Acetazolamide
Overview
Description
Acetazolamide is a carbonic anhydrase inhibitor widely used in the medical field. It is known for its applications in treating glaucoma, epilepsy, acute mountain sickness, periodic paralysis, idiopathic intracranial hypertension, and heart failure. The compound is also used to alkalinize urine . This compound was first introduced in 1952 and is available as a generic medication .
Mechanism of Action
Target of Action
Acetazolamide primarily targets carbonic anhydrase , an enzyme found in many tissues of the body, including the eye and the kidneys . This enzyme plays a crucial role in the regulation of pH and fluid balance .
Mode of Action
This compound works by inhibiting the activity of carbonic anhydrase . This inhibition decreases the formation of hydrogen ions and bicarbonate from carbon dioxide and water . The anticonvulsant activity of this compound may depend on a direct inhibition of carbonic anhydrase in the CNS, which decreases carbon dioxide tension in the pulmonary alveoli, thus increasing arterial oxygen tension .
Pharmacokinetics
This compound is well absorbed orally, with a bioavailability of over 90% . It has a volume of distribution of 0.3 L/kg, and plasma protein binding is 90–95% . An increase in urine pH from bicarbonate diuresis occurs within 30 minutes, is maximal at 2 hours, and persists for 12 hours after a single dose . It is excreted by secretion in the proximal convoluted tubule of the kidney, therefore dosing must be reduced in renal failure .
Action Environment
The efficacy of this compound can be influenced by environmental factors such as altitude. It is firmly established as a first-line prevention for altitude sickness .
Safety and Hazards
Future Directions
Acetazolamide added to intravenous loop diuretics decreases congestion within three days in patients with acute decompensated heart failure . The ADVOR trial examined whether the addition of this compound to intravenous loop diuretics improves decongestion in patients with acute decompensated heart failure .
Biochemical Analysis
Biochemical Properties
Acetazolamide’s major biochemical and pharmacological effect is deemed to be carbonic anhydrase inhibition . It interacts with this enzyme, inhibiting its activity . This interaction plays a significant role in the biochemical reactions involving this compound .
Cellular Effects
This compound has a profound impact on cellular membrane ion/water channel activity . It influences cell function by modulating these channels, which can affect cell signaling pathways, gene expression, and cellular metabolism .
Molecular Mechanism
The molecular mechanism of this compound is primarily based on its inhibition of carbonic anhydrase . This inhibition leads to changes in ion/water channel activity at the cellular membrane, which can result in changes in gene expression .
Temporal Effects in Laboratory Settings
The effects of this compound can change over time in laboratory settings . Information on the product’s stability, degradation, and any long-term effects on cellular function observed in in vitro or in vivo studies is currently being researched .
Dosage Effects in Animal Models
The effects of this compound can vary with different dosages in animal models . Studies are ongoing to determine any threshold effects observed in these studies, as well as any toxic or adverse effects at high doses .
Metabolic Pathways
This compound is involved in metabolic pathways through its interaction with carbonic anhydrase . This interaction can affect metabolic flux or metabolite levels .
Transport and Distribution
It is believed to interact with certain transporters or binding proteins, which could affect its localization or accumulation .
Subcellular Localization
The subcellular localization of this compound and its effects on its activity or function are areas of active research . It is possible that certain targeting signals or post-translational modifications direct it to specific compartments or organelles .
Preparation Methods
Synthetic Routes and Reaction Conditions: The synthesis of acetazolamide involves the oxidation of a thiol derivative to form a sulfonyl chloride intermediate. This intermediate then reacts with various amines, hydrazones, and bis-amine precursors to create new sulfonamide derivatives . The oxidation process can be enhanced by substituting chlorine gas with sodium hypochlorite (commercial bleach), which improves safety and environmental conditions .
Industrial Production Methods: In industrial settings, this compound is produced by mixing this compound with lactose, cornstarch, pregelatinized starch, PVP, sucrose, and carboxymethyl starch sodium. The mixture is then pelletized, dried, and tabletted to obtain this compound tablets .
Chemical Reactions Analysis
Types of Reactions: Acetazolamide undergoes various chemical reactions, including oxidation, reduction, and substitution. The compound is known for its inhibitory effect on carbonic anhydrase, which leads to a decrease in the formation of hydrogen ions and bicarbonate from carbon dioxide and water .
Common Reagents and Conditions:
Oxidation: Sodium hypochlorite (commercial bleach) is used as an oxidizing agent.
Reduction and Substitution: Various amines, hydrazones, and bis-amine precursors are used in the synthesis of new sulfonamide derivatives.
Major Products Formed: The major products formed from these reactions include novel sulfonamide derivatives with enhanced antibacterial and antioxidant properties .
Scientific Research Applications
Acetazolamide has a wide range of scientific research applications:
Chemistry: Used as a carbonic anhydrase inhibitor in various chemical reactions.
Biology: Studied for its effects on cellular membrane ion/water channel activity.
Medicine: Used to treat glaucoma, epilepsy, acute mountain sickness, periodic paralysis, idiopathic intracranial hypertension, and heart failure.
Industry: Utilized in the production of pharmaceuticals and as an antibacterial and antioxidant agent.
Comparison with Similar Compounds
Sulfanilamide: An earlier discovered compound with similar enzymatic inhibitory activity but much less potent than acetazolamide.
Other Sulfonamide Derivatives: Various diuretics and anticonvulsants with minor to moderate carbonic anhydrase activity.
Uniqueness of this compound: this compound stands out due to its potent inhibitory effect on carbonic anhydrase, making it highly effective in treating a wide range of medical conditions. Its ability to act as a diuretic, anticonvulsant, and glaucoma medication highlights its versatility and importance in both clinical and research settings .
Properties
IUPAC Name |
N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
BZKPWHYZMXOIDC-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(=O)NC1=NN=C(S1)S(=O)(=O)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C4H6N4O3S2 |
Source
|
| Record name | ACETAZOLAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/19702 | |
| 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 | |
Related CAS |
1424-27-7 (mono-hydrochloride salt) |
Source
|
| Record name | Acetazolamide [USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000059665 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID7022544 |
Source
|
| Record name | Acetazolamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7022544 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
222.3 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Acetazolamide appears as white to yellowish-white fine crystalline powder. No odor or taste. (NTP, 1992), Solid |
Source
|
| Record name | ACETAZOLAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/19702 | |
| 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 | Acetazolamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014957 | |
| 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 |
>33.3 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 72 °F (NTP, 1992), SPARINGLY SOL IN COLD WATER, SLIGHTLY SOL IN ALCOHOL, INSOL IN CHLOROFORM, DIETHYL ETHER, CARBON TETRACHLORIDE; SLIGHTLY SOL IN ACETONE, Readily soluble in 1 N sodium carbonate solution., In water= 980 mg/l at 30 °C., 2.79e+00 g/L |
Source
|
| Record name | SID855900 | |
| 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 | ACETAZOLAMIDE | |
| 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 | Acetazolamide | |
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| Record name | ACETAZOLAMIDE | |
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| Record name | Acetazolamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014957 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Mechanism of Action |
The anticonvulsant activity of Acetazolamide may depend on a direct inhibition of carbonic anhydrase in the CNS, which decreases carbon dioxide tension in the pulmonary alveoli, thus increasing arterial oxygen tension. The diuretic effect depends on the inhibition of carbonic anhydrase, causing a reduction in the availability of hydrogen ions for active transport in the renal tubule lumen. This leads to alkaline urine and an increase in the excretion of bicarbonate, sodium, potassium, and water., Carbonic anhydrase inhibitors potently inhibit (IC50 for acetazolamide is 10 nM) both the membrane bound and cytoplasmic forms of carbonic anhydrase, resulting in nearly complete abolition of NaHCO3 reabsorption in the proximal tubule. /Carbonic Anhydrase Inhibitors/, Although the proximal tubule is the major site of action of carbonic anhydrase inhibitors, carbonic anhydrase also is involved in secretion of titratable acid in the collecting duct system (a process which involves a proton pump), and therefore the collecting duct system is a secondary site of action for this class of drugs. /Carbonic Anhydrase Inhibitors/, Acetazolamide frequently causes paresthesias and somnolence, suggesting an action of carbonic anhydrase inhibitors in the CNS. The efficacy of acetazolamide in epilepsy is in part due to the production of metabolic acidosis; however, direct actions of acetazolamide in the CNS also contribute to its anticonvulsant action., ... Inhibition of carbonic anhydrase decreases the rate of formation of aqueous humor and consequently reduce intraocular pressure. /Carbonic Anhydrase Inhibitors/, For more Mechanism of Action (Complete) data for ACETAZOLAMIDE (6 total), please visit the HSDB record page. |
Source
|
| Record name | Acetazolamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00819 | |
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| Record name | ACETAZOLAMIDE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3002 | |
| 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 WATER, WHITE TO FAINTLY YELLOWISH WHITE, CRYSTALLINE, POWDER | |
CAS No. |
59-66-5 |
Source
|
| Record name | ACETAZOLAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/19702 | |
| 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 | Acetazolamide | |
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| Record name | Acetazolamide [USP:INN:BAN:JAN] | |
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| Record name | Acetazolamide | |
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| Record name | ACETAZOLAMIDE | |
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| Source | Human Metabolome Database (HMDB) | |
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Melting Point |
496 to 498 °F (effervescence) (NTP, 1992), 258-259 °C (EFFERVESCENCE), 260.5 °C |
Source
|
| Record name | ACETAZOLAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/19702 | |
| 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 | Acetazolamide | |
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| Record name | Acetazolamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014957 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
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Feasible Synthetic Routes
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