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 Date2002 |
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 |
---|---|---|
An open-label, dose-ranging study of atomoxetine in children with attention deficit hyperactivity disorder. | 2001 Fall |
|
Atomoxetine in the treatment of children and adolescents with attention-deficit/hyperactivity disorder: a randomized, placebo-controlled, dose-response study. | 2001 Nov |
|
The norepinephrine transporter gene and attention-deficit hyperactivity disorder. | 2002 Apr 8 |
|
Drugs under investigation for attention-deficit hyperactivity disorder. | 2002 Aug |
|
Castration increases nisoxetine-evoked norepinephrine levels in vivo within the olfactory bulb of male rats. | 2002 Aug 9 |
|
Gateways to clinical trials. | 2002 Dec |
|
Atomoxetine and methylphenidate treatment in children with ADHD: a prospective, randomized, open-label trial. | 2002 Jul |
|
Identification of the human cytochromes P450 responsible for atomoxetine metabolism. | 2002 Mar |
|
Gateways to clinical trials. | 2002 Nov |
|
Atomoxetine increases extracellular levels of norepinephrine and dopamine in prefrontal cortex of rat: a potential mechanism for efficacy in attention deficit/hyperactivity disorder. | 2002 Nov |
|
Brain circuits determine destiny in depression: a novel approach to the psychopharmacology of wakefulness, fatigue, and executive dysfunction in major depressive disorder. | 2003 |
|
Cardiovascular effects of atomoxetine in children, adolescents, and adults. | 2003 |
|
Updates on attention deficit hyperactivity disorder, child abuse and neglect, and sudden infant death syndrome. | 2003 Apr |
|
Atomoxetine and pregnancy. | 2003 Aug |
|
Atomoxetine hydrochloride for the treatment of attention-deficit/hyperactivity disorder. | 2003 Dec |
|
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 |
|
Disposition and metabolic fate of atomoxetine hydrochloride: pharmacokinetics, metabolism, and excretion in the Fischer 344 rat and beagle dog. | 2003 Jan |
|
Effect of hepatic impairment on the pharmacokinetics of atomoxetine and its metabolites. | 2003 Mar |
|
Strattera approved to treat ADHD. | 2003 Mar-Apr |
|
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 |
|
Non-stimulant medications in the treatment of ADHD. | 2004 |
|
A prospective, multicenter, open-label assessment of atomoxetine in non-North American children and adolescents with ADHD. | 2004 Aug |
|
Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies. | 2004 Aug |
|
Synthesis and biological evaluation of the major metabolite of atomoxetine: elucidation of a partial kappa-opioid agonist effect. | 2004 Aug 2 |
|
Changes in symptoms and adverse events after discontinuation of atomoxetine in children and adults with attention deficit/hyperactivity disorder: a prospective, placebo-controlled assessment. | 2004 Feb |
|
Atomoxetine treatment of attention-deficit/hyperactivity disorder. | 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 |
|
Potential noradrenergic targets for cognitive enhancement in schizophrenia. | 2004 May |
|
New drugs for the treatment of attention-deficit/hyperactivity disorder. | 2004 Nov |
|
Atomoxetine: the first nonstimulant for the management of attention-deficit/hyperactivity disorder. | 2004 Nov 15 |
|
Management of hyperactivity and other acting-out problems in patients with autism spectrum disorder. | 2004 Sep |
|
Gateways to clinical trials. | 2004 Sep |
|
Atomoxetine and nonresponders to stimulants. | 2004 Sep |
|
Atomoxetine and tics in ADHD. | 2004 Sep |
|
Evaluation of the reinforcing effects of monoamine reuptake inhibitors under a concurrent schedule of food and i.v. drug delivery in rhesus monkeys. | 2005 Apr |
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 15 15:02:50 GMT 2023
by
admin
on
Fri Dec 15 15:02:50 GMT 2023
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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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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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100000137397
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T-123
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54840
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