Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H21NO.ClH |
Molecular Weight | 291.816 |
Optical Activity | ( - ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNCC[C@@H](OC1=C(C)C=CC=C1)C2=CC=CC=C2
InChI
InChIKey=LUCXVPAZUDVVBT-UNTBIKODSA-N
InChI=1S/C17H21NO.ClH/c1-14-8-6-7-11-16(14)19-17(12-13-18-2)15-9-4-3-5-10-15;/h3-11,17-18H,12-13H2,1-2H3;1H/t17-;/m1./s1
Molecular Formula | C17H21NO |
Molecular Weight | 255.3547 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/atomoxetine.html
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/atomoxetine.html
Atomoxetine is indicated for the treatment of Attention-Deficit/Hyperactivity Disorder. The precise mechanism by which atomoxetine produces its therapeutic effects in Attention-Deficit/Hyperactivity Disorder (ADHD) is unknown, but is thought to be related to selective inhibition of the pre-synaptic norepinephrine transporter. Most common adverse reactions are: nausea, vomiting, fatigue, decreased appetite, abdominal pain, and somnolence, constipation, dry mouth, dizziness, erectile dysfunction, and urinary hesitation. Atomoxetine is a substrate for CYP2D6 and hence concurrent treatment with CYP2D6 inhibitors such as bupropion (Wellbutrin) or fluoxetine (Prozac) is not recommended, as this can lead to significant elevations of plasma atomoxetine levels.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800000561
Curator's Comment: # Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
5.0 nM [Ki] | |||
Target ID: CHEMBL228 |
77.0 nM [Ki] | ||
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12431845 |
1451.0 nM [Ki] | ||
Target ID: Q00959 Gene ID: 24409.0 Gene Symbol: Grin2a Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20423340 |
1.58 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | STRATTERA Approved UseAttention-Deficit/Hyperactivity Disorder (ADHD) STRATTERA is indicated for the treatment of Attention-Deficit/Hyperactivity Disorder (ADHD). The efficacy of STRATTERA Capsules was established in seven clinical trials in outpatients with ADHD: four 6 to 9-week trials in pediatric patients (ages 6 to 18), two 10-week trial in adults, and one maintenance trial in pediatrics (ages 6 to 15) [see Clinical Studies (14) Launch Date1.03826883E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
414.82 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23812961 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
ATOMOXETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2693.29 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23812961 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
ATOMOXETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.64 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23812961 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
ATOMOXETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
ATOMOXETINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
180 mg single, oral Overdose |
unhealthy, 12 years n = 1 Health Status: unhealthy Condition: mistakenly instead of dextroampheta Age Group: 12 years Sex: M Population Size: 1 Sources: |
Disc. AE: Tachycardia... AEs leading to discontinuation/dose reduction: Tachycardia (1 patient) Sources: |
480 mg 1 times / day steady, oral Highest studied dose Dose: 480 mg, 1 times / day Route: oral Route: steady Dose: 480 mg, 1 times / day Sources: |
unhealthy, 14 years n = 1 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: 14 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hypertension... AEs leading to discontinuation/dose reduction: Hypertension (1 patient) Sources: |
2840 mg single, oral Overdose Dose: 2840 mg Route: oral Route: single Dose: 2840 mg Sources: |
healthy, 17 years n = 1 Health Status: healthy Condition: attempted suicide Age Group: 17 years Sex: F Population Size: 1 Sources: |
Disc. AE: Sinus tachycardia... AEs leading to discontinuation/dose reduction: Sinus tachycardia (1 patient) Sources: |
1.2 g single, oral Overdose Dose: 1.2 g Route: oral Route: single Dose: 1.2 g Co-administed with:: oxcarbazepine(36 g) Sources: Quetiapine(9 mg) |
unknown, 19 years n = 1 Health Status: unknown Age Group: 19 years Sex: M Population Size: 1 Sources: |
Disc. AE: Depression central nervous system... AEs leading to discontinuation/dose reduction: Depression central nervous system (1 patient) Sources: |
40 mg 2 times / day steady, oral Recommended Dose: 40 mg, 2 times / day Route: oral Route: steady Dose: 40 mg, 2 times / day Co-administed with:: fluoxetine Sources: |
unhealthy, 26 years n = 1 Health Status: unhealthy Condition: temper outbursts, impulsivity, difficulty paying attention, marital discord Age Group: 26 years Sex: F Population Size: 1 Sources: |
Disc. AE: ST segment elevation myocardial infarction... AEs leading to discontinuation/dose reduction: ST segment elevation myocardial infarction (1 patient) Sources: |
1.8 mg/kg 1 times / day steady, oral Highest studied dose Dose: 1.8 mg/kg, 1 times / day Route: oral Route: steady Dose: 1.8 mg/kg, 1 times / day Sources: |
unhealthy, 5 - 6 years n = 44 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: 5 - 6 years Sex: M+F Population Size: 44 Sources: |
|
120 mg 1 times / day steady, oral (max) Studied dose Dose: 120 mg, 1 times / day Route: oral Route: steady Dose: 120 mg, 1 times / day Sources: |
unhealthy, adult n = 45 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: adult Sex: unknown Population Size: 45 Sources: |
Disc. AE: Nausea, Malaise... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Sources: Malaise (1 patient) Anorexia (1 patient) |
249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Other AEs: Drowsiness, Tachycardia... Other AEs: Drowsiness (10 patients) Sources: Tachycardia (6 patients) Nausea (3 patients) Hypertension (2 patients) Vomiting (2 patients) Seizure (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Tachycardia | 1 patient Disc. AE |
180 mg single, oral Overdose |
unhealthy, 12 years n = 1 Health Status: unhealthy Condition: mistakenly instead of dextroampheta Age Group: 12 years Sex: M Population Size: 1 Sources: |
Hypertension | 1 patient Disc. AE |
480 mg 1 times / day steady, oral Highest studied dose Dose: 480 mg, 1 times / day Route: oral Route: steady Dose: 480 mg, 1 times / day Sources: |
unhealthy, 14 years n = 1 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: 14 years Sex: F Population Size: 1 Sources: |
Sinus tachycardia | 1 patient Disc. AE |
2840 mg single, oral Overdose Dose: 2840 mg Route: oral Route: single Dose: 2840 mg Sources: |
healthy, 17 years n = 1 Health Status: healthy Condition: attempted suicide Age Group: 17 years Sex: F Population Size: 1 Sources: |
Depression central nervous system | 1 patient Disc. AE |
1.2 g single, oral Overdose Dose: 1.2 g Route: oral Route: single Dose: 1.2 g Co-administed with:: oxcarbazepine(36 g) Sources: Quetiapine(9 mg) |
unknown, 19 years n = 1 Health Status: unknown Age Group: 19 years Sex: M Population Size: 1 Sources: |
ST segment elevation myocardial infarction | 1 patient Disc. AE |
40 mg 2 times / day steady, oral Recommended Dose: 40 mg, 2 times / day Route: oral Route: steady Dose: 40 mg, 2 times / day Co-administed with:: fluoxetine Sources: |
unhealthy, 26 years n = 1 Health Status: unhealthy Condition: temper outbursts, impulsivity, difficulty paying attention, marital discord Age Group: 26 years Sex: F Population Size: 1 Sources: |
Anorexia | 1 patient Disc. AE |
120 mg 1 times / day steady, oral (max) Studied dose Dose: 120 mg, 1 times / day Route: oral Route: steady Dose: 120 mg, 1 times / day Sources: |
unhealthy, adult n = 45 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: adult Sex: unknown Population Size: 45 Sources: |
Malaise | 1 patient Disc. AE |
120 mg 1 times / day steady, oral (max) Studied dose Dose: 120 mg, 1 times / day Route: oral Route: steady Dose: 120 mg, 1 times / day Sources: |
unhealthy, adult n = 45 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: adult Sex: unknown Population Size: 45 Sources: |
Nausea | 1 patient Disc. AE |
120 mg 1 times / day steady, oral (max) Studied dose Dose: 120 mg, 1 times / day Route: oral Route: steady Dose: 120 mg, 1 times / day Sources: |
unhealthy, adult n = 45 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: adult Sex: unknown Population Size: 45 Sources: |
Seizure | 1 patient | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Drowsiness | 10 patients | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Hypertension | 2 patients | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Vomiting | 2 patients | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Nausea | 3 patients | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Tachycardia | 6 patients | 249 mg 1 times / day steady, oral (mean) Highest studied dose Dose: 249 mg, 1 times / day Route: oral Route: steady Dose: 249 mg, 1 times / day Sources: |
unhealthy, children n = 40 Health Status: unhealthy Condition: attention deficit hyperactivity disorder Age Group: children Sex: M+F Population Size: 40 Sources: |
Overview
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 15.0 |
PubMed
Title | Date | PubMed |
---|---|---|
New treatments and approaches for attention deficit hyperactivity disorder. | 2001 Apr |
|
Safety profile of atomoxetine in the treatment of children and adolescents with ADHD. | 2002 |
|
Drug development process for a product with a primary pediatric indication. | 2002 |
|
Brain circuits determine destiny in depression: a novel approach to the psychopharmacology of wakefulness, fatigue, and executive dysfunction in major depressive disorder. | 2003 |
|
Atomoxetine. | 2003 |
|
Pharmacologic treatment approaches for children and adolescents with posttraumatic stress disorder. | 2003 Apr |
|
Atomoxetine (strattera) for ADHD. | 2003 Feb 3 |
|
Disposition and metabolic fate of atomoxetine hydrochloride: the role of CYP2D6 in human disposition and metabolism. | 2003 Jan |
|
Atomoxetine: a selective noradrenaline reuptake inhibitor for the treatment of attention-deficit/hyperactivity disorder. | 2003 Jul |
|
Strattera approved to treat ADHD. | 2003 Mar-Apr |
|
Gateways to clinical trials. | 2003 May |
|
Atomoxetine for attention deficit/hyperactivity disorder. | 2003 May |
|
Atomoxetine for ADHD. | 2003 Nov 1 |
|
The use of antidepressants to treat attention deficit hyperactivity disorder in adults. | 2003 Sep |
|
Enhanced attention in rhesus monkeys as a common factor for the cognitive effects of drugs with abuse potential. | 2003 Sep |
|
Atomoxetine pharmacokinetics in children and adolescents with attention deficit hyperactivity disorder. | 2003 Spring |
|
Non-stimulant medications in the treatment of ADHD. | 2004 |
|
Spotlight on atomoxetine in adults with attention-deficit hyperactivity disorder. | 2004 |
|
Impact of ADHD and its treatment on substance abuse in adults. | 2004 |
|
ADHD treatment across the life cycle. | 2004 |
|
A prospective, multicenter, open-label assessment of atomoxetine in non-North American children and adolescents with ADHD. | 2004 Aug |
|
Atomoxetine (Strattera) revisited. | 2004 Aug 16 |
|
Synthesis and biological evaluation of the major metabolite of atomoxetine: elucidation of a partial kappa-opioid agonist effect. | 2004 Aug 2 |
|
[Tourette syndrome: an analysis of its comorbidity and specific treatment]. | 2004 Feb |
|
[New therapeutic options in the treatment of attention deficit/hyperactivity disorder]. | 2004 Feb |
|
New drugs 04, part 1. | 2004 Feb |
|
Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome. | 2004 Feb |
|
[Medical treatments of hyperactive child]. | 2004 Jan |
|
Gateways to clinical trials. | 2004 Jan-Feb |
|
Once-daily atomoxetine treatment for children with attention-deficit/hyperactivity disorder, including an assessment of evening and morning behavior: a double-blind, placebo-controlled trial. | 2004 Jul |
|
Relapse prevention in pediatric patients with ADHD treated with atomoxetine: a randomized, double-blind, placebo-controlled study. | 2004 Jul |
|
The link between health-related quality of life and clinical symptoms among children with attention-deficit hyperactivity disorder. | 2004 Jun |
|
Acute oxcarbazepine and atomoxetine overdose with quetiapine. | 2004 Jun |
|
Pharmacological management of attention-deficit hyperactivity disorder. | 2004 Jun |
|
New drugs of 2003. | 2004 Mar-Apr |
|
Atomoxetine--treatment of attention deficit hyperactivity disorder: beyond stimulants. | 2004 May |
|
Atomoxetine hydrochloride. | 2004 May |
|
New drugs for the treatment of attention-deficit/hyperactivity disorder. | 2004 Nov |
|
Combining stimulants with monoamine oxidase inhibitors: a review of uses and one possible additional indication. | 2004 Nov |
|
Atomoxetine: the first nonstimulant for the management of attention-deficit/hyperactivity disorder. | 2004 Nov 15 |
|
A lifetime of distractions. ADHD is no longer just a children's disease. Many adults are being diagnosed and treated for the condition. | 2004 Oct |
|
[Atomoxetine for the treatment of attention-deficit/hyperactivity disorder]. | 2004 Oct |
|
Mania induction associated with atomoxetine. | 2004 Oct |
|
Management of hyperactivity and other acting-out problems in patients with autism spectrum disorder. | 2004 Sep |
|
Aggression, mania, and hypomania induction associated with atomoxetine. | 2004 Sep |
|
Atomoxetine and tics in ADHD. | 2004 Sep |
|
Atomoxetine and stimulants in combination for treatment of attention deficit hyperactivity disorder: four case reports. | 2004 Spring |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/atomoxetine.html
Atomoxetine should be initiated at a total daily dose of approximately 0.5 mg/kg and increased after a minimum of 3 days to a target total daily dose of approximately 1.2 mg/kg administered either as a single daily dose in the morning or as evenly divided doses in the morning and late afternoon/early evening. No additional benefit has been demonstrated for doses higher than 1.2 mg/kg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20423340
Electrophysiological recordings was performed with the extracellular standard solution at different membrane potentials ranging from -80 mV to +40 mV while the concentration of the agonists (100 uM NMDA/10 uM glycine) and the antagonist (25 uM atomoxetine) were kept constant. The inhibitory effect was clearly voltage-dependent, so that the inhibition was attenuated by depolarization.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:00:43 UTC 2022
by
admin
on
Fri Dec 16 16:00:43 UTC 2022
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Record UNII |
57WVB6I2W0
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
173003
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NCI_THESAURUS |
C265
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57WVB6I2W0
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353103
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331697
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82248-59-7
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C47405
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SUB75495
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M2124
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759104
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CHEMBL641
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57WVB6I2W0
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DTXSID2044266
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DB00289
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1044469
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T-123
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54840
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IMPURITY -> PARENT |
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