression levels, and further deepen the exploration and understanding of core gene functions in complex biological processes.
3. Anticancer Activity
Acidenalidixico has demonstrated obvious anticancer activity by significantly inhibiting the proliferation growth and metastatic spread of certain malignant cancer cells. Existing studies indicate that this anticancer effect is closely related to its specific inhibition of DNA gyrase activity, which can block the DNA replication process of cancer cells and induce cancer cell apoptosis. Currently, researchers are actively exploring its pharmacological mechanism and clinical potential as a novel anticancer drug, hoping to optimize its efficacy and reduce toxicity through further in-depth research.
4. Bioimaging Agent
Due to its stable inherent fluorescent properties under specific excitation conditions, acidenalidixico can be used as a low-toxicity bioimaging agent to intuitively label and track living cells, functional proteins and DNA molecules in real time. This efficient fluorescence labeling technique greatly aids researchers in dynamically observing and analyzing the behavioral changes and functional mechanisms of biomolecules, providing accurate and reliable experimental data support for subsequent targeted drug design and precise disease treatment research.
1. Expanded Antibacterial Spectrum
With ongoing in-depth pharmacological and bacteriological research, acidenalidixico is expected to be optimized and developed to treat infectious diseases caused by a broader spectrum of pathogens. Subsequent modification of its molecular structure may enable it to exert inhibitory effects on typical Gram-positive bacteria, and even expand its antimicrobial activity to partial viruses and fungi, breaking its traditional single antibacterial application scope.
2. Advancements in Gene Editing
As a novel auxiliary gene editing tool, it has huge application potential to drive technological breakthroughs in fields such as precision gene therapy and individualized personalized medicine.Its unique advantages in precise regulation and stable control of gene expression make it a highly valuable research tool and clinical auxiliary technology in life science research and translational medical applications.
3. Novel Anticancer Therapies
The verified anticancer activity of acidenalidixico brings new research directions and therapeutic hope for clinical cancer patients.With continuous exploration of its anticancer mechanism and pharmacological optimization, it is expected to be developed into a new targeted anticancer drug, which can accurately act on specific cancer cells and effectively reduce damage to normal human cells, minimizing clinical side effects.
4. Biomedical Research and Applications
Its application as a biomolecular tool has been gradually extended to the research and construction of artificial nucleases and DNA molecular motors, covering multiple emerging fields such as targeted drug delivery, precise gene therapy and bionanotechnology. By reasonably combining it with other functional molecular components, researchers can design and build artificial molecular machines with specific biological functions, opening up new innovative directions for basic biomedical research and industrial transformation applications.
Preparation & Synthesis
Initial Synthesis Step
Start with 2-methylpyridine to produce 2-amino-5-methylpyridine.
Condensation Reaction
React 2-amino-5-methylpyridine with ethyl orthoformate and diethyl malonate to form N-(2-methyl-5-aminopyridyl)malonic acid diethyl ester.
Cyclization
Subject the intermediate product to cyclization at a temperature range of 260-270°C.
Hydrolysis
Add the cyclized product to a dilute sodium hydroxide solution for hydrolysis, yielding 7-methyl-1,8-naphthyridin-4-ol-3-carboxylic acid.
N-Alkylation and Isomerization
Treat the resulting acid with ethyl bromide to undergo N-alkylation, followed by isomerization, to produce nalidixone acid.
The discovery of nalidixic acid indeed signifies a pivotal moment in the progression of quinolone antibiotics. The story begins in 1946 when Dr. George Lesher, an organic chemist employed at the Sterling Winthrop Research Institute, serendipitously encountered it as an unintended byproduct while synthesizing chloroquine. This fortunate accident led to a series of routine screenings, during which Dr. Lesher recognized its potential antibacterial properties.
Fast forward to 1962, Dr. Lesher's suspicions were confirmed through rigorous testing, solidifying its status as an antibacterial agent.
This groundbreaking discovery prompted Sterling Pharmaceuticals to file for a patent in 1963, which was granted, followed by a public announcement in 1964.
This announcement marked the official introduction to the scientific community and the medical world, heralding a new era in antibiotic therapy with quinolones.
Its journey from an accidental byproduct to a revolutionary antibiotic underscores the unpredictable nature of scientific discovery and the profound impact it can have on human health and medical practice.
FAQ
What is nalidixic acid used to treat?
Nalidixic acid is a narrow-spectrum agent against enteric bacteria used for treating uncomplicated urinary tract infections (UTIs). During the 1970s–1980s, the coverage of the quinolone class was expanded significantly by the breakthrough development of fluoroquinolones.
Why was nalidixic acid discontinued?
Nalidixic acid, the first quinolone antibiotic, was discovered in 1962. It is used principally for the treatment of urinary tract infections. Its use has declined due to the development of bacterial resistance and the availability of more potent derivatives with a broader spectrum, such as ciprofloxacin.
What is the brand name for nalidixic acid?
Nalidixic acid (tradenames Nevigramon, NegGram, Wintomylon and WIN 18,320) is the first of the synthetic quinolone antibiotics.
How long should I take nalidixic acid?
Initial therapy: 1 g orally 4 times a day for 1 or 2 weeks. Prolonged therapy: May reduce to 2 g/day after initial therapy.
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