Hydrochlorothiazide
Übersicht
Beschreibung
Hydrochlorothiazide is a widely used thiazide diuretic medication primarily prescribed for the treatment of hypertension (high blood pressure) and edema (fluid retention). It is also used to manage conditions such as diabetes insipidus and renal tubular acidosis, and to reduce the risk of kidney stones in individuals with high calcium levels in their urine . This compound works by inhibiting the reabsorption of sodium and chloride ions in the kidneys, leading to increased urine production and decreased blood volume .
Wirkmechanismus
Target of Action
Hydrochlorothiazide primarily targets the sodium-chloride symporter (also known as the Na-Cl cotransporter or NCC) . This protein is located in the distal convoluted tubules of the kidneys . The NCC plays a crucial role in the reabsorption of sodium and chloride ions from the filtrate back into the bloodstream .
Mode of Action
This compound acts as a thiazide diuretic , which means it inhibits the function of the NCC . By blocking the NCC, this compound prevents the reabsorption of sodium and chloride ions . This action leads to an increase in the excretion of these ions, along with water, in the urine . The overall effect is a decrease in the volume of fluid flowing through the blood vessels .
Biochemical Pathways
The primary biochemical pathway affected by this compound is the sodium and chloride reabsorption pathway in the kidneys . By inhibiting the NCC, this compound disrupts this pathway, leading to increased sodium, chloride, and water excretion . This diuretic effect can lead to a decrease in blood volume and a reduction in blood pressure .
Pharmacokinetics
After oral administration, this compound is absorbed via the gastrointestinal tract . It undergoes minimal metabolism and is primarily excreted as the unchanged parent molecule via urine . The duration of action is typically between 8 to 12 hours .
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. For instance, the drug’s absorption can be affected by the pH level in the gastrointestinal tract . Furthermore, the Predicted Environmental Concentration (PEC) / Predicted No Effect Concentration (PNEC) ratio suggests that the use of this compound presents an insignificant risk to the environment .
Vorbereitungsmethoden
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 .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Hydrochlorothiazid unterliegt verschiedenen chemischen Reaktionen, darunter:
Oxidation: Hydrochlorothiazid kann unter bestimmten Bedingungen oxidiert werden, was zur Bildung von Sulfoxiden und Sulfonen führt.
Reduktion: Reduktionsreaktionen können Hydrochlorothiazid in seine entsprechenden Amin-Derivate umwandeln.
Substitution: Nucleophile Substitutionsreaktionen können an der Chlorgruppe auftreten, was zur Bildung verschiedener substituierter Derivate führt.
Häufige Reagenzien und Bedingungen:
Oxidation: Häufige Oxidationsmittel sind Wasserstoffperoxid und Kaliumpermanganat.
Reduktion: Als Reduktionsmittel werden Lithiumaluminiumhydrid und Natriumborhydrid verwendet.
Substitution: Nucleophile wie Amine und Thiole werden in Substitutionsreaktionen eingesetzt.
Hauptprodukte:
Oxidation: Sulfoxide und Sulfone.
Reduktion: Amin-Derivate.
Substitution: Substituierte Thiazid-Derivate.
Wissenschaftliche Forschungsanwendungen
Hydrochlorothiazid hat eine breite Palette von Anwendungen in der wissenschaftlichen Forschung:
Chemie: Wird als Modellverbindung in Studien zu Diuretika-Mechanismen und Arzneimittelwechselwirkungen verwendet.
Biologie: Untersucht wegen seiner Auswirkungen auf den zellulären Ionentransport und den Elektrolythaushalt.
Medizin: Weitgehend untersucht wegen seiner therapeutischen Wirkungen bei Bluthochdruck, Herzinsuffizienz und Nierenerkrankungen.
Industrie: Verwendung bei der Entwicklung von Kombinationsarzneimitteltherapien und pharmazeutischen Formulierungen.
5. Wirkmechanismus
Hydrochlorothiazid entfaltet seine Wirkung, indem es den Natrium-Chlorid-Symporter in den distalen gewundenen Tubuli der Nieren hemmt. Diese Hemmung verhindert die Reabsorption von Natrium- und Chloridionen, was zu einer erhöhten Ausscheidung dieser Ionen zusammen mit Wasser führt. Die resultierende diuretische Wirkung reduziert das Blutvolumen und senkt den peripheren Gefäßwiderstand, wodurch der Blutdruck gesenkt wird . Darüber hinaus kann die Wirkung von Hydrochlorothiazid auf den Ionentransport den Elektrolythaushalt und die Nierenfunktion beeinflussen .
Vergleich Mit ähnlichen Verbindungen
Hydrochlorothiazid gehört zur Klasse der Thiazid-Diuretika, die ähnliche Verbindungen wie Chlorothiazid, Chlorthalidon und Indapamid umfasst. Im Vergleich zu diesen Verbindungen ist Hydrochlorothiazid bekannt für seine relativ kurze Halbwertszeit und den schnellen Wirkungseintritt .
Ähnliche Verbindungen:
Chlorothiazid: Ein weiteres Thiazid-Diuretikum mit einer längeren Halbwertszeit.
Chlorthalidon: Bekannt für seine längere Wirkdauer und größere Potenz.
Indapamid: Ein Thiazid-ähnliches Diuretikum mit zusätzlichen vasodilatierenden Eigenschaften.
Die einzigartige Balance von Wirksamkeit, Sicherheit und Wirtschaftlichkeit von Hydrochlorothiazid macht es zu einer weit verbreiteten Wahl für die Behandlung von Bluthochdruck und Ödemen .
Eigenschaften
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 | |
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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 | |
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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 | |
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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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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 | |
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| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | HYDROCHLOROTHIAZIDE | |
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| Record name | Hydrochlorothiazide | |
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| Record name | Hydrochlorothiazide | |
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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 | |
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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. |
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| Record name | Hydrochlorothiazide | |
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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 | |
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Melting Point |
523 to 527 °F (NTP, 1992), 266-268, 273-275 °C, 274 °C |
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| Record name | HYDROCHLOROTHIAZIDE | |
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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 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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