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    Atomoxetine molecular structure

    Atomoxetine Stats & Data

    Strattera
    NPS DataHub
    MW255.36
    FormulaC17H21NO
    CAS83015-26-3
    IUPAC(3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine
    SMILESCNCCC(Oc1ccccc1C)c1ccccc1
    InChIKeyVHGCDTVCOLNTBX-QGZVFWFLSA-N
    Psychoactive Class Stimulant

    Pharmacology

    DrugBank
    State Solid

    Description

    Atomoxetine is a selective norepinephrine (NE) reuptake inhibitor used for the treatment of attention deficit hyperactivity disorder (ADHD). Also known as the marketed product Strattera, atomoxetine is used with other treatment modalities (psychological, educational, cognitive behaviour therapy, etc) to improve developmentally inappropriate symptoms associated with ADHD including distractibility, short attention span, hyperactivity, emotional lability, and impulsivity. Although the underlying pathophysiology that causes ADHD remains unclear, evidence suggests that dysregulation in noradrenergic and dopaminergic pathways plays a critical role in suboptimal executive functioning within prefrontal regions of the brain, which are involved in attention and memory. Atomoxetine has been shown to specifically increase NA and DA within the prefrontal cortex, but not in the nucleus accumbens (NA) or striatum. This is beneficial in the treatment of ADHD as DA activation in the subcortical NA and striatum is associated with many stimulant-associated side effects and an increase in abuse potential, which is a limiting factor associated with the use of stimulant medications such as DB00422, DB01576, and DB01255. Use of non-stimulant medications such as atomoxetine is therefore thought to offer a clinical advantage over the use of traditional medications for the management of ADHD.

    Mechanism of Action

    Atomoxetine is known to be a potent and selective inhibitor of the norepinephrine transporter (NET), which prevents cellular reuptake of norepinephrine throughout the brain, which is thought to improve the symptoms of ADHD. More recently, positron emission tomography (PET) imaging studies in rhesus monkeys have shown that atomoxetine also binds to the serotonin transporter (SERT), and blocks the N-methyl-d-aspartate (NMDA) receptor, indicating a role for the glutamatergic system in the pathophysiology of ADHD.

    Pharmacodynamics

    Atomoxetine is a selective norepinephrine (NE) reuptake inhibitor used for the treatment of attention deficit hyperactivity disorder (ADHD). Atomoxetine has been shown to specifically increase norepinephrine and dopamine within the prefrontal cortex, which results in improved ADHD symptoms. Due to atomoxetine's noradrenergic activity, it also has effects on the cardiovascular system such as increased blood pressure and tachycardia. Sudden deaths, stroke, and myocardial infarction have been reported in patients taking atomoxetine at usual doses for ADHD. Atomoxetine should be used with caution in patients whose underlying medical conditions could be worsened by increases in blood pressure or heart rate such as certain patients with hypertension, tachycardia, or cardiovascular or cerebrovascular disease. It should not be used in patients with severe cardiac or vascular disorders whose condition would be expected to deteriorate if they experienced clinically important increases in blood pressure or heart rate. Although the role of atomoxetine in these cases is unknown, consideration should be given to not treating patients with clinically significant cardiac abnormalities. Patients who develop symptoms such as exertional chest pain, unexplained syncope, or other symptoms suggestive of cardiac disease during atomoxetine treatment should undergo a prompt cardiac evaluation.

    Metabolism

    Atomoxetine undergoes biotransformation primarily through the cytochrome P450 2D6 (CYP2D6) enzymatic pathway. People with reduced activity in the CYP2D6 pathway (also known as poor metabolizers or PMs) have higher plasma concentrations of atomoxetine compared with people with normal activity (also known as extensive metabolizers, or EMs). For PMs, the AUC of atomoxetine at steady-state is approximately 10-fold higher and Cmax is about 5-fold greater than for EMs. The major oxidative metabolite formed regardless of CYP2D6 status is 4-hydroxy-atomoxetine, which is rapidly glucuronidated. 4-Hydroxyatomoxetine is equipotent to atomoxetine as an inhibitor of the norepinephrine transporter, but circulates in plasma at much lower concentrations (1% of atomoxetine concentration in EMs and 0.1% of atomoxetine concentration in PMs). In individuals that lack CYP2D6 activity, 4-hydroxyatomoxetine is still the primary metabolite, but is formed by several other cytochrome P450 enzymes and at a slower rate. Another minor metabolite, N-Desmethyl-atomoxetine is formed by CYP2C19 and other cytochrome P450 enzymes, but has much less pharmacological activity than atomoxetine and lower plasma concentrations (5% of atomoxetine concentration in EMs and 45% of atomoxetine concentration in PMs).

    Absorption

    The pharmacokinetic profile of atomoxetine is highly dependent on cytochrome P450 2D6 genetic polymorphisms of the individual. A large fraction of the population (up to 10% of Caucasians and 2% of people of African descent and 1% of Asians) are poor metabolizers (PMs) of CYP2D6 metabolized drugs. These individuals have reduced activity in this pathway resulting in 10-fold higher AUCs, 5-fold higher peak plasma concentrations, and slower elimination (plasma half-life of 21.6 hours) of atomoxetine compared with people with normal CYP2D6 activity. Atomoxetine is rapidly absorbed after oral administration, with absolute bioavailability of about 63% in extensive metabolizers (EMs) and 94% in poor metabolizers (PMs). Mean maximal plasma concentrations (Cmax) are reached approximately 1 to 2 hours after dosing with a maximal concentration of 350 ng/ml with an AUC of 2 mcg.h/ml.

    Toxicity

    There is limited clinical trial experience with atomoxetine overdose. During postmarketing, there have been fatalities reported involving a mixed ingestion overdose of atomoxetine capsules and at least one other drug. There have been no reports of death involving overdose of atomoxetine capsules alone, including intentional overdoses at amounts up to 1400 mg. In some cases of overdose involving atomoxetine, seizures have been reported. The most commonly reported symptoms accompanying acute and chronic overdoses of atomoxetine capsules were gastrointestinal symptoms, somnolence, dizziness, tremor, and abnormal behavior. Hyperactivity and agitation have also been reported. Signs and symptoms consistent with mild to moderate sympathetic nervous system activation (e.g., tachycardia, blood pressure increased, mydriasis, dry mouth) have also been observed. Most events were mild to moderate. Less commonly, there have been reports of QT prolongation and mental changes, including disorientation and hallucinations. If symptoms of overdose are suspected, a Certified Poison Control Center should be consulted for up to date guidance and advice. Because atomoxetine is highly protein-bound, dialysis is not likely to be useful in the treatment of overdose.

    Indication

    Atomoxetine is indicated for the treatment of attention deficit hyperactivity disorder (ADHD) in children and adults.

    Half-life

    The reported half-life depends on the CYP2D6 genetic polymorphisms of the individual and can range from 3 to 5.6 hours.

    Protein Binding

    At therapeutic concentrations, 98.7% of plasma atomoxetine is bound to protein, with 97.5% of that being bound to albumin, followed by alpha-1-acid glycoprotein and immunoglobulin G.

    Elimination

    Atomoxetine is excreted primarily as 4-hydroxyatomoxetine-O-glucuronide, mainly in the urine (greater than 80% of the dose) and to a lesser extent in the feces (less than 17% of the dose). Only a small fraction (less than 3%) of the atomoxetine dose is excreted as unchanged atomoxetine, indicating extensive biotransformation.

    Volume of Distribution

    The reported volume of distribution of oral atomoxetine was 1.6-2.6 L/kg. The steady-state volume of distribution of intravenous atomoxetine was approximately 0.85 L/kg.

    Clearance

    The clearance rate of atomoxetine depends the CYP2D6 genetic polymorphisms of the individual and can range of 0.27-0.67 L.h/kg.

    Effect Profile

    Curated + 35 Reports
    Stimulant 7.2

    Strong stimulation and anxiety/jitters with moderate euphoria and focus

    Stimulation / Energy×3
    106.7
    Euphoria / Mood Lift×2
    73.0
    Focus / Productivity×2
    710
    Anxiety / Jitters×1
    1010
    Catalog Erowid

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 10d Baseline ~18d

    Experience Report Analysis

    Erowid
    35 Reports
    2002–2025 Date Range
    13 With Age Data
    19 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid

    Effects aggregated from 35 experience reports (35 Erowid)

    35 Reports
    19 Effects Detected
    8 Positive
    6 Adverse
    5 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 8

    Focus Enhancement 51.4% 70%
    Stimulation 40.0% 70%
    Euphoria 20.0% 70%
    Empathy 17.1% 70%
    Body High 14.3% 70%
    Tactile Enhancement 11.4% 70%
    Color Enhancement 8.6% 70%
    Music Enhancement 8.6% 70%

    Adverse Effects 6

    Anxiety 45.7% 70%
    Nausea 28.6% 70%
    Headache 20.0% 70%
    Sweating 11.4% 70%
    Increased Heart Rate 8.6% 70%
    Jaw Clenching 8.6% 70%

    Dose-Response Correlation

    How effect frequency changes across dose levels

    View data table
    Effect Strong (n=12)
    Anxiety 58.3%
    Focus Enhancement 50.0%
    Sedation 50.0%
    Stimulation 50.0%
    Nausea 33.3%
    Headache 16.7%
    Auditory Effects 16.7%
    Color Enhancement 16.7%
    Euphoria 16.7%
    Hospital 16.7%
    Sweating 16.7%
    Empathy 16.7%
    Dissociation 16.7%
    Body High 16.7%

    Dose–Effect Mapping

    Experience Reports

    How reported effects shift across dose tiers, based on 35 experience reports.

    Limited tier coverage — most reports fall within the Strong range. Effects at other dose levels may not be represented.

    Oral dose range: 40.0–80.0 mg (median 40.0 mg)
    Effect Strong (n=12)
    anxiety
    58%
    focus enhancement
    50%
    sedation
    50%
    stimulation
    50%
    nausea
    33%
    headache
    17%
    auditory effects
    17%
    color enhancement
    17%
    euphoria
    17%
    hospital
    17%
    sweating
    17%
    empathy
    17%
    dissociation
    17%
    body high
    17%

    Dosage Distribution

    Dose distribution from experience reports

    Median: 40.0 mg IQR: 40.0–80.0 mg n=23

    Real-World Dose Distribution

    62K Doses

    From 43 individual dose entries

    Oral (n=37)

    Median: 40.0mg 25th: 40.0mg 75th: 80.0mg 90th: 148.0mg
    mg/kg median: 0.678 mg/kg 75th: 1.08

    Common Combinations

    Most co-occurring substances in experience reports

    Form / Preparation

    Most common forms and preparations reported

    Body-Weight Dosing

    Dose relative to body weight from reports with weight data

    Median: 0.551 mg/kg IQR: 0.424–0.86 mg/kg n=23

    Redose Patterns

    Redosing behavior across 28 reports

    10.7% Redosed
    1.1 Avg Doses
    45m Median Interval
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