Hydrochlorothiazide
概要
説明
ヒドロクロロチアジドは、主に高血圧（高血圧）および浮腫（体液貯留）の治療に処方される広く使用されているチアジド系利尿薬です。 糖尿病性尿崩症や腎尿細管性アシドーシスなどの状態の管理や、尿中カルシウムレベルが高い個人の腎臓結石のリスクを軽減するためにも使用されます 。 ヒドロクロロチアジドは、腎臓でのナトリウムイオンと塩化物イオンの再吸収を阻害することにより作用し、尿の産生量を増やし、血漿量を減少させます .
2. 製法
合成経路と反応条件： ヒドロクロロチアジドは、複数段階の化学プロセスによって合成されます。合成は通常、3-クロロアニリンとクロロスルホン酸の反応により、3-クロロ-4-スルファモイルアニリンを形成することから始まります。 この中間体は次に、チオ尿素と環化されてチアジド環構造を生成し、ヒドロクロロチアジドが得られます .
工業生産方法： ヒドロクロロチアジドの工業生産は、同様の合成経路で行われますが、より大規模に行われます。 プロセスは高収率と高純度のために最適化されており、精製と品質管理のために、高速液体クロマトグラフィー（HPLC）などの高度な技術が使用されることがよくあります .
作用機序
ヒドロクロロチアジドは、腎臓の遠位尿細管におけるナトリウム-塩化物共輸送体を阻害することにより作用します。この阻害により、ナトリウムイオンと塩化物イオンの再吸収が阻止され、これらのイオンと水が増加して排泄されます。 その結果生じる利尿効果は、血漿量を減らし、末梢血管抵抗を低下させ、血圧を下げます 。 さらに、ヒドロクロロチアジドのイオン輸送への作用は、電解質バランスと腎機能に影響を与える可能性があります .
6. 類似の化合物との比較
ヒドロクロロチアジドは、クロロチアジド、クロルタリドン、インダパミドなどの類似の化合物を含むチアジド系利尿薬クラスに属します。 これらの化合物と比較して、ヒドロクロロチアジドは、比較的短い半減期と速やかな作用開始が知られています .
類似の化合物：
クロロチアジド： より長い半減期を持つ別のチアジド系利尿薬。
クロルタリドン： より長い作用時間とより高い効力が知られています。
インダパミド： 血管拡張作用を追加したチアジド系利尿薬.
準備方法
Synthetic Routes and Reaction Conditions: Hydrochlorothiazide is synthesized through a multi-step chemical process. The synthesis typically involves the reaction of 3-chloroaniline with chlorosulfonic acid to form 3-chloro-4-sulfamoylaniline. This intermediate is then cyclized with thiourea to produce the thiazide ring structure, resulting in this compound .
Industrial Production Methods: Industrial production of this compound involves similar synthetic routes but on a larger scale. The process is optimized for high yield and purity, often involving advanced techniques such as high-performance liquid chromatography (HPLC) for purification and quality control .
化学反応の分析
反応の種類： ヒドロクロロチアジドは、以下を含むさまざまな化学反応を起こします。
酸化： ヒドロクロロチアジドは、特定の条件下で酸化され、スルホキシドやスルホンを生成します。
還元： 還元反応は、ヒドロクロロチアジ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などがあります。
還元： 水素化リチウムアルミニウムと水素化ホウ素ナトリウムなどの還元剤が使用されます。
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： 置換チアジド誘導体.
4. 科学研究への応用
ヒドロクロロチアジドは、幅広い科学研究への応用があります。
化学： 利尿薬機構と薬物相互作用の研究におけるモデル化合物として使用されます。
生物学： 細胞イオン輸送と電解質バランスへの影響が調べられています。
医学： 高血圧、心不全、腎臓疾患における治療効果について広く研究されています。
科学的研究の応用
Hydrochlorothiazide has a wide range of scientific research applications:
Chemistry: Used as a model compound in studies of diuretic mechanisms and drug interactions.
Biology: Investigated for its effects on cellular ion transport and electrolyte balance.
Medicine: Extensively studied for its therapeutic effects in hypertension, heart failure, and kidney disorders.
Industry: Utilized in the development of combination drug therapies and pharmaceutical formulations.
類似化合物との比較
Chlorothiazide: Another thiazide diuretic with a longer half-life.
Chlorthalidone: Known for its longer duration of action and greater potency.
Indapamide: A thiazide-like diuretic with additional vasodilatory properties.
Hydrochlorothiazide’s unique balance of efficacy, safety, and cost-effectiveness makes it a widely preferred choice for managing hypertension and edema .
特性
IUPAC Name |
6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C7H8ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-2,10-11H,3H2,(H2,9,12,13) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
JZUFKLXOESDKRF-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1NC2=CC(=C(C=C2S(=O)(=O)N1)S(=O)(=O)N)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C7H8ClN3O4S2 |
Source
|
| Record name | HYDROCHLOROTHIAZIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20489 | |
| 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 | hydrochlorothiazide | |
| Source | Wikipedia | |
| URL | https://en.wikipedia.org/wiki/Hydrochlorothiazide | |
| Description | Chemical information link to Wikipedia. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID2020713 |
Source
|
| Record name | Hydrochlorothiazide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2020713 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
297.7 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Crystals or white powder. (NTP, 1992), Solid |
Source
|
| Record name | HYDROCHLOROTHIAZIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20489 | |
| 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 | Hydrochlorothiazide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001928 | |
| 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 |
>44.7 [ug/mL] (The mean of the results at pH 7.4), less than 0.1 mg/mL at 72.5 °F (NTP, 1992), In water, 722 mg/L at 25 °C, Soluble in ethanol at approximately 750 g/L; soluble in acetone, dilute ammonia; freely soluble in sodium hydroxide solution, n-butylamine, dimethylformamide; sparingly soluble in alcohol; insoluble in ether, chloroform, dilute mineral acids, Soluble in sodium hydroxide solution, Freely soluble in sodium hydroxide solution, in n-butylamine and in dimethylformamide; sparingly soluble in methanol; insoluble in dilute mineral acids, 0.722 mg/mL at 25 °C |
Source
|
| Record name | SID855646 | |
| 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 | HYDROCHLOROTHIAZIDE | |
| 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 | Hydrochlorothiazide | |
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| URL | https://www.drugbank.ca/drugs/DB00999 | |
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| Record name | Hydrochlorothiazide | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3096 | |
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| Record name | Hydrochlorothiazide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001928 | |
| 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. | |
Density |
1.693 g/cu cm |
Source
|
| Record name | Hydrochlorothiazide | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3096 | |
| 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 |
Hydrochlorothiazide is transported from the circulation into epithelial cells of the distal convoluted tubule by the organic anion transporters OAT1, OAT3, and OAT4. From these cells, hydrochlorothiazide is transported to the lumen of the tubule by multidrug resistance associated protein 4 (MRP4). Normally, sodium is reabsorbed into epithelial cells of the distal convoluted tubule and pumped into the basolateral interstitium by a sodium-potassium ATPase, creating a concentration gradient between the epithelial cell and the distal convoluted tubule that promotes the reabsorption of water. Hydrochlorothiazide acts on the proximal region of the distal convoluted tubule, inhibiting reabsorption by the sodium-chloride symporter, also known as Solute Carrier Family 12 Member 3 (SLC12A3). Inhibition of SLC12A3 reduces the magnitude of the concentration gradient between the epithelial cell and distal convoluted tubule, reducing the reabsorption of water. |
Source
|
| Record name | Hydrochlorothiazide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00999 | |
| 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. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
Color/Form |
White, or practically white crystalline powder, White to off-white crystalline powder | |
CAS No. |
58-93-5 |
Source
|
| Record name | HYDROCHLOROTHIAZIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20489 | |
| 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 | Hydrochlorothiazide | |
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| Record name | Hydrochlorothiazide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00999 | |
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| Record name | 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3,4-dihydro-, 1,1-dioxide | |
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| Record name | Hydrochlorothiazide | |
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| Record name | Hydrochlorothiazide | |
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| Record name | HYDROCHLOROTHIAZIDE | |
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| Record name | Hydrochlorothiazide | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3096 | |
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| Record name | Hydrochlorothiazide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001928 | |
| 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 |
523 to 527 °F (NTP, 1992), 266-268, 273-275 °C, 274 °C |
Source
|
| Record name | HYDROCHLOROTHIAZIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20489 | |
| 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 | Hydrochlorothiazide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00999 | |
| 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 | Hydrochlorothiazide | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3096 | |
| 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 | Hydrochlorothiazide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001928 | |
| 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. | |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
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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 Hydrochlorothiazide exert its antihypertensive effect?
A1: this compound (HCTZ) primarily acts on the distal convoluted tubule in the kidneys to inhibit sodium and chloride reabsorption. This leads to increased sodium and water excretion, thereby reducing blood volume and lowering blood pressure. [, , , ]
Q2: Does this compound have any impact on the renin-angiotensin-aldosterone system?
A2: While HCTZ's primary mechanism doesn't directly involve the renin-angiotensin-aldosterone system, its diuretic effect can lead to a compensatory increase in plasma renin activity and aldosterone levels. [] This can sometimes counteract its blood pressure-lowering effects. [, ]
Q3: Are there any studies comparing this compound with other diuretics like indapamide?
A3: Yes, a study compared the hypotensive, metabolic, and endothelial effects of indapamide-retard and HCTZ. Despite similar blood pressure-lowering effects, indapamide showed a more favorable metabolic profile, with no significant elevation of triglycerides or glucose, unlike HCTZ. []
Q4: What is the molecular formula and weight of this compound?
A4: The molecular formula of this compound is C12H11ClN3O4S2, and its molecular weight is 353.82 g/mol.
Q5: Can Raman spectroscopy be used to study this compound inclusion complexes?
A5: Yes, Raman spectroscopy has been successfully used to study the formation of inclusion complexes between this compound and β-cyclodextrin. The technique confirmed the presence of hydrogen bonds between the drug and the cyclodextrin molecule. []
Q6: What analytical methods are commonly used to quantify this compound in pharmaceutical formulations?
A6: Several analytical methods are employed to quantify HCTZ in pharmaceutical formulations, including:
- High-Performance Liquid Chromatography (HPLC): This versatile technique allows simultaneous determination of HCTZ with other antihypertensive drugs like amlodipine, valsartan, and quinapril. [, , , ]
- UV Spectrophotometry: This method offers simplicity and cost-effectiveness for HCTZ quantification, either alone or in combination with other drugs like losartan potassium. [, ]
- High-Performance Thin Layer Chromatography (HPTLC): HPTLC provides a rapid and precise alternative for analyzing HCTZ in tablet formulations, often alongside drugs like candesartan cilexetil. []
Q7: What formulation strategies are used to improve the dissolution and bioavailability of this compound?
A7: Direct powder compression using disintegrants like croscarmellose sodium (CMS-Na) and low-substituted hydroxypropyl cellulose (L-HPC) has shown promise in improving the dissolution rate of this compound dispersible tablets. []
Q8: Are there studies on the stability of this compound under various stress conditions?
A8: Yes, stability-indicating HPLC methods have been developed and validated to assess the stability of this compound under various stress conditions like acidic, basic, oxidative, thermal, and photolytic degradation. These methods ensure the accurate determination of the drug in the presence of its degradation products. [, ]
Q9: What is the duration of action of this compound?
A9: this compound typically has a duration of action of 6 to 12 hours, but its blood pressure-lowering effect may persist for longer. [, , ]
Q10: Does this compound effectively lower both systolic and diastolic blood pressure?
A10: Clinical trials have shown that HCTZ effectively reduces both systolic and diastolic blood pressure, although a higher dose might be needed for optimal control in some patients, especially when combined with other antihypertensives. [, ]
Q11: Are there any studies investigating the long-term effects of this compound on renal hemodynamics?
A11: Research indicates that long-term HCTZ treatment in essential hypertension may positively impact renal hemodynamics, potentially reversing some of the abnormalities associated with the condition. These effects go beyond simple blood pressure reduction and may involve humoral and neural mechanisms. []
Q12: What is the comparative efficacy of this compound combined with other antihypertensives?
A12: Several studies have compared HCTZ combinations with other antihypertensive regimens:
- HCTZ + Ramipril: This combination demonstrated superior antihypertensive effects compared to HCTZ alone, particularly on nocturnal blood pressure, with significant reductions in plasma angiotensin II and aldosterone levels. []
- HCTZ + Amlodipine: This combination, in a fixed-dose triple therapy with valsartan, showed no significant pharmacokinetic interactions and exhibited favorable safety and tolerability profiles. []
- HCTZ + Losartan Potassium: This combination proved effective and well-tolerated in hypertensive patients, with a smooth 24-hour blood pressure control. []
Q13: Are there any concerns about this compound causing electrolyte imbalances?
A13: One notable concern with this compound is its potential to cause hypokalemia (low potassium levels), especially with higher doses or prolonged use. [, , ] This is primarily due to increased potassium excretion through the kidneys.
Q14: What is the impact of this compound on serum potassium levels?
A14: Studies highlight the significant impact of HCTZ on serum potassium, with a high prevalence of hypokalemia observed in hypertensive patients treated with this drug. This emphasizes the importance of potassium level monitoring during therapy. []
Q15: Does combining this compound with other drugs affect its potassium-lowering effect?
A15: Combining HCTZ with certain medications can influence its effects on potassium levels:
- Enalapril: Co-administration of enalapril with HCTZ appears to offer a protective effect against hypokalemia, potentially mitigating potassium loss induced by HCTZ. [, ]
- Amiloride: Similarly, the addition of amiloride to HCTZ therapy can help prevent severe hypokalemia and alkalosis that might arise from using HCTZ alone. [, ]
Q16: Are there any ongoing large-scale studies comparing the cardiovascular outcomes of chlorthalidone and this compound?
A17: Yes, the Diuretic Comparison Project (VA Cooperative Study 597) is a large randomized trial aiming to directly compare the effects of chlorthalidone and HCTZ on cardiovascular outcomes in older patients with hypertension. [] This landmark study promises valuable insights into the long-term efficacy and safety of these commonly prescribed diuretics.
Q17: What are the potential advantages of fixed-dose combination therapies incorporating this compound?
A17: Fixed-dose combinations like those containing HCTZ with amlodipine, valsartan, or losartan potassium present several advantages:
- Improved Patient Compliance: Single-pill combinations can enhance medication adherence by simplifying dosing regimens. []
- Synergistic Effects: Combining drugs with different mechanisms of action can lead to enhanced blood pressure control and potentially lower the required doses of individual components. [, ]
- Cost-Effectiveness: Fixed-dose combinations might offer economic benefits compared to using multiple separate medications. []
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