U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ATOMOXETINE HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment: # Eli Lilly

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STRATTERA

Approved Use

Attention-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 Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
414.82 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2693.29 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.64 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
ATOMOXETINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
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)
Quetiapine(9 mg)
Sources:
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)
Malaise (1 patient)
Anorexia (1 patient)
Sources:
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)
Tachycardia (6 patients)
Nausea (3 patients)
Hypertension (2 patients)
Vomiting (2 patients)
Seizure (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Tachycardia 1 patient
Disc. AE
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
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)
Quetiapine(9 mg)
Sources:
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

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no (co-administration study)
Comment: coadministration with desipramine did not alter the PK of desipramine
Page: 11, 28, 30
no
no (co-administration study)
Comment: coadministration with midazolam increased AUC by 15%
Page: 11, 28, 30
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: coadministration with paroxetine or fluoxetine increased atomoxetine steady-state plasma concentrations
Page: 8, 11, 22
unlikely
weak
weak
weak
weak
weak
weak
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2002 Dec
Atomoxetine and methylphenidate treatment in children with ADHD: a prospective, randomized, open-label trial.
2002 Jul
Once-daily atomoxetine treatment for children and adolescents with attention deficit hyperactivity disorder: a randomized, placebo-controlled study.
2002 Nov
Neurotransmission of cognition, part 2. Selective NRIs are smart drugs: exploiting regionally selective actions on both dopamine and norepinephrine to enhance cognition.
2003 Feb
Disposition and metabolic fate of atomoxetine hydrochloride: pharmacokinetics, metabolism, and excretion in the Fischer 344 rat and beagle dog.
2003 Jan
Atomoxetine: a selective noradrenaline reuptake inhibitor for the treatment of attention-deficit/hyperactivity disorder.
2003 Jul
Gateways to clinical trials.
2003 May
Atomoxetine for attention deficit/hyperactivity disorder.
2003 May
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
Involvement of norepinephrine in the control of activity and attentive processes in animal models of attention deficit hyperactivity disorder.
2004
ADHD treatment across the life cycle.
2004
Atomoxetine: a review of its use in adults with attention deficit hyperactivity disorder.
2004
Improvement in health-related quality of life in children with ADHD: an analysis of placebo controlled studies of atomoxetine.
2004 Aug
Atomoxetine (Strattera) revisited.
2004 Aug 16
[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 options in the pharmacological management of attention-deficit/hyperactivity disorder.
2004 Jul
Attention-deficit/hyperactivity disorder: medication treatment-dosing and duration of action.
2004 Jul
Acute oxcarbazepine and atomoxetine overdose with quetiapine.
2004 Jun
Pharmacological management of attention-deficit hyperactivity disorder.
2004 Jun
Evidence-based pharmacotherapy for attention-deficit hyperactivity disorder.
2004 Mar
[Attention-deficit/hyperactivity disorder (ADHS) in adulthood].
2004 Mar-Apr
Atomoxetine--treatment of attention deficit hyperactivity disorder: beyond stimulants.
2004 May
Atomoxetine hydrochloride.
2004 May
Potential noradrenergic targets for cognitive enhancement in schizophrenia.
2004 May
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
Management of hyperactivity and other acting-out problems in patients with autism spectrum disorder.
2004 Sep
Gateways to clinical trials.
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
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
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.
Name Type Language
ATOMOXETINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN  
Official Name English
NSC-759104
Code English
ATOMOXETINE HCL [VANDF]
Common Name English
(-)-N-METHYL-3-PHENYL-3-(O-TOLYLOXY)PROPYLAMINE HYDROCHLORIDE
Systematic Name English
ATOMOXETINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
ATOMOXETINE HCL
VANDF  
Common Name English
ATOMOXETINE HYDROCHLORIDE [USP-RS]
Common Name English
ATOMOXETINE HYDROCHLORIDE [JAN]
Common Name English
LY-139603
Code English
ATOMOXETINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
ATOMOXETINE (AS HYDROCHLORIDE)
Common Name English
TOMOXETINE HYDROCHLORIDE
Common Name English
Atomoxetine hydrochloride [WHO-DD]
Common Name English
ATOMOXETINE HYDROCHLORIDE [MI]
Common Name English
STRATTERA
Brand Name English
ATOMOXETINE HYDROCHLORIDE [MART.]
Common Name English
ATOMOXETINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(2-METHYLPHENOXY)-, HYDROCHLORIDE, (-)
Common Name English
ATOMOXETINE HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 173003
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
NCI_THESAURUS C265
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Code System Code Type Description
DAILYMED
57WVB6I2W0
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PRIMARY
RXCUI
353103
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PRIMARY RxNorm
CHEBI
331697
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PRIMARY
CAS
82248-59-7
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PRIMARY
NCI_THESAURUS
C47405
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PRIMARY
EVMPD
SUB75495
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PRIMARY
MERCK INDEX
m2124
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PRIMARY Merck Index
NSC
759104
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PRIMARY
ChEMBL
CHEMBL641
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PRIMARY
FDA UNII
57WVB6I2W0
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PRIMARY
EPA CompTox
DTXSID2044266
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PRIMARY
DRUG BANK
DB00289
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PRIMARY
RS_ITEM_NUM
1044469
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PRIMARY
SMS_ID
100000137397
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PRIMARY
USAN
T-123
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PRIMARY
PUBCHEM
54840
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PRIMARY