Chlorpropamide
カタログ番号:
B1668849
CAS番号:
94-20-2
分子量:
276.74 g/mol
InChIキー:
RKWGIWYCVPQPMF-UHFFFAOYSA-N
注意:
研究専用です。人間または獣医用ではありません。
概要
説明
クロルプロパミドは、スルホニル尿素系有機化合物に属する抗糖尿病薬です。主に膵臓のβ細胞からのインスリン分泌を刺激することで、2型糖尿病の治療に使用されます。 クロルプロパミドは、長時間の作用を持つ第一世代のスルホニル尿素であり、長期間にわたって血糖値を維持できることで知られています .
作用機序
クロルプロパミドは、膵臓β細胞表面のATP感受性カリウムチャネルに結合することで効果を発揮します。この結合はカリウムコンダクタンスを低下させ、細胞膜の脱分極を引き起こします。脱分極は電位依存性カルシウムチャネルの開口を引き起こし、カルシウムイオンの流入につながります。 細胞内カルシウム濃度の上昇は、インスリン含有顆粒のエクソサイトーシスを刺激し、インスリン分泌を増加させます .
生化学分析
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 . This compound also enhances peripheral glucose utilization, decreases hepatic gluconeogenesis, and may increase the number and sensitivity of insulin receptors .
Cellular Effects
This compound 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 this compound 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
This compound 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 this compound is excreted unchanged via the kidneys .
Dosage Effects in Animal Models
In animal models, the anti-aging effects of this compound 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 . This compound administration at this dosage had no significant effect on the blood glucose level of non-diabetic mice .
Metabolic Pathways
This compound 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
This compound 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 this compound is primarily within the pancreatic beta cells, where it exerts its insulin-secreting effects
準備方法
合成経路と反応条件
クロルプロパミドは、4-クロロベンゼンスルホニルクロリドとプロピルアミンを反応させて4-クロロベンゼンスルホンアミドを生成する多段階プロセスによって合成することができます。この中間体をホスゲンとアンモニアと反応させてクロルプロパミドが得られます。 反応条件は通常、制御された温度とジクロロメタンなどの溶媒の使用を伴います .
工業生産方法
クロルプロパミドの工業生産は、同様の合成経路に従いますが、より大規模に行われます。このプロセスでは、大型反応器を使用し、反応条件を厳密に管理することで、高収率で高純度の製品が得られます。 最終製品は、医薬品規格に適合するように厳格な品質管理検査を受けます .
化学反応の分析
反応の種類
クロルプロパミドは、以下の化学反応をいくつか起こします。
酸化: クロルプロパミドは、酸化されてスルホキシドやスルホンを生成することができます。
還元: 還元反応は、クロルプロパミドを対応するアミン誘導体に変化させることができます。
一般的な試薬と条件
酸化: 一般的な酸化剤には、過酸化水素と過マンガン酸カリウムが含まれます。
還元: 水素化リチウムアルミニウムや水素化ホウ素ナトリウムなどの還元剤が使用されます。
生成される主な生成物
酸化: スルホキシドやスルホン。
還元: アミン誘導体。
置換: さまざまな置換スルホンアミド
科学研究への応用
クロルプロパミドは、以下の科学研究に応用されています。
化学: スルホニル尿素の化学と反応を研究するためのモデル化合物として使用されます。
生物学: インスリン分泌と膵臓β細胞の機能への影響について研究されています。
医学: 2型糖尿病の管理における治療効果と潜在的な副作用について研究されています。
科学的研究の応用
Chlorpropamide has several scientific research applications, including:
Chemistry: Used as a model compound to study sulfonylurea chemistry and reactions.
Biology: Investigated for its effects on insulin secretion and pancreatic beta-cell function.
Medicine: Studied for its therapeutic effects in managing type 2 diabetes and its potential side effects.
Industry: Used in the development of new antidiabetic drugs and formulations
類似化合物との比較
クロルプロパミドは、以下のスルホニル尿素系薬剤と比較されます。
- グリクラジド
- トルブタミド
- グリピジド
独自性
クロルプロパミドは、長時間の作用時間と、長期間にわたって安定した血糖値を維持できるという点で独特です。 グリクラジドやトルブタミドなどの短時間作用型のスルホニル尿素系薬剤と比較して、低血糖を起こすリスクが高い .
類似化合物
- グリクラジド : 低血糖のリスクが低い、短時間作用型のスルホニル尿素系薬剤です。
- トルブタミド : 短時間作用型の第一世代スルホニル尿素系薬剤です。
- グリピジド : 副作用のプロファイルがより良好な第二世代スルホニル尿素系薬剤です .
特性
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. | |
| 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. | |
| 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 | |
| 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 |
>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 | |
| Source | CAMEO Chemicals | |
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| 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 | 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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| Record name | Chlorpropamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014810 | |
| 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. | |
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 | |
| 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 | CHLORPROPAMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2051 | |
| 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 |
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 | |
| 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 | |
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| Record name | Chlorpropamide [USP:INN:BAN:JAN] | |
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| Record name | Chlorpropamide | |
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| Record name | chlorpropamide | |
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| Record name | CHLORPROPAMIDE | |
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| Record name | Chlorpropamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014810 | |
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Melting Point |
261 to 264 °F (NTP, 1992), 129.2-129.8, 127-129 °C, 127 - 129 °C |
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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| Record name | CHLORPROPAMIDE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2051 | |
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| Record name | Chlorpropamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014810 | |
| 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
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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| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Reactant of Route 1
Reactant of Route 1
Chlorpropamide
Reactant of Route 2
Reactant of Route 2
Chlorpropamide
Reactant of Route 3
Reactant of Route 3
Chlorpropamide
Reactant of Route 4
Reactant of Route 4
Chlorpropamide
Reactant of Route 5
Reactant of Route 5
Chlorpropamide
Reactant of Route 6
Reactant of Route 6
Chlorpropamide
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