Pyridoxine
Descripción general
Descripción
La piridoxina, comúnmente conocida como vitamina B6, es una vitamina soluble en agua que juega un papel crucial en diversas funciones biológicas. Se encuentra naturalmente en muchos alimentos y también está disponible como suplemento dietético. La piridoxina es esencial para el metabolismo de los aminoácidos, los carbohidratos y los lípidos, y apoya la salud del cerebro, la función inmunitaria y la síntesis de neurotransmisores .
Métodos De Preparación
Rutas sintéticas y condiciones de reacción: La piridoxina se puede sintetizar mediante varios métodos. Un enfoque común implica la condensación de cianoacetamida con compuestos 1,3-dicarbonílicos. Otro método utiliza la condensación de derivados de 1,3-oxazol con dienófilos, seguida de hidrogenación catalítica . Estos métodos se caracterizan por altos rendimientos y condiciones de reacción suaves.
Métodos de producción industrial: La producción industrial de piridoxina generalmente implica el método "oxazol", que es un proceso de dos etapas. La primera etapa involucra la condensación de dienos para formar compuestos intermedios, que luego se convierten en piridoxina mediante hidrogenación catalítica . Este método se usa ampliamente debido a su eficiencia y rentabilidad.
Análisis De Reacciones Químicas
Tipos de reacciones: La piridoxina experimenta varias reacciones químicas, incluida la oxidación, la reducción y la sustitución. Se puede oxidar selectivamente para formar piridoxal o clorhidrato de piridoxal utilizando un sistema de oxidación catalítica .
Reactivos y condiciones comunes: Los reactivos comunes utilizados en la oxidación de la piridoxina incluyen fuentes de oxígeno, catalizadores, sales inorgánicas y ligandos de amina. Las reacciones generalmente se llevan a cabo en agua como disolvente en condiciones suaves .
Productos principales: Los principales productos formados a partir de la oxidación de la piridoxina son el piridoxal y el clorhidrato de piridoxal, que son intermediarios clave en la síntesis de piridoxal 5'-fosfato, la forma activa de coenzima de la vitamina B6 .
Aplicaciones Científicas De Investigación
Biochemical Functions and Mechanisms
Pyridoxine is essential for over 100 enzymatic reactions, primarily as a precursor to its active form, pyridoxal 5'-phosphate (PLP). These reactions include:
- Amino Acid Metabolism : PLP is vital for transamination reactions, which are critical in amino acid synthesis and degradation.
- Neurotransmitter Synthesis : this compound is involved in the production of neurotransmitters such as serotonin, dopamine, and gamma-aminobutyric acid (GABA) .
- Glycogenolysis and Gluconeogenesis : It facilitates the conversion of glycogen to glucose and the synthesis of glucose from non-carbohydrate sources .
Clinical Applications
This compound is primarily used in clinical settings for:
- Treatment of Vitamin B6 Deficiency : This condition can lead to anemia, peripheral neuropathy, and immune dysfunction. This compound supplementation is crucial for affected individuals .
- Isoniazid-Induced Peripheral Neuropathy Prophylaxis : Patients on isoniazid for tuberculosis treatment often require this compound to prevent peripheral nerve damage caused by the drug .
- Nausea and Vomiting in Pregnancy : this compound is used in combination with doxylamine (Diclectin) to manage nausea during pregnancy .
Research Applications
Recent studies have highlighted the potential of this compound and its derivatives in various disease contexts:
- Cancer Research : this compound's anti-inflammatory and antioxidant properties have been linked to cancer prevention and management strategies .
- Metabolic Disorders : Research indicates that alterations in this compound metabolism may contribute to conditions like diabetes and hypertension .
- Neurodegenerative Diseases : Studies suggest that this compound may play a protective role against neurodegeneration through its involvement in neurotransmitter synthesis .
Analytical Methods for this compound Determination
The determination of this compound levels in pharmaceutical formulations has been achieved through various electroanalytical techniques. A notable method involves using a copper(II) hexacyanoferrate(III) modified carbon paste electrode, which demonstrated high sensitivity and selectivity for this compound detection .
Table 1: Analytical Methods for this compound Detection
| Method | Detection Limit | Application Area |
|---|---|---|
| Cyclic Voltammetry | Pharmaceutical formulations | |
| Spectrophotometry | Varies | Nutritional analysis |
| High-Performance Liquid Chromatography (HPLC) | Varies | Clinical diagnostics |
Case Studies
Several case studies illustrate the practical applications of this compound:
- Case Study 1 : A study involving patients with chronic kidney disease showed that supplementation with this compound improved metabolic profiles and reduced symptoms related to vitamin B6 deficiency.
- Case Study 2 : Research on pregnant women indicated significant reductions in nausea when treated with a combination of this compound and doxylamine compared to placebo groups.
Mecanismo De Acción
La piridoxina se convierte en piridoxal 5'-fosfato en el cuerpo, que actúa como coenzima en varias reacciones bioquímicas. Está involucrada en el metabolismo de los aminoácidos, el glucógeno y los lípidos, y ayuda en la síntesis de neurotransmisores como la serotonina, la dopamina, la noradrenalina y el ácido gamma-aminobutírico (GABA) . El piridoxal 5'-fosfato también juega un papel en la síntesis de hemoglobina y esfingolípidos .
Comparación Con Compuestos Similares
La piridoxina es parte del grupo de la vitamina B6, que incluye piridoxal y piridoxamina, junto con sus derivados fosforilados. Estos compuestos son químicamente similares y pueden interconvertirse en sistemas biológicos . El piridoxal 5'-fosfato tiene la mayor actividad biológica entre estos compuestos, pero todas las formas son esenciales para varias reacciones enzimáticas .
Compuestos similares:
- Piridoxal
- Piridoxamina
- Piridoxina 5'-fosfato
- Piridoxal 5'-fosfato
- Piridoxamina 5'-fosfato
La piridoxina es única en su estabilidad y es la forma más utilizada en los suplementos dietéticos .
Actividad Biológica
Pyridoxine, also known as Vitamin B6, is a water-soluble vitamin that plays a crucial role in numerous biochemical processes within the human body. Its biological activity is primarily mediated through its active form, pyridoxal 5'-phosphate (PLP), which serves as a coenzyme in various enzymatic reactions. This article delves into the mechanisms of action, pharmacokinetics, therapeutic applications, and recent research findings related to this compound.
This compound is involved in over 100 enzymatic reactions, primarily related to amino acid metabolism. The following are key mechanisms through which this compound exerts its biological effects:
- Amino Acid Metabolism : PLP acts as a cofactor for enzymes involved in transamination, decarboxylation, and racemization, facilitating the conversion of amino acids into neurotransmitters such as serotonin and dopamine .
- Glycogen Metabolism : this compound is essential for glycogen phosphorylase activity, which is critical for glucose mobilization from glycogen stores .
- Neurotransmitter Synthesis : It plays a vital role in synthesizing neurotransmitters, including gamma-aminobutyric acid (GABA), norepinephrine, and histamine .
Pharmacokinetics
The pharmacokinetics of this compound involves its absorption, distribution, metabolism, and excretion:
- Absorption : this compound is absorbed mainly in the jejunum through passive diffusion. Its bioavailability can be affected by various factors including dietary intake and gastrointestinal health .
- Distribution : The primary active metabolite, PLP, binds to plasma proteins (primarily albumin) and accounts for approximately 60% of circulating vitamin B6 .
- Metabolism : this compound is metabolized in the liver to PLP. This conversion is crucial as PLP is the biologically active form that participates in enzymatic reactions .
- Excretion : Excess this compound is excreted via urine as pyridoxic acid and other metabolites.
Therapeutic Applications
This compound has several clinical applications:
- Vitamin B6 Deficiency : It is primarily used to treat deficiencies that can lead to symptoms such as irritability, depression, and peripheral neuropathy.
- Nausea and Vomiting in Pregnancy : this compound is often combined with doxylamine in medications like Diclectin to alleviate nausea during pregnancy .
- Homocystinuria : High doses of this compound can improve symptoms in certain patients with homocystinuria by enhancing cystathionine synthase activity .
Research Findings
Recent studies have highlighted various aspects of this compound's biological activity:
-
Blood Glucose Regulation : A study assessed the effects of this compound on blood glucose levels in diabetic patients. Results indicated significant decreases in fasting insulin and insulin resistance after four weeks of treatment with this compound .
Parameter Treatment Group Mean ± SD Control Group Mean ± SD Fasting Plasma Glucose (mg/dL) 138.42 ± 5.555 83.53 ± 4.73 Hemoglobin A1C (%) 6.938 ± 0.092 5.12 ± 0.064 -
Homocystinuria Case Studies : In patients with this compound-responsive homocystinuria, administration of high doses (200-500 mg daily) resulted in normalization of plasma methionine and homocystine levels .
- One patient responded positively at a lower dose compared to another patient requiring significantly higher doses, indicating variability in response based on individual metabolic pathways.
- Endothelial Protection : Research has shown that PLP protects vascular endothelial cells from damage caused by activated platelets, suggesting potential cardiovascular benefits associated with adequate this compound levels .
Q & A
Basic Research Questions
Q. How to determine pyridoxine's dietary requirements in avian models?
Methodological Answer:
- Conduct dose-response experiments using vitamin B6-deficient basal diets supplemented with this compound·HCl (e.g., 0–3.99 mg/kg).
- Measure weight gain, feed efficiency, and plasma biomarkers (e.g., homocysteine, aminotransferases) over 28 days.
- Use one-way ANOVA to assess variance and quadratic regression (via SAS REG procedure) to estimate the requirement at 95% of maximum response . Key Data:
| Supplemental this compound (mg/kg) | Weight Gain (g) | Plasma Homocysteine (μmol/L) |
|---|---|---|
| 0 | 570 ± 30 | 28.5 ± 2.1 |
| 3.99 | 850 ± 45 | 12.3 ± 1.8 |
Q. What analytical techniques ensure accurate this compound quantification in complex matrices?
Methodological Answer:
- Extract this compound via hot water and analyze using HPLC with fluorescence detection (e.g., Waters Alliance 2695).
- Validate methods via recovery rates (85–110%) and cross-check with UV-Vis spectrophotometry using robust regression models (e.g., RANSAC for outlier resistance) . Key Parameters:
| HPLC Column | Mobile Phase | Flow Rate | Detection Wavelength |
|---|---|---|---|
| C18 | 0.1% H3PO4 | 1.0 mL/min | Ex: 290 nm, Em: 395 nm |
Q. What are the thermodynamic properties of this compound in aqueous solutions?
Methodological Answer:
- Determine dissociation constants (pK1 = 4.85 ± 0.02, pK2 = 8.96 ± 0.03) via direct calorimetry and equilibrium diagrams.
- Model speciation using computational tools (e.g., "KEV" program) to predict dominant ionic species at varying pH . Speciation Table:
| pH Range | Dominant Form |
|---|---|
| <4.85 | Cationic (H2PN+) |
| 4.85–8.96 | Zwitterionic (HPN±) |
| >8.96 | Anionic (PN−) |
Advanced Research Questions
Q. How to resolve overlapping UV-Vis spectra of this compound in pharmaceutical mixtures?
Methodological Answer:
- Apply robust regression models (Huber, RANSAC, Theil-Sen) to deconvolute spectral overlap (e.g., caffeine and this compound HCl).
- Validate using Wilcoxon rank tests; RANSAC outperforms others with p > 0.05 for this compound predictions . Performance Metrics:
| Model | This compound p-value | Outlier Tolerance |
|---|---|---|
| RANSAC | 0.3125 | High |
| Theil-Sen | 0.3125 | Moderate |
| Huber | 0.4375 | Low |
Q. How to assess this compound's role in Mycobacterium tuberculosis metabolism?
Methodological Answer:
- Characterize enzyme kinetics of this compound 5′-phosphate oxidase (Rv2607) using substrate specificity assays.
- Measure catalytic efficiency (kcat/Km = 1.2 × 10³ M⁻¹s⁻¹) and compare with homologs via bioinformatic analysis . Kinetic Data:
| Substrate | Km (μM) | kcat (s⁻¹) |
|---|---|---|
| This compound 5′-P | 45 ± 3 | 0.54 ± 0.02 |
| Pyridoxamine 5′-P | >500 | Not detected |
Q. How to design pharmacokinetic studies for this compound combination therapies?
Methodological Answer:
- Use crossover bioequivalence studies (e.g., Study 160286) comparing single agents vs. fixed-dose combinations (FDCs).
- Analyze AUC and Cmax ratios (90% CI within 80–125%) under EMA/CHMP guidelines . Pharmacokinetic Outcomes:
| Parameter | This compound Alone | FDC (Doxylamine + this compound) |
|---|---|---|
| AUC₀–24h | 1200 ± 150 ng·h/mL | 1150 ± 140 ng·h/mL |
| Cmax | 85 ± 10 ng/mL | 80 ± 9 ng/mL |
Q. What mechanisms underlie this compound-induced sensory neuropathy?
Methodological Answer:
- Correlate dose-duration effects (0.2–5 g/day) with axonal degeneration via nerve conduction studies.
- Identify susceptibility factors (e.g., pre-existing neuropathy) using case-control designs . Clinical Findings:
| Daily Dose (g) | Symptom Onset (Months) | Improvement Post-Cessation |
|---|---|---|
| 0.2–1 | 12–24 | Partial (6–12 months) |
| >1 | 1–3 | Gradual (3–6 months) |
Q. How to optimize this compound formulations for enhanced stability?
Methodological Answer:
- Test excipient compatibility (e.g., benzenesulfonic acid, glycerol) under accelerated stability conditions (40°C/75% RH).
- Monitor viscosity reduction (30–50%) and degradation products via HPLC-MS . Formulation Data:
| Excipient | Degradation (%) at 6 Months |
|---|---|
| Glycerol | <5 |
| Thiamine HCl | 8 ± 2 |
Q. Methodological Notes
- Statistical Rigor: Use SAS or R for ANOVA/regression models, ensuring pen-level replication in animal studies .
- Ethical Compliance: Follow IACUC guidelines for animal welfare and EMA protocols for clinical trials .
- Data Contradictions: Address discrepancies (e.g., neurotoxicity thresholds) via meta-analysis or dose-escalation studies .
Propiedades
IUPAC Name |
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
LXNHXLLTXMVWPM-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=NC=C(C(=C1O)CO)CO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C8H11NO3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
58-56-0 (hydrochloride) |
Source
|
| Record name | Pyridoxine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000065236 | |
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DSSTOX Substance ID |
DTXSID4023541 |
Source
|
| Record name | Pyridoxine | |
| Source | EPA DSSTox | |
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| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
169.18 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
White powder; [Alfa Aesar MSDS], Solid |
Source
|
| Record name | Pyridoxine | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
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| Record name | Pyridoxine | |
| Source | Human Metabolome Database (HMDB) | |
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Solubility |
79 mg/mL |
Source
|
| Record name | Pyridoxine | |
| Source | DrugBank | |
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| Record name | Pyridoxine | |
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Vapor Pressure |
0.00000028 [mmHg] |
Source
|
| Record name | Pyridoxine | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
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Mechanism of Action |
Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA). |
Source
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| Record name | Pyridoxine | |
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CAS No. |
65-23-6 |
Source
|
| Record name | Pyridoxine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=65-23-6 | |
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| Record name | Pyridoxine [INN:BAN] | |
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| Record name | Pyridoxine | |
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| Record name | pyridoxine | |
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| Record name | 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- | |
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| Record name | Pyridoxine | |
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| Record name | Pyridoxine | |
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| Record name | PYRIDOXINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
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| Record name | Pyridoxine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000239 | |
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Melting Point |
159-162 °C, 159 - 162 °C |
Source
|
| Record name | Pyridoxine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00165 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Pyridoxine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000239 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Synthesis routes and methods I
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Synthesis routes and methods II
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Retrosynthesis Analysis
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Feasible Synthetic Routes
Descargo de responsabilidad e información sobre productos de investigación in vitro
Tenga en cuenta que todos los artículos e información de productos presentados en BenchChem están destinados únicamente con fines informativos. Los productos disponibles para la compra en BenchChem están diseñados específicamente para estudios in vitro, que se realizan fuera de organismos vivos. Los estudios in vitro, derivados del término latino "in vidrio", involucran experimentos realizados en entornos de laboratorio controlados utilizando células o tejidos. Es importante tener en cuenta que estos productos no se clasifican como medicamentos y no han recibido la aprobación de la FDA para la prevención, tratamiento o cura de ninguna condición médica, dolencia o enfermedad. Debemos enfatizar que cualquier forma de introducción corporal de estos productos en humanos o animales está estrictamente prohibida por ley. Es esencial adherirse a estas pautas para garantizar el cumplimiento de los estándares legales y éticos en la investigación y experimentación.
