Chlorpropamid
Übersicht
Beschreibung
Chlorpropamid ist ein Antidiabetikum, das zur Klasse der Sulfonylharnstoffe gehört. Es wird hauptsächlich zur Behandlung von Typ-2-Diabetes mellitus eingesetzt, indem es die Freisetzung von Insulin aus den Betazellen der Bauchspeicheldrüse stimuliert. This compound ist ein lang wirkendes Sulfonylharnstoff der ersten Generation und bekannt für seine Fähigkeit, den Blutzuckerspiegel über einen längeren Zeitraum zu halten .
Wirkmechanismus
Target of Action
Chlorpropamide, an oral antihyperglycemic agent, primarily targets the β cells of the pancreas . These cells play a crucial role in the regulation of blood glucose levels by secreting insulin, a hormone that promotes the uptake and storage of glucose .
Mode of Action
Chlorpropamide belongs to the sulfonylurea class of insulin secretagogues . It acts by binding to ATP-sensitive potassium channels on the pancreatic cell surface . This binding reduces potassium conductance, causing depolarization of the membrane . The resulting depolarization stimulates the β cells of the pancreas to release insulin .
Biochemical Pathways
The action of chlorpropamide affects several biochemical pathways. By stimulating insulin secretion, it increases both basal insulin secretion and meal-stimulated insulin release . Additionally, it enhances peripheral glucose utilization, decreases hepatic gluconeogenesis, and may increase the number and sensitivity of insulin receptors .
Pharmacokinetics
Chlorpropamide exhibits favorable ADME (Absorption, Distribution, Metabolism, and Excretion) properties. It is readily absorbed from the gastrointestinal tract, with a bioavailability of over 90% . The drug reaches maximal plasma concentrations 3 to 5 hours after administration . It has a long plasma half-life of 36 hours, making it effective for about 24 hours . Chlorpropamide is largely bound to plasma proteins, and more than 99% of it is excreted unchanged via the kidneys .
Result of Action
The primary result of chlorpropamide’s action is the reduction of blood glucose levels. By stimulating the release of insulin, it promotes the uptake and storage of glucose, thereby lowering blood glucose levels . It can cause relatively long episodes of hypoglycemia, which is why consistent food intake is required to decrease this risk .
Action Environment
The action, efficacy, and stability of chlorpropamide can be influenced by various environmental factors. For instance, the risk of hypoglycemia is increased in elderly, debilitated, and malnourished individuals . Renal and hepatic dysfunction may also increase the risk of hypoglycemia .
Wissenschaftliche Forschungsanwendungen
Chlorpropamid hat verschiedene Anwendungen in der wissenschaftlichen Forschung, darunter:
Chemie: Wird als Modellverbindung zur Untersuchung der Chemie und Reaktionen von Sulfonylharnstoffen verwendet.
Biologie: Untersucht auf seine Auswirkungen auf die Insulinsekretion und die Funktion der Betazellen der Bauchspeicheldrüse.
Medizin: Untersucht auf seine therapeutischen Wirkungen bei der Behandlung von Typ-2-Diabetes und seine möglichen Nebenwirkungen.
Industrie: Wird bei der Entwicklung neuer Antidiabetika und Formulierungen verwendet
Wirkmechanismus
This compound übt seine Wirkungen aus, indem es an ATP-sensitive Kaliumkanäle auf der Oberfläche der Betazellen der Bauchspeicheldrüse bindet. Diese Bindung reduziert die Kaliumleitfähigkeit, was zu einer Depolarisation der Zellmembran führt. Die Depolarisation löst die Öffnung spannungsgesteuerter Kalziumkanäle aus, was zu einem Einstrom von Kalziumionen führt. Die erhöhte intrazelluläre Kalziumkonzentration stimuliert die Exozytose von Insulin-haltigen Granula, wodurch die Insulinsekretion erhöht wird .
Biochemische Analyse
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
Vorbereitungsmethoden
Synthesewege und Reaktionsbedingungen
Chlorpropamid kann durch einen mehrstufigen Prozess synthetisiert werden, der die Reaktion von 4-Chlorbenzolsulfonylchlorid mit Propylamin zur Bildung von 4-Chlorbenzolsulfonamid umfasst. Dieses Zwischenprodukt wird dann mit Phosgen und Ammoniak umgesetzt, um this compound zu erhalten. Die Reaktionsbedingungen umfassen typischerweise kontrollierte Temperaturen und die Verwendung von Lösungsmitteln wie Dichlormethan .
Industrielle Produktionsverfahren
Die industrielle Produktion von this compound folgt ähnlichen Synthesewegen, jedoch in größerem Maßstab. Das Verfahren umfasst die Verwendung großer Reaktoren und die präzise Kontrolle der Reaktionsbedingungen, um eine hohe Ausbeute und Reinheit zu gewährleisten. Das Endprodukt wird strengen Qualitätskontrollen unterzogen, um pharmazeutische Standards zu erfüllen .
Analyse Chemischer Reaktionen
Arten von Reaktionen
Chlorpropamid unterliegt verschiedenen Arten von chemischen Reaktionen, darunter:
Oxidation: this compound kann zu Sulfoxiden und Sulfonen oxidiert werden.
Reduktion: Reduktionsreaktionen können this compound in seine entsprechenden Amin-Derivate umwandeln.
Substitution: This compound kann nukleophile Substitutionsreaktionen eingehen, insbesondere an der Sulfonylgruppe
Häufige Reagenzien und Bedingungen
Oxidation: Häufige Oxidationsmittel sind Wasserstoffperoxid und Kaliumpermanganat.
Reduktion: Als Reduktionsmittel werden Lithiumaluminiumhydrid und Natriumborhydrid verwendet.
Substitution: Nukleophile wie Amine und Thiole können unter milden Bedingungen mit this compound reagieren
Hauptprodukte, die gebildet werden
Oxidation: Sulfoxide und Sulfone.
Reduktion: Aminderivate.
Substitution: Verschiedene substituierte Sulfonamide
Vergleich Mit ähnlichen Verbindungen
Chlorpropamid wird mit anderen Sulfonylharnstoffen verglichen, wie z. B.:
- Gliclazid
- Tolbutamid
- Glipizid
Einzigartigkeit
This compound ist einzigartig durch seine lange Wirkdauer und seine Fähigkeit, über einen längeren Zeitraum stabile Blutzuckerspiegel zu halten. Es birgt ein höheres Risiko, Hypoglykämie zu verursachen als kürzer wirkende Sulfonylharnstoffe wie Gliclazid und Tolbutamid .
Ähnliche Verbindungen
- Gliclazid : Kürzer wirkendes Sulfonylharnstoff mit einem geringeren Risiko für Hypoglykämie.
- Tolbutamid : Ein weiteres Sulfonylharnstoff der ersten Generation mit einer kürzeren Wirkdauer.
- Glipizid : Sulfonylharnstoff der zweiten Generation mit einem günstigeren Nebenwirkungsprofil .
Eigenschaften
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 | |
| 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 | Chlorpropamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014810 | |
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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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| Record name | Chlorpropamide | |
| Source | Human Metabolome Database (HMDB) | |
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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 | |
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| URL | https://www.drugbank.ca/drugs/DB00672 | |
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| Record name | CHLORPROPAMIDE | |
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Color/Form |
Crystals from dil ethanol, WHITE, CRYSTALLINE POWDER, White, crystalline powder | |
CAS No. |
94-20-2 |
Source
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| Record name | CHLOROPROPAMIDE | |
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| Record name | Chlorpropamide [USP:INN:BAN:JAN] | |
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Melting Point |
261 to 264 °F (NTP, 1992), 129.2-129.8, 127-129 °C, 127 - 129 °C |
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| Record name | CHLOROPROPAMIDE | |
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