Nalidixsäure
Übersicht
Beschreibung
- Nalidixinsäure, auch bekannt unter den Handelsnamen Nevigramon, NegGram, Wintomylon und WIN 18,320, ist das erste synthetische Chinolon-Antibiotikum.
- Technisch gesehen gehört es zur Klasse der Naphthyridone und nicht zur Klasse der Chinolone. Seine Ringstruktur ist ein 1,8-Naphthyridin-Kern, der zwei Stickstoffatome enthält, im Gegensatz zu Chinolin, das nur ein Stickstoffatom hat .
Wirkmechanismus
Target of Action
Nalidixic acid, a synthetic 1,8-naphthyridine antimicrobial agent, primarily targets the A subunit of bacterial DNA gyrase . DNA gyrase is an essential enzyme that introduces negative supercoils (or relaxes positive supercoils) in DNA, facilitating replication and transcription processes in bacteria .
Mode of Action
Nalidixic acid’s active metabolite, hydroxynalidixic acid , binds strongly but reversibly to DNA . This binding interferes with the synthesis of RNA, and consequently, with protein synthesis . By inhibiting DNA gyrase, nalidixic acid prevents the unwinding of DNA, thereby inhibiting bacterial DNA replication .
Biochemical Pathways
The inhibition of DNA gyrase by nalidixic acid affects the DNA replication pathway in bacteria. This disruption of DNA replication prevents the bacteria from multiplying and growing, leading to a bacteriostatic effect at lower concentrations . At higher concentrations, nalidixic acid can have a bactericidal effect, killing the bacteria instead of merely inhibiting their growth .
Pharmacokinetics
Following oral administration, nalidixic acid is rapidly absorbed from the gastrointestinal tract . It reaches peak blood concentrations in two to four hours . The daily urinary recovery of the administered drug is approximately 80% at steady state . Nalidixic acid is partially metabolized in the liver and has an elimination half-life of 6-7 hours, which can be significantly longer in cases of renal impairment .
Result of Action
Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri . It is used clinically to treat urinary tract infections caused by these susceptible gram-negative microorganisms .
Wissenschaftliche Forschungsanwendungen
- Nalidixinsäure wird hauptsächlich zur Behandlung von Harnwegsinfektionen verwendet, die durch empfindliche gramnegative Stäbchen (z. B. Escherichia coli, Klebsiella spp.) verursacht werden.
- Aufgrund zunehmender Resistenz ist es wichtig, Antibiotika auf der Grundlage von Empfindlichkeitstests auszuwählen .
Wirkmechanismus
- Nalidixinsäure hemmt die bakterielle DNA-Gyrase (Topoisomerase II) und verhindert so die DNA-Replikation und -Transkription.
- Sie stört die DNA-Supercoiling, was zum Zelltod führt.
- Die molekularen Zielstrukturen der Verbindung sind bakterielle Topoisomerasen .
Biochemische Analyse
Biochemical Properties
Nalidixic acid plays a crucial role in biochemical reactions by targeting bacterial DNA gyrase and topoisomerase IV, enzymes essential for DNA replication and transcription. By inhibiting these enzymes, nalidixic acid prevents the supercoiling and uncoiling of bacterial DNA, thereby halting DNA synthesis. This interaction is specific to bacterial enzymes, making nalidixic acid effective against bacterial infections while having minimal impact on human cells .
Cellular Effects
Nalidixic acid exerts significant effects on various types of cells, particularly bacterial cells. It disrupts cell function by inhibiting DNA synthesis, leading to cell death. In bacterial cells, nalidixic acid affects cell signaling pathways, gene expression, and cellular metabolism. The inhibition of DNA gyrase and topoisomerase IV results in the accumulation of DNA breaks, which triggers the bacterial SOS response and ultimately leads to cell death .
Molecular Mechanism
The molecular mechanism of nalidixic acid involves its binding to the A subunit of DNA gyrase and the C subunit of topoisomerase IV. This binding interferes with the enzymes’ ability to introduce negative supercoils into DNA, which is essential for DNA replication and transcription. By stabilizing the DNA-enzyme complex, nalidixic acid prevents the re-ligation of DNA strands, leading to the accumulation of DNA breaks and inhibition of bacterial growth .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of nalidixic acid change over time. Initially, nalidixic acid rapidly inhibits DNA synthesis, leading to a decrease in bacterial growth. Over time, the stability and degradation of nalidixic acid can influence its effectiveness. Studies have shown that nalidixic acid is relatively stable under laboratory conditions, but prolonged exposure can lead to the development of bacterial resistance .
Dosage Effects in Animal Models
The effects of nalidixic acid vary with different dosages in animal models. At therapeutic doses, nalidixic acid effectively treats bacterial infections without causing significant toxicity. At high doses, nalidixic acid can exhibit toxic effects, including gastrointestinal disturbances and central nervous system toxicity. Threshold effects have been observed, where increasing the dosage beyond a certain point does not significantly enhance its antibacterial activity but increases the risk of adverse effects .
Metabolic Pathways
Nalidixic acid is metabolized in the liver, primarily through hydroxylation to form hydroxynalidixic acid. This metabolite retains antibacterial activity and contributes to the overall effectiveness of nalidixic acid. The metabolic pathways involve enzymes such as cytochrome P450, which facilitate the conversion of nalidixic acid to its active metabolite. The presence of hydroxynalidixic acid in the bloodstream ensures sustained antibacterial activity .
Transport and Distribution
Nalidixic acid is transported and distributed within cells and tissues through passive diffusion. It can cross cell membranes and accumulate in bacterial cells, where it exerts its antibacterial effects. The distribution of nalidixic acid within tissues is influenced by factors such as blood flow and tissue permeability. Transporters and binding proteins may also play a role in the cellular uptake and distribution of nalidixic acid .
Subcellular Localization
Nalidixic acid primarily localizes in the cytoplasm of bacterial cells, where it interacts with DNA gyrase and topoisomerase IV. The subcellular localization of nalidixic acid is crucial for its antibacterial activity, as it needs to reach its target enzymes to inhibit DNA synthesis. Post-translational modifications and targeting signals may influence the localization and activity of nalidixic acid within bacterial cells .
Vorbereitungsmethoden
- Nalidixinsäure wird aus 2-Methylpyridin zu 2-Amino-5-Methylpyridin synthetisiert.
- Die letztere Verbindung wird dann mit Ameisensäureethylester und Diethyloxalat kondensiert, um N-(2-Methyl-5-Amino-pyridin)methylenmalonat zu erzeugen.
- Die Cyclisierung bei 260-270 °C, gefolgt von der Hydrolyse mit Natriumhydroxid, ergibt 7-Methyl-1,8-naphthyridin-4-hydroxy-3-carbonsäure.
- Schließlich führt die N-Alkylierung mit Bromethan zu Nalidixinsäure .
Analyse Chemischer Reaktionen
- Nalidixinsäure zeigt antibakterielle Aktivität gegen sowohl gramnegative als auch einige grampositive Bakterien.
- Sie wirkt bakteriostatisch bei niedrigeren Konzentrationen und bakterizid bei höheren Konzentrationen.
- Häufige Reaktionen umfassen Hydrolyse, Alkylierung und Oxidation.
- Zu den wichtigsten gebildeten Produkten gehören 7-Methyl-1,8-naphthyridin-4-hydroxy-3-carbonsäure und ihre Derivate .
Vergleich Mit ähnlichen Verbindungen
- Nalidixinsäure ist aufgrund ihrer Naphthyridon-Struktur einzigartig.
- Ähnliche Verbindungen umfassen andere Chinolone wie Ciprofloxacin, Levofloxacin und Moxifloxacin .
Eigenschaften
IUPAC Name |
1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
MHWLWQUZZRMNGJ-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H12N2O3 |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
3374-05-8 (hydrochloride salt, anhydrous) |
Source
|
| Record name | Nalidixic acid [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000389082 | |
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DSSTOX Substance ID |
DTXSID3020912 |
Source
|
| Record name | Nalidixic acid | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3020912 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
232.23 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Nalidixic acid is a cream-colored powder. (NTP, 1992), Solid |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
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| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014917 | |
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Solubility |
less than 1 mg/mL at 70 °F (NTP, 1992), Soly at 23 °C (mg/ml): chloroform 35; toluene 1.6; methanol 1.3; ethanol 0.6; water 0.1; ether 0.1., PRACTICALLY INSOL IN WATER; SOL IN SOLN OF CARBONATES, 2.30e+00 g/L |
Source
|
| Record name | NALIDIXIC ACID | |
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| Record name | Nalidixic acid | |
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| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
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Mechanism of Action |
Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis., IT APPEARS TO ACT BY INHIBITING DNA SYNTH. |
Source
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| Record name | Nalidixic acid | |
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Color/Form |
PALE BUFF, CRYSTALLINE POWDER, WHITE TO SLIGHTLY YELLOW, CRYSTALLINE POWDER | |
CAS No. |
389-08-2 |
Source
|
| Record name | NALIDIXIC ACID | |
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Melting Point |
444 to 446 °F (NTP, 1992), 229-230 °C, 229.5 °C |
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|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
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| Source | Human Metabolome Database (HMDB) | |
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Synthesis routes and methods I
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Synthesis routes and methods II
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Retrosynthesis Analysis
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