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

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

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

1.03826883E12
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:00:43 UTC 2022
Edited
by admin
on Fri Dec 16 16:00:43 UTC 2022
Record UNII
57WVB6I2W0
Record Status Validated (UNII)
Record Version
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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 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
NCI_THESAURUS C265
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
Code System Code Type Description
DAILYMED
57WVB6I2W0
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
RXCUI
353103
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY RxNorm
CHEBI
331697
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
CAS
82248-59-7
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
NCI_THESAURUS
C47405
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
EVMPD
SUB75495
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
MERCK INDEX
M2124
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY Merck Index
NSC
759104
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
ChEMBL
CHEMBL641
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
FDA UNII
57WVB6I2W0
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
EPA CompTox
DTXSID2044266
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
DRUG BANK
DB00289
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
RS_ITEM_NUM
1044469
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
USAN
T-123
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
PUBCHEM
54840
Created by admin on Fri Dec 16 16:00:43 UTC 2022 , Edited by admin on Fri Dec 16 16:00:43 UTC 2022
PRIMARY
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