Clorpropamida
Descripción general
Descripción
La clorpropamida es un fármaco antidiabético que pertenece a la clase de compuestos orgánicos de las sulfonilureas. Se utiliza principalmente para tratar la diabetes mellitus tipo 2 mediante la estimulación de la liberación de insulina de las células beta pancreáticas. La this compound es una sulfonilurea de primera generación de acción prolongada y es conocida por su capacidad para mantener los niveles de glucosa en sangre durante un período prolongado .
Mecanismo De Acción
La clorpropamida ejerce sus efectos uniéndose a los canales de potasio sensibles al ATP en la superficie de la célula beta pancreática. Esta unión reduce la conductancia del potasio, lo que provoca la despolarización de la membrana celular. La despolarización desencadena la apertura de los canales de calcio activados por voltaje, lo que conduce a una afluencia de iones calcio. El aumento de la concentración intracelular de calcio estimula la exocitosis de los gránulos que contienen insulina, lo que aumenta la secreción de insulina .
Aplicaciones Científicas De Investigación
La clorpropamida tiene varias aplicaciones de investigación científica, que incluyen:
Química: Se utiliza como compuesto modelo para estudiar la química y las reacciones de las sulfonilureas.
Biología: Se investiga por sus efectos sobre la secreción de insulina y la función de las células beta pancreáticas.
Medicina: Se estudia por sus efectos terapéuticos en el manejo de la diabetes tipo 2 y sus posibles efectos secundarios.
Industria: Se utiliza en el desarrollo de nuevos fármacos y formulaciones antidiabéticos
Análisis Bioquímico
Biochemical Properties
Chlorpropamide functions by stimulating the β cells of the pancreas to release insulin . This action increases both basal insulin secretion and meal-stimulated insulin release . Chlorpropamide also enhances peripheral glucose utilization, decreases hepatic gluconeogenesis, and may increase the number and sensitivity of insulin receptors .
Cellular Effects
Chlorpropamide exerts its effects on various types of cells, primarily the pancreatic beta cells . It stimulates these cells to release insulin, thereby influencing cell function . This impact on cell signaling pathways leads to increased insulin secretion and enhanced glucose utilization .
Molecular Mechanism
The molecular mechanism of action of Chlorpropamide involves its binding to ATP-sensitive potassium channels on the pancreatic cell surface . This binding reduces potassium conductance and causes depolarization of the membrane . This depolarization triggers the release of insulin from the pancreatic beta cells .
Temporal Effects in Laboratory Settings
Chlorpropamide exhibits a long half-life of 36 hours, making it effective for about 24 hours, longer than other sulfonylureas . A stable plasma level is only reached after three days of continuous application . More than 99% of Chlorpropamide is excreted unchanged via the kidneys .
Dosage Effects in Animal Models
In animal models, the anti-aging effects of Chlorpropamide have been observed at a dosage of 10 mg/kg, which is much lower than the 200 mg/kg dosage used for its hypoglycemic effect . Chlorpropamide administration at this dosage had no significant effect on the blood glucose level of non-diabetic mice .
Metabolic Pathways
Chlorpropamide is extensively metabolized in the liver, likely through the CYP2C9 enzyme . Up to 80% of the dose is metabolized, forming metabolites . The metabolites and unchanged drug are excreted in the urine .
Transport and Distribution
Chlorpropamide is absorbed rapidly after oral administration . It is distributed within the body with a volume of distribution ranging from 0.13 to 0.23 L/kg . It is bound to plasma proteins at a rate of 90% .
Subcellular Localization
The subcellular localization of Chlorpropamide is primarily within the pancreatic beta cells, where it exerts its insulin-secreting effects
Métodos De Preparación
Rutas sintéticas y condiciones de reacción
La clorpropamida se puede sintetizar mediante un proceso de varios pasos que implica la reacción de cloruro de 4-clorobencenosulfonilo con propilamina para formar 4-clorobencenosulfonamida. Este intermedio se hace reaccionar luego con fosgeno y amoníaco para producir this compound. Las condiciones de reacción suelen implicar temperaturas controladas y el uso de disolventes como el diclorometano .
Métodos de producción industrial
La producción industrial de this compound sigue rutas sintéticas similares pero a mayor escala. El proceso implica el uso de reactores grandes y un control preciso de las condiciones de reacción para garantizar un alto rendimiento y pureza. El producto final se somete a rigurosas medidas de control de calidad para cumplir con los estándares farmacéuticos .
Análisis De Reacciones Químicas
Tipos de reacciones
La clorpropamida experimenta varios tipos de reacciones químicas, que incluyen:
Oxidación: La this compound se puede oxidar para formar sulfoxidos y sulfonas.
Reducción: Las reacciones de reducción pueden convertir la this compound en sus derivados de amina correspondientes.
Sustitución: La this compound puede sufrir reacciones de sustitución nucleofílica, particularmente en el grupo sulfonilo
Reactivos y condiciones comunes
Oxidación: Los agentes oxidantes comunes incluyen peróxido de hidrógeno y permanganato de potasio.
Reducción: Se utilizan agentes reductores como hidruro de aluminio y litio y borohidruro de sodio.
Sustitución: Los nucleófilos como las aminas y los tioles pueden reaccionar con la this compound en condiciones suaves
Principales productos formados
Oxidación: Sulfoxidos y sulfonas.
Reducción: Derivados de amina.
Sustitución: Varias sulfonamidas sustituidas
Comparación Con Compuestos Similares
La clorpropamida se compara con otras sulfonilureas como:
- Gliclazida
- Tolbutamida
- Glipizida
Unicidad
La this compound es única debido a su larga duración de acción y su capacidad para mantener los niveles de glucosa en sangre estables durante un período prolongado. Tiene un mayor riesgo de causar hipoglucemia en comparación con las sulfonilureas de acción más corta como la gliclazida y la tolbutamida .
Compuestos similares
- Gliclazida : Sulfonilurea de acción más corta con un menor riesgo de hipoglucemia.
- Tolbutamida : Otra sulfonilurea de primera generación con una duración de acción más corta.
- Glipizida : Sulfonilurea de segunda generación con un perfil de efectos secundarios más favorable .
Propiedades
IUPAC Name |
1-(4-chlorophenyl)sulfonyl-3-propylurea |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
RKWGIWYCVPQPMF-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H13ClN2O3S |
Source
|
| Record name | CHLOROPROPAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20013 | |
| 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 | |
DSSTOX Substance ID |
DTXSID9020322 |
Source
|
| Record name | Chlorpropamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9020322 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
276.74 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Chloropropamide is a white crystalline powder with a slight odor. (NTP, 1992), Solid |
Source
|
| Record name | CHLOROPROPAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20013 | |
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| Record name | Chlorpropamide | |
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Solubility |
>41.5 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 57 °F (NTP, 1992), 2.2 mg/ml in water @ pH 6; practically insol in water @ pH 7.3; sol in alcohol; moderately sol in chloroform; sparingly sol in ether, benzene, In water, 258 mg/l @ 37 °C, 1.57e-01 g/L |
Source
|
| Record name | SID855559 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | CHLOROPROPAMIDE | |
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| Record name | Chlorpropamide | |
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Mechanism of Action |
Sulfonylureas such as chlorpropamide bind to ATP-sensitive potassium channels on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin., ...ACTION OF SULFONYLUREAS APPEARS TO BE STIMULATION OF RELEASE OF INSULIN FROM BETA CELLS. ...TO BE EFFECTIVE, PT MUST HAVE SOME FUNCTIONAL ISLET CELLS... /HYPOGLYCEMIC SULFONYLUREAS/, Sulfonylureas cause hypoglycemia by stimulating insulin release from pancreatic beta cells. Their effects in the treatment of diabetes ... are more complex. /Sulfonylureas/, Sulfonylureas are now...thought to act by a number of different mechanisms. 1. ...produce a depolarization of the pancreatic islet beta cell membrane potassium ion permeability. This results in a release of preformed insulin into the circulation and occurs mostly in non-insulin dependent diabetics. 2. ...reduce basal glucose output from the liver... 3. increase insulin receptor binding... 4. ...increasing intracellular levels of AMP... 5. increase insulin secretion by suppressing the release of glucagon and somatostatin from alpha and delta pancreatic cells. /Sulfonylureas/, Sulfonylureas lower blood glucose in NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor on the beta cell. Sulfonylureas inhibit the ATP potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin containing granules by exocytosis, an effect similar to that of glucose. Insulin is a hormone that lowers blood glucose and controls the storage and metabolism of carbohydrates, proteins, and fats. Therefore, sulfonylureas are effective only in patients whose pancreata are capable of producing insulin. /Sulfonylurea antidiabetic agents/ |
Source
|
| Record name | Chlorpropamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00672 | |
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| Record name | CHLORPROPAMIDE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2051 | |
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Color/Form |
Crystals from dil ethanol, WHITE, CRYSTALLINE POWDER, White, crystalline powder | |
CAS No. |
94-20-2 |
Source
|
| Record name | CHLOROPROPAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20013 | |
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Melting Point |
261 to 264 °F (NTP, 1992), 129.2-129.8, 127-129 °C, 127 - 129 °C |
Source
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| Record name | CHLOROPROPAMIDE | |
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Synthesis routes and methods
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Retrosynthesis Analysis
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| 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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