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    Estazolam molecular structure

    Estazolam Stats & Data

    Prosom Eurodin Elprazolam
    NPS DataHub
    MW294.74
    FormulaC16H11ClN4
    CAS29975-16-4
    IUPAC8-Chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
    SMILESClc1ccc2n3cnnc3CN=C(c3ccccc3)c2c1
    InChIKeyCDCHDCWJMGXXRH-UHFFFAOYSA-N
    2020/3. Benzodiazepine; 2021/3. Benzodiazepine; 2022/3. Benzodiazepine
    Chemical Class Benzodiazepine
    Psychoactive Class Depressant

    Pharmacology

    DrugBank
    Protein binding 93% protein bound, independant of concentration. State Solid

    Description

    A benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam.

    Mechanism of Action

    Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

    Pharmacodynamics

    Estazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam.

    Metabolism

    Extensively metabolized in the liver. In vitro studies with human liver microsomes indicate that the biotransformation of estazolam to the major circulating metabolite 4-hydroxy-estazolam is mediated by cytochrome P450 3A (CYP3A).

    Absorption

    Tablets have been found to be equivalent in absorption to an orally administered solution of estazolam. In healthy subjects who received up to three times the recommended dose, peak estazolam plasma concentrations occurred within two hours after dosing (range 0.5 to 6.0 hours) and were proportional to the administered dose, suggesting linear pharmacokinetics over the dosage range tested.

    Toxicity

    Symptoms of overdose include confusion, depressed breathing, drowsiness and eventually coma, lack of coordination, and slurred speech.

    Indication

    For the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings.

    Half-life

    The range of estimates for the mean elimination half-life of estazolam varies from 10 to 24 hours.

    Elimination

    Estazolam is extensively metabolized. The elimination of the parent drug takes place via hepatic metabolism of estazolam to hydroxylated and other metabolites that are eliminated largely in the urine both free and conjugated. Less than 5% of a 2 mg dose of estazolam was excreted unchanged in the urine, with only 4% of the dose appearing in the feces. Radiolabel mass balance studies indicate that the main route of excretion is via the kidneys. After 5 days, 87% of the administered radioactivity was excreted in human urine. Less than 4% of the dose was excreted unchanged.

    Effect Profile

    Curated
    Benzodiazepine 7.4

    Strong anxiolysis and euphoria with mild cognitive impairment, low sedation

    Anxiolysis×3
    10
    Sedation / Relaxation×2
    3
    Motor / Cognitive Impairment×1
    4
    Euphoria / Mood Lift×1
    10

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 3d Half tolerance 37d Baseline ~60d
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