molecular formula C4H6N4O3S2 B1664987 Acétazolamide CAS No. 59-66-5

Acétazolamide

Numéro de catalogue: B1664987
Numéro CAS: 59-66-5
Poids moléculaire: 222.3 g/mol
Clé InChI: BZKPWHYZMXOIDC-UHFFFAOYSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
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Description

L’acétazolamide est un inhibiteur de l’anhydrase carbonique largement utilisé dans le domaine médical. Il est connu pour ses applications dans le traitement du glaucome, de l’épilepsie, du mal des montagnes aigu, de la paralysie périodique, de l’hypertension intracrânienne idiopathique et de l’insuffisance cardiaque. Le composé est également utilisé pour alcaliniser l’urine . L’this compound a été introduit pour la première fois en 1952 et est disponible sous forme de médicament générique .

Analyse Biochimique

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 Acetazolamide .

Cellular Effects

Acetazolamide 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 Acetazolamide 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 Acetazolamide 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 Acetazolamide 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

Acetazolamide 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 Acetazolamide 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 .

Méthodes De Préparation

Voies de synthèse et conditions réactionnelles : La synthèse de l’acétazolamide implique l’oxydation d’un dérivé thiolique pour former un intermédiaire chlorure de sulfonyle. Cet intermédiaire réagit ensuite avec diverses amines, hydrazones et précurseurs de bis-amines pour créer de nouveaux dérivés de sulfonamide . Le processus d’oxydation peut être amélioré en remplaçant le chlore gazeux par de l’hypochlorite de sodium (eau de Javel commerciale), ce qui améliore la sécurité et les conditions environnementales .

Méthodes de production industrielle : Dans les milieux industriels, l’this compound est produit en mélangeant de l’this compound avec du lactose, de l’amidon de maïs, de l’amidon pré-gélatinisé, du PVP, du saccharose et de l’amidon de carboxymethylsodium. Le mélange est ensuite granulé, séché et comprimé pour obtenir des comprimés d’this compound .

Comparaison Avec Des Composés Similaires

Uniqueness of Acetazolamide: Acetazolamide 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 .

Propriétés

IUPAC Name

N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
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 PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

BZKPWHYZMXOIDC-UHFFFAOYSA-N
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 PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C4H6N4O3S2
Record name ACETAZOLAMIDE
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Related CAS

1424-27-7 (mono-hydrochloride salt)
Record name Acetazolamide [USP:INN:BAN:JAN]
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DSSTOX Substance ID

DTXSID7022544
Record name Acetazolamide
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Molecular Weight

222.3 g/mol
Source PubChem
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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
Record name ACETAZOLAMIDE
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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
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Record name ACETAZOLAMIDE
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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.
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Color/Form

CRYSTALS FROM WATER, WHITE TO FAINTLY YELLOWISH WHITE, CRYSTALLINE, POWDER

CAS No.

59-66-5
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Melting Point

496 to 498 °F (effervescence) (NTP, 1992), 258-259 °C (EFFERVESCENCE), 260.5 °C
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Synthesis routes and methods

Procedure details

AL4414A; diclofenamide; dorzolamide; methazolamide; sezolamide; sulocarbilate.
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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

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