氯磺丙脲
货号:
B1668849
CAS 编号:
94-20-2
分子量:
276.74 g/mol
InChI 键:
RKWGIWYCVPQPMF-UHFFFAOYSA-N
注意:
仅供研究使用。不适用于人类或兽医用途。
概述
描述
氯磺丙脲是一种抗糖尿病药物，属于磺酰脲类有机化合物。它主要用于治疗2型糖尿病，通过刺激胰腺β细胞释放胰岛素来发挥作用。 氯磺丙脲是一种长效的第一代磺酰脲类药物，以其能够在较长时期内维持血糖水平而闻名 .
作用机制
氯磺丙脲通过与胰腺β细胞表面上的ATP敏感性钾通道结合来发挥作用。这种结合降低了钾传导，导致细胞膜去极化。去极化触发电压依赖性钙通道的开放，导致钙离子流入。 胞内钙浓度升高刺激含有胰岛素的颗粒的胞吐作用，从而增加胰岛素分泌 .
科学研究应用
氯磺丙脲有几种科学研究应用，包括：
化学： 用作模型化合物研究磺酰脲化学和反应。
生物学： 研究其对胰岛素分泌和胰腺β细胞功能的影响。
医学： 研究其在控制2型糖尿病中的治疗作用及其潜在的副作用。
工业： 用于开发新的抗糖尿病药物和制剂
生化分析
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
准备方法
合成路线和反应条件
氯磺丙脲可以通过多步合成过程合成，涉及4-氯苯磺酰氯与丙胺反应生成4-氯苯磺酰胺。然后将该中间体与光气和氨反应生成氯磺丙脲。 反应条件通常包括受控温度和使用诸如二氯甲烷之类的溶剂 .
工业生产方法
氯磺丙脲的工业生产遵循类似的合成路线，但规模更大。该过程涉及使用大型反应器和精确控制反应条件，以确保高产率和纯度。 最终产品经过严格的质量控制措施，以符合药物标准 .
化学反应分析
反应类型
氯磺丙脲会经历几种类型的化学反应，包括：
氧化： 氯磺丙脲可以被氧化生成亚砜和砜。
还原： 还原反应可以将氯磺丙脲转化为其相应的胺衍生物。
常用试剂和条件
氧化： 常见的氧化剂包括过氧化氢和高锰酸钾。
还原： 使用诸如氢化锂铝和硼氢化钠之类的还原剂。
主要产物
氧化： 亚砜和砜。
还原： 胺衍生物。
取代： 各种取代的磺酰胺
相似化合物的比较
氯磺丙脲与其他磺酰脲类药物比较，例如：
- 格列齐特
- 甲苯磺丁脲
- 格列本脲
独特性
氯磺丙脲的独特性在于其作用时间长，能够在较长时期内维持稳定的血糖水平。 与格列齐特和甲苯磺丁脲等作用时间较短的磺酰脲类药物相比，它有更高的导致低血糖的风险 .
类似化合物
- 格列齐特： 作用时间较短的磺酰脲类药物，低血糖风险较低。
- 甲苯磺丁脲： 另一种作用时间较短的第一代磺酰脲类药物。
- 格列本脲： 第二代磺酰脲类药物，具有更良好的副作用概况 .
属性
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 | |
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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 | |
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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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Synthesis routes and methods
Procedure details
n-Propylamine (5.9 g., 0.1 mole.) and propylene carbonate (10.2 g., 0.1 mole.) were mixed and heated at 60° over night. To the resulting hydroxypropyl-n-propylcarbomate were added p-chlorobenzene sulfonamide (10.67 g., as sodium salt) and DMF (200 ml.) and the mixture was heated at 120° for 4 hours. After evaporation of the solvent the residue was taken up in water (200 ml.) and the solution adjusted to pH 8 by the addition of acetic acid. Unreacted p-chlorobenzene sulfonamide (2 g.) separated out and was collected. Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose infrared spectrum was identical with that of an authentic sample.
[Compound]
Name
hydroxypropyl-n-propylcarbomate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Retrosynthesis Analysis
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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
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Chlorpropamide
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Chlorpropamide
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Chlorpropamide
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Reactant of Route 5
Chlorpropamide
Reactant of Route 6
Reactant of Route 6
Chlorpropamide
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