Ácido nalidíxico

Número de catálogo: B1676918

Número CAS: 389-08-2

Peso molecular: 232.23 g/mol

Clave InChI: MHWLWQUZZRMNGJ-UHFFFAOYSA-N

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Descripción general

1. Descripción

7. Comparación con compuestos similares

2. Mecanismo de acción

8. Propiedades

3. Aplicaciones científicas de investigación

9. Synthesis routes and methods I

4. Análisis bioquímico

10. Synthesis routes and methods II

5. Métodos de preparación

11. Retrosynthesis analysis

6. Análisis de reacciones químicas

12. Descargo de responsabilidad

Descripción

El ácido nalidíxico, también conocido por sus nombres comerciales Nevigramon, NegGram, Wintomylon y WIN 18,320, es el primer antibiótico quinolónico sintético.
Técnicamente, pertenece a la clase de las naftiridonas en lugar de la clase de las quinolonas. Su estructura cíclica es un núcleo de 1,8-naftiridina que contiene dos átomos de nitrógeno, a diferencia de la quinolina, que solo tiene un átomo de nitrógeno .

Mecanismo De Acción

El ácido nalidíxico inhibe la ADN girasa bacteriana (topoisomerasa II), evitando la replicación y transcripción del ADN.
Interfiere con la superenrollamiento del ADN, lo que lleva a la muerte celular.
Los objetivos moleculares del compuesto son las topoisomerasas bacterianas .

Aplicaciones Científicas De Investigación

El ácido nalidíxico se utiliza principalmente para tratar infecciones del tracto urinario causadas por bacilos gramnegativos sensibles (por ejemplo, Escherichia coli, Klebsiella spp.).
Debido a la creciente resistencia, es esencial seleccionar antibióticos según los resultados de las pruebas de susceptibilidad .

Análisis Bioquímico

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 .

Métodos De Preparación

El ácido nalidíxico se sintetiza a partir de 2-metilpiridina para formar 2-amino-5-metilpiridina.
El último compuesto se condensa luego con formiato de etilo y oxalato de dietilo para producir N-(2-metil-5-amino-piridina)metilen malonato.
La ciclación a 260-270 °C seguida de hidrólisis con hidróxido de sodio produce ácido 7-metil-1,8-naftiridina-4-hidroxi-3-carboxílico.
Finalmente, la N-alquilación con bromoetano conduce al ácido nalidíxico .

Análisis De Reacciones Químicas

El ácido nalidíxico exhibe actividad antibacteriana contra bacterias gramnegativas y algunas grampositivas.
Actúa bacteriostáticamente a concentraciones más bajas y bactericidamente a concentraciones más altas.
Las reacciones comunes incluyen hidrólisis, alquilación y oxidación.
Los principales productos formados incluyen ácido 7-metil-1,8-naftiridina-4-hidroxi-3-carboxílico y sus derivados .

Comparación Con Compuestos Similares

El ácido nalidíxico es único debido a su estructura de naftiridona.
Compuestos similares incluyen otras quinolonas como ciprofloxacina, levofloxacina y moxifloxacina .

Propiedades

IUPAC Name	1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid	Source
Source	PubChem
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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
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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]
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DSSTOX Substance ID	DTXSID3020912	Source
Record name	Nalidixic acid
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Molecular Weight	232.23 g/mol	Source
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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
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Record name	Nalidixic Acid
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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
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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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Color/Form	PALE BUFF, CRYSTALLINE POWDER, WHITE TO SLIGHTLY YELLOW, CRYSTALLINE POWDER
CAS No.	389-08-2	Source
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Melting Point	444 to 446 °F (NTP, 1992), 229-230 °C, 229.5 °C	Source
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Synthesis routes and methods I

Procedure details

The culture medium LB (Tryptone 10 g/L, yeast extract 5 g/L, NaCl 10 g/L) that once autoclaved was supplemented with 25 μg/mL of kanamycin was used to grow E. coli S17-1 λ pir. Once the stationary phase was achieved, 0.2-0.3 A600 units of the App culture and 0.6-0.8 A600 units of the E. coli culture were added to 1 mL of a 10 mM solution of MgSO4. Next it was centrifuged during 2 minutes at 15,000 g and the pellet so obtained was resuspended in 200 μl of a 10 mM MgSO4 solution. Once the mixture of both cultures had been done, this was extended on a 2.5 cm and 0.45 μM nitrocellulose filter previously placed on a Petri dish containing TSYN medium supplemented with 15 g/L Noble agar. After incubation during 6 hours at 37 C., the filter with the conjugation was placed in a tube containing 2 mL of PBS (Na2HPO410 mM, KH2PO4 1 mM, NaCl 137 mM, KCl 2 mM pH 7.4). After vigorous shaking, the filter was removed and the cell suspension was centrifuged during 2 minutes at 15,000 g and the pellet was resuspended in 500 μL of PBS. The so obtained suspension was distributed in Petri dishes with TSYN medium supplemented with 15 g/L Noble Agar, 50 μg/mL kanamycin and 50 μg/mL nalidixic acid, at a rate of 100 μL of cell suspension for each Petri dish. The resulting cultures were incubated at 37 C. for 24-36 hours. With this procedure 65 colonies resistant to kanamicin and nalidixic acid, were obtained for the conjugation with the plasmid pApxIΔH2, which equals a frequency of transformation of 1.3×10−7 for each receptor cell.

Name

MgSO4

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

[Compound]

Name

nitrocellulose

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0 (± 1) mol

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reactant

Reaction Step Two

Name

kanamycin

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0 (± 1) mol

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reactant

Reaction Step Three

Name

nalidixic acid

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0 (± 1) mol

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reactant

Reaction Step Four

Name

kanamicin

Name

nalidixic acid

Details

Synthesis routes and methods II

Procedure details

85 mutant strains obtained above were inoculated in a 8 ml LB medium containing 50 μg/ml ampicillin in a large test tube, and cultured at 30° C. for 17 hr. The culture medium was inoculated at 1% in a 8 ml medium containing 100 μg/ml ampicillin [16 g/L dipotassium hydrogen phosphate, 14 g/L potassium dihydrogen phosphate, 5 g/L ammonium sulfate, 1 g/L citric acid (anhydrous), 5 g/L casamino acid (manufactured by Difco), 10 g/L glucose, 10 mg/L vitamin B1, 25 mg/L magnesium sulfate heptahydrate, 50 mg/L iron sulfate heptahydrate, 100 mg/L L-proline, adjusted with 10 mol/L sodium hydroxide to pH 7.2, and glucose, vitamin B1, magnesium sulfate heptahydrate and iron sulfate heptahydrate were separately autoclaved and added] in a test tube, and cultured at 30° C. for 24 hr. The culture medium was centrifuged and a culture supernatant was obtained. The accumulated amounts of L-glutamine and L-glutamic acid in the culture supernatant were quantified by high performance liquid chromatography (HPLC), and productivity of L-glutamine and L-glutamic acid was evaluated.

Name

ampicillin

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reactant

Reaction Step One

Name

sodium hydroxide

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Name

glucose

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reactant

Reaction Step Three

Name

vitamin B1

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0 (± 1) mol

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reactant

Reaction Step Four

Name

magnesium sulfate heptahydrate

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reactant

Reaction Step Five

Name

L-glutamine

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reactant

Reaction Step Six

Name

L-glutamic acid

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reactant

Reaction Step Seven

Name

L-glutamine

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reactant

Reaction Step Eight

Name

L-glutamic acid

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0 (± 1) mol

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reactant

Reaction Step Nine

Name

iron sulfate heptahydrate

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0 (± 1) mol

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catalyst

Reaction Step Ten

Name

ampicillin

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reactant

Reaction Step Eleven

Name

dipotassium hydrogen phosphate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Eleven

Name

potassium dihydrogen phosphate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Eleven

Name

ammonium sulfate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Eleven

Name

citric acid

Quantity

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reactant

Reaction Step Eleven

Name

glucose

Quantity

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Type

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Reaction Step Eleven

Name

vitamin B1

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reactant

Reaction Step Eleven

Name

magnesium sulfate heptahydrate

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0 (± 1) mol

Type

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Reaction Step Eleven

Name

L-proline

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0 (± 1) mol

Type

reactant

Reaction Step Eleven

Name

iron sulfate heptahydrate

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0 (± 1) mol

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catalyst

Reaction Step Eleven

Name

Nalidixic Acid

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Nalidixic acid

Reactant of Route 2

Nalidixic acid

Reactant of Route 3

Nalidixic acid

Reactant of Route 4

Nalidixic acid

Reactant of Route 5

Nalidixic acid

Reactant of Route 6

Nalidixic acid

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