Nifedipine
Número de catálogo:
B1678770
Número CAS:
21829-25-4
Peso molecular:
346.3 g/mol
Clave InChI:
HYIMSNHJOBLJNT-UHFFFAOYSA-N
Atención:
Solo para uso de investigación. No para uso humano o veterinario.
Descripción general
Descripción
El nifedipino es un bloqueador de los canales de calcio de dihidropiridina utilizado principalmente para tratar la angina de pecho, la hipertensión, el fenómeno de Raynaud y el parto prematuro . Fue desarrollado por primera vez por Bayer y descrito en la literatura en 1972 . El nifedipino funciona inhibiendo el flujo de iones de calcio hacia el músculo cardíaco y las células del músculo liso, lo que provoca vasodilatación y reducción de la presión arterial .
Mecanismo De Acción
El nifedipino ejerce sus efectos bloqueando los canales de calcio de tipo L en las células del músculo liso vascular y del músculo cardíaco . Esta inhibición evita la entrada de iones de calcio, lo que provoca la relajación de las células del músculo liso, la vasodilatación y una posterior disminución de la presión arterial . El objetivo molecular principal del nifedipino es el canal de calcio de tipo L .
Análisis Bioquímico
Biochemical Properties
Nifedipine’s primary role in biochemical reactions is as an inhibitor of L-type calcium channels . By blocking these channels, this compound prevents the influx of calcium ions into cells, which is a crucial step in muscle contraction and neurotransmitter release .
Cellular Effects
This compound has a profound effect on various types of cells, particularly those in the heart and blood vessels . By inhibiting calcium influx, this compound reduces the contractility of cardiac and smooth muscle cells, leading to a decrease in blood pressure . It also influences cell signaling pathways related to calcium homeostasis and can affect gene expression related to these pathways .
Molecular Mechanism
This compound exerts its effects at the molecular level primarily through its interaction with L-type calcium channels . It binds to the alpha-1 subunit of these channels, causing a conformational change that prevents the passage of calcium ions . This inhibition can lead to downstream effects on gene expression and cellular metabolism .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound can be observed to change over time. It is almost completely absorbed in the gastrointestinal tract but has a bioavailability of 45-68%, partly due to first-pass metabolism . Over time, the drug is metabolized and excreted, and its effects diminish .
Dosage Effects in Animal Models
The effects of this compound in animal models have been shown to vary with dosage . At lower doses, this compound effectively reduces blood pressure without significant adverse effects. At higher doses, it can cause hypotension and reflex tachycardia .
Metabolic Pathways
This compound is metabolized primarily in the liver by the cytochrome P450 system . It undergoes extensive first-pass metabolism, leading to the formation of several metabolites .
Transport and Distribution
After absorption, this compound is distributed throughout the body. It is highly lipophilic, allowing it to cross cell membranes easily . It is also highly protein-bound in plasma, which can affect its distribution .
Subcellular Localization
As a lipophilic compound, this compound can diffuse across cell membranes and reach various subcellular compartments . Its primary site of action, the L-type calcium channels, are located in the cell membrane . It can also affect intracellular calcium stores and other subcellular structures .
Métodos De Preparación
Rutas de síntesis y condiciones de reacción: El nifedipino se puede sintetizar mediante la reacción de Hantzsch, que implica la condensación de un aldehído, un β-ceto éster y amoníaco . Por ejemplo, el acetoacetato de metilo y el orto-nitrobenzaldehído se hacen reaccionar en presencia de amoníaco para formar nifedipino .
Métodos de producción industrial: En entornos industriales, el nifedipino se prepara a menudo como una dispersión sólida utilizando polímeros solubles en agua como la polivinilpirrolidona para mejorar su biodisponibilidad . Otro método implica la preparación de nanopartículas poliméricas cargadas con nifedipino utilizando técnicas como la nanoprecipitación y la evaporación de emulsiones-disolventes .
Análisis De Reacciones Químicas
Tipos de reacciones: El nifedipino sufre varias reacciones químicas, incluida la reducción, la oxidación y la sustitución. Por ejemplo, puede reducirse utilizando un sistema de zinc y ácido clorhídrico .
Reactivos y condiciones comunes:
Productos principales:
Aplicaciones Científicas De Investigación
El nifedipino tiene una amplia gama de aplicaciones de investigación científica:
Comparación Con Compuestos Similares
El nifedipino se compara a menudo con otros bloqueadores de los canales de calcio como la amlodipina, la nicardipina y la felodipina . Si bien todos estos compuestos comparten un mecanismo de acción similar, el nifedipino es único debido a su rápida aparición de acción y su vida media más corta . Esto lo hace particularmente útil para controlar emergencias hipertensivas agudas .
Compuestos similares:
- Amlodipina
- Nicardipina
- Felodipina
- Isradipina
- Nimodipina
- Nitrendipina
- Lacidipina
El perfil farmacocinético distintivo del nifedipino y su eficacia en el tratamiento de una variedad de afecciones cardiovasculares resaltan su importancia en la terapia médica.
Propiedades
IUPAC Name |
dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HYIMSNHJOBLJNT-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C17H18N2O6 |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | nifedipine | |
| Source | Wikipedia | |
| URL | https://en.wikipedia.org/wiki/Nifedipine | |
| Description | Chemical information link to Wikipedia. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
60299-11-8 (mono-hydrochloride) |
Source
|
| Record name | Nifedipine [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0021829254 | |
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DSSTOX Substance ID |
DTXSID2025715 |
Source
|
| Record name | Nifedipine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2025715 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
346.3 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Nifedipine appears as odorless yellow crystals or powder. Tasteless. (NTP, 1992), Solid |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| 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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| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015247 | |
| 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. | |
Solubility |
less than 1 mg/mL at 67.1 °F (NTP, 1992), Insoluble, Solubility at 20 °C (g/L): acetone 250, methylene chloride 160, chloroform 140, ethyl acetate 50, methanol 26, ethanol 17, In water, 1.7X10-5 mol/L = 5.9 mg/L at 25 °C, 1.77e-02 g/L |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| 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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| Record name | Nifedipine | |
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| Record name | Nifedipine | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
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| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015247 | |
| 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. | |
Vapor Pressure |
2.6X10-8 mm Hg at 25 °C |
Source
|
| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Mechanism of Action |
Nifedipine blocks voltage gated L-type calcium channels in vascular smooth muscle and myocardial cells. This blockage prevents the entry of calcium ions into cells during depolarization, reducing peripheral arterial vascular resistance and dilating coronary arteries. These actions reduce blood pressure and increase the supply of oxygen to the heart, alleviating angina., The principal physiologic action of nifedipine is to inhibit the transmembrane influx of extracellular calcium ions across the membranes of myocardial cells and vascular smooth muscle cells, without changing serum calcium concentrations. Calcium plays important roles in the excitation-contraction coupling processes of the heart and vascular smooth muscle cells and in the electrical discharge of the specialized conduction cells of the heart. The membranes of these cells contain numerous channels that carry a slow inward current and that are selective for calcium. Activation of these slow calcium channels contributes to the plateau phase (phase 2) of the action potential of cardiac and vascular smooth muscle cells. The exact mechanism whereby nifedipine inhibits calcium ion influx across the slow calcium channels is not known, but the drug is thought to inhibit ion-control gating mechanisms of the channel, deform the slow channel, and/or interfere with release of calcium from the sarcoplasmic reticulum. By inhibiting calcium influx, nifedipine inhibits the contractile processes of cardiac and vascular smooth muscle, thereby dilating the main coronary and systemic arteries., Nifedipine is a peripheral arterial vasodilator which acts directly on vascular smooth muscle. The binding of nifedipine to voltage-dependent and possibly receptor-operated channels in vascular smooth muscle results in an inhibition of calcium influx through these channels. Stores of intracellular calcium in vascular smooth muscle are limited and thus dependent upon the influx of extracellular calcium for contraction to occur. The reduction in calcium influx by nifedipine causes arterial vasodilation and decreased peripheral vascular resistance which results in reduced arterial blood pressure. |
Source
|
| Record name | Nifedipine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01115 | |
| 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. | |
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| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Impurities |
Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate, Dimethyl 2,6-dimethyl-4-(2_nitrosophenyl)pyridine-3,5-dicarboxylate, Methyl 2-(2-nitrobenzylidene)-3-oxobutanoate, Methyl 3-aminobut-2-enoate |
Source
|
| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Yellow crystals | |
CAS No. |
21829-25-4, 193689-82-6, 915092-63-6 |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| 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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| Record name | 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, radical ion(1-) | |
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| Record name | Nifedipine | |
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| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | NIFEDIPINE | |
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Melting Point |
342 to 345 °F (NTP, 1992), 172-174 °C, 172 - 174 °C |
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|
| Record name | NIFEDIPINE | |
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Synthesis routes and methods I
Procedure details
2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.2 mole, 23.2 g) and NH4OH (12 ml) were heated in methanol (20 ml) in the presence of pyridine for several (7) hours. After cooling to 15° C. the precipitated product was filtered off. The crude product was crystallized from acetic acid to yield 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (21.7 g, 62% of the theory), m.p. 172°-174° C.
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Reaction Step One
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Synthesis routes and methods II
Procedure details
2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.21 mole, 26 g), NH4OH (12 ml) and methanol (45 ml) were heated under reflux for 5 hours. After cooling to 15° C. the precipitated product was filtered off. The crystallization of the crude product from acetic acid yielded 4-(2'-nitrophenyl)-2,6 dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (19.0 g, 55% of the theory), m.p. 173°-174° C.
Name
2-Nitrobenzaldehyde diacetate
Quantity
25.4 g
Type
reactant
Reaction Step One
Synthesis routes and methods III
Procedure details
One proceeds as described in Example 7 except that 0.4 mole of 2-nitro-benzaldehyde, 0.415 mole of a 25% aqueous ammonium hydroxide solution and 1.40 moles of methyl acetoacetate are used. Thus 112.1 g of nifedipine are obtained, yield 81%, m.p.: 172°-175° C. The product complies with the requirements of USP XXI without further purification.
Name
Yield
81%
Synthesis routes and methods IV
Procedure details
Into a 1-liter glass reactor 60.4 g (0.4 mole) of 2-nitro-benzaldehyde, 102.1 g (0.88 mole) of methyl acetoacetate, 28.25 g (0.415 mole) of a 25% aqueous ammonium hydroxide solution and 150 ml of methanol are weighed in. The reactor is closed, whereupon the reaction mixture is heated to boiling at a temperature of 101°-103° C. and a pressure of 2.0-2.2 bar for 5 hours. The reaction mixture is cooled to 0°-5° C., the precipitated product is filtered and washed with methanol. Thus 110.5 g of nifedipine are obtained, yield 79.8%, m.p.: 171.5°-175° C.
Synthesis routes and methods V
Procedure details
Nifedipine-isothiocyanate was also coupled to casein, ovalbumin and keyhole limpet hemocyanin using the procedures described above. An alternate procedure for the coupling of nifedipine-isothiocyanate to various proteins (i.e., bovine serum albumin, ovalbumin, casein and keyhole limpet hemocyanin) was to dissolve the protein (20 mg) in 2 ml of 100 mM sodium bicarbonate (pH 9.0) and then incubate with 0.8 mg of nifedipine-isothiocyanate (dissolved in ethanol to make the final concentration of ethanol in the incubation medium 38 percent) for 24 hours at 37° C. with shaking in the dark. This alternate procedure is useful for producing nifedipine conjugates at high protein concentrations.
Name
Nifedipine isothiocyanate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
nifedipine isothiocyanate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
nifedipine isothiocyanate
Quantity
0.8 mg
Type
reactant
Reaction Step Three
Name
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
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| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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