雷尼替丁
描述
雷尼替丁是一种广泛用于减少胃酸产生的组胺H2受体拮抗剂。它通常被用于治疗消化性溃疡病、胃食管反流病和卓-艾综合征。雷尼替丁于1976年在英国被发现，并于1981年投入商业使用。 它在市场上以赞塔克等品牌名称销售 .
作用机制
雷尼替丁通过阻断胃壁上的组胺H2受体起作用。从嗜铬细胞样细胞释放的组胺与这些受体结合并刺激胃酸分泌。 通过阻断这些受体，雷尼替丁减少胃酸的产生，从而缓解与胃酸过多相关的症状 .
科学研究应用
生化分析
Biochemical Properties
Ranitidine works by blocking the action of histamine on the H2 receptors of the parietal cells in the stomach, thereby reducing the production of stomach acid. The compound interacts with these receptors, preventing histamine from binding and triggering acid production .
Cellular Effects
Ranitidine’s primary effect on cells is the reduction of gastric acid secretion in parietal cells. This can influence various cellular processes, including the regulation of intracellular pH and the activation of certain enzymes that require an acidic environment .
Molecular Mechanism
The molecular mechanism of Ranitidine involves its binding to H2 receptors on the parietal cells of the stomach. This prevents histamine from binding to these receptors and triggering the secretion of gastric acid. This action does not involve enzyme inhibition or activation, but rather receptor antagonism .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of Ranitidine are observed to be relatively stable over time. The drug does not undergo significant degradation and continues to exert its acid-suppressing effects as long as it is present in the system .
Dosage Effects in Animal Models
In animal models, the effects of Ranitidine have been observed to be dose-dependent. Higher doses result in greater suppression of gastric acid secretion. Extremely high doses may lead to adverse effects, although these are generally rare .
Metabolic Pathways
Ranitidine is metabolized in the liver through the cytochrome P450 system. It does not significantly interact with or alter other metabolic pathways .
Transport and Distribution
After oral administration, Ranitidine is absorbed in the gastrointestinal tract and distributed throughout the body. It can cross cell membranes and reach its site of action in the stomach .
Subcellular Localization
Ranitidine acts on the cell surface, specifically on the H2 receptors of parietal cells in the stomach. It does not have a specific subcellular localization as its site of action is on the cell surface .
准备方法
合成路线和反应条件： 雷尼替丁可以通过多种途径合成。一种常见的方法涉及中间体5-(二甲基氨基)糠基硫乙胺。合成从糠醇开始，经历一系列反应形成中间体。 然后将该中间体与1-甲硫基-1-(N-甲基氨基)-2-硝基乙烯反应生成雷尼替丁 .
工业生产方法： 雷尼替丁的工业生产通常涉及使用有机溶剂和中等反应条件。 例如，该化合物可以通过在有机溶剂（如二甲基甲酰胺）中用N，N-二甲基氨基三苯基膦盐和二甲胺在约90°C下处理中间体来合成 .
化学反应分析
反应类型： 雷尼替丁经历多种化学反应，包括：
氧化： 雷尼替丁在特定条件下会氧化，导致形成不同的副产物。
常用试剂和条件：
氧化： 常用的氧化剂可用于氧化雷尼替丁。
光解： 光解反应通常需要暴露于光线下，并且会受到天然有机物存在的影响。
主要形成的产物：
氧化： 形成的各种氧化产物取决于使用的具体条件和试剂。
光解： 雷尼替丁的光解会导致形成多种降解产物.
相似化合物的比较
雷尼替丁属于组胺H2受体拮抗剂类，其中还包括西咪替丁和法莫替丁等化合物。
类似化合物：
西咪替丁： 首个被发现的H2受体拮抗剂。它具有相似的作用机制，但化学结构不同。
雷尼替丁的独特之处： 雷尼替丁因其改善的副作用谱和效力而比西咪替丁更受欢迎。 由于担心雷尼替丁产品中存在N-亚硝基二甲胺，导致其在许多市场上被撤回 .
属性
IUPAC Name |
(E)-1-N'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+ |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
VMXUWOKSQNHOCA-UKTHLTGXSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CNC(=C[N+](=O)[O-])NCCSCC1=CC=C(O1)CN(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CN/C(=C\[N+](=O)[O-])/NCCSCC1=CC=C(O1)CN(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C13H22N4O3S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID101112063 |
Source
|
| Record name | (1E)-N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID101112063 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
314.41 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Ranitidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001930 | |
| 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 |
Water soluble |
Source
|
| Record name | RANITIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3925 | |
| 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 |
H2 antagonists inhibit gastric acid secretion elicited by histamine and other H2 agonists in a dose dependent, competitive manner; the degree of inhibition parallels the concentration of the drug in plasma over a wide range. The H2 antagonists also inhibit acid secretion elicited by gastrin and, to a lesser extent, by muscarinic agonists. Importantly, these drugs inhibit basal (fasting) and nocturnal acid secretion and that stimulated by food, sham feeding, fundic distention, and various pharmacological agents; this property reflects the vital role of histamine in mediating the effects of diverse stimuli. /H2 Receptor Antagonists/, ... /H2 Antagonists/ measurably inhibit effects on the cardiovascular and other systems that are elicited through H2 receptors by exogenous or endogenous histamine. /H2 Receptor Antagonists/, ...IS A COMPETITIVE ANTAGONIST OF HISTAMINE-INDUCED GASTRIC ACID SECRETION... INHIBITS BOTH THE VOLUME AND CONCENTRATION OF GASTRIC ACID INDUCED NOCTURNALLY AND BY FOOD BUT DOES NOT AFFECT GASTRIC MUCUS OR ITS PRODUCTION. ...DOES NOT AFFECT LOWER ESOPHAGEAL SPHINCTER PRESSURE... |
Source
|
| Record name | RANITIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3925 | |
| 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 |
SOLID | |
CAS No. |
82530-72-1, 66357-35-5 |
Source
|
| Record name | (1E)-N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=82530-72-1 | |
| 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. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | ranitidine | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=757851 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | (1E)-N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID101112063 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Ranitidine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.060.283 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | RANITIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3925 | |
| 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. | |
| Record name | Ranitidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001930 | |
| 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. | |
Melting Point |
69-70 °C, MP: 133-134 °C /RATINIDINE HYDROCHLORIDE/ |
Source
|
| Record name | RANITIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3925 | |
| 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. | |
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
Q1: How does ranitidine exert its therapeutic effect?
A: Ranitidine acts as a competitive antagonist at histamine H2 receptors found on the basolateral membrane of parietal cells in the stomach. [] By blocking histamine binding to these receptors, ranitidine effectively reduces the secretion of gastric acid, providing relief from symptoms associated with hyperacidity. []
Q2: What are the key pharmacokinetic properties of ranitidine?
A: Ranitidine is well absorbed after oral administration, reaching peak plasma concentrations within 1-3 hours. [] It is metabolized in the liver to several metabolites, with the primary metabolite being desmethylranitidine. [] Approximately 77% of an administered dose is excreted unchanged in the urine, with the remainder excreted as metabolites. [] The elimination half-life of ranitidine is 2.9-3.9 hours. []
Q3: Does ranitidine interact with other drugs?
A: Yes, ranitidine has been shown to interact with several drugs, primarily through its effects on drug-metabolizing enzymes in the liver. [] It can inhibit the cytochrome P450 enzyme system, particularly the CYP1A2 and CYP2D6 isoenzymes. [] This inhibition can lead to increased plasma concentrations of drugs that are metabolized by these enzymes, potentially resulting in adverse effects.
Q4: What are the safety concerns associated with ranitidine use?
A: While generally well-tolerated, ranitidine has been associated with rare but potentially serious adverse effects, including hypersensitivity reactions, hematological abnormalities, and hepatic dysfunction. [, ] Furthermore, the detection of N-nitrosodimethylamine (NDMA), a probable human carcinogen, in certain ranitidine formulations has raised concerns about potential long-term risks. []
Q5: What formulations of ranitidine are available?
A: Ranitidine is available in various formulations, including oral tablets, effervescent tablets, syrups, and solutions for intravenous administration. [] The choice of formulation depends on the patient's age, medical condition, and preference.
Q6: What are the main therapeutic applications of ranitidine?
A6: Ranitidine was widely prescribed for conditions associated with gastric hyperacidity, such as:
- Duodenal and gastric ulcers: Clinical trials demonstrated the efficacy of ranitidine in promoting ulcer healing and relieving symptoms. [, ]
- Gastroesophageal reflux disease (GERD): Ranitidine effectively reduces heartburn and other symptoms of GERD. []
- Zollinger-Ellison syndrome: This rare condition involves excessive gastric acid production, and ranitidine can help manage symptoms. []
Q7: What alternatives to ranitidine are available for treating acid-related disorders?
A7: Several alternatives to ranitidine are available, including:
- Proton pump inhibitors (PPIs): These drugs, such as omeprazole, lansoprazole, and esomeprazole, are more potent inhibitors of gastric acid secretion than H2-receptor antagonists. []
- Antacids: These over-the-counter medications provide rapid but short-term relief from heartburn and indigestion by neutralizing stomach acid. []
- Alginates: These medications form a protective barrier over the stomach contents, preventing acid reflux into the esophagus. []
体外研究产品的免责声明和信息
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