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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO
Molecular Weight 255.3554
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATOMOXETINE

SMILES

Cc1ccccc1O[C@]([H])(CCNC)c2ccccc2

InChI

InChIKey=VHGCDTVCOLNTBX-QGZVFWFLSA-N
InChI=1S/C17H21NO/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/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H21NO
Molecular Weight 255.3554
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

1038268800000
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
Health Status: unhealthy
Age Group: 12 years
Sex: M
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
Health Status: unhealthy
Age Group: 14 years
Sex: F
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
Health Status: healthy
Age Group: 17 years
Sex: F
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
Sources:
unknown, 19 years
Health Status: unknown
Age Group: 19 years
Sex: M
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
Sources:
unhealthy, 26 years
Health Status: unhealthy
Age Group: 26 years
Sex: F
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
Health Status: unhealthy
Age Group: 5 - 6 years
Sex: M+F
Sources:
120 mg 1 times / day steady, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: steady
Dose: 120 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
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
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
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
Health Status: unhealthy
Age Group: 12 years
Sex: M
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
Health Status: unhealthy
Age Group: 14 years
Sex: F
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
Health Status: healthy
Age Group: 17 years
Sex: F
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
Sources:
unknown, 19 years
Health Status: unknown
Age Group: 19 years
Sex: M
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
Sources:
unhealthy, 26 years
Health Status: unhealthy
Age Group: 26 years
Sex: F
Sources:
Anorexia 1 patient
Disc. AE
120 mg 1 times / day steady, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: steady
Dose: 120 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Malaise 1 patient
Disc. AE
120 mg 1 times / day steady, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: steady
Dose: 120 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nausea 1 patient
Disc. AE
120 mg 1 times / day steady, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: steady
Dose: 120 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Seizure 1 patient
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
Drowsiness 10 patients
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
Hypertension 2 patients
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
Vomiting 2 patients
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
Nausea 3 patients
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
Tachycardia 6 patients
249 mg 1 times / day steady, oral
Highest studied dose
Dose: 249 mg, 1 times / day
Route: oral
Route: steady
Dose: 249 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
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

Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Atomoxetine hydrochloride for the treatment of attention-deficit/hyperactivity disorder.
2003 Dec
Non-stimulant medications in the treatment of ADHD.
2004
Involvement of norepinephrine in the control of activity and attentive processes in animal models of attention deficit hyperactivity disorder.
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
Atomoxetine: a review of its use in adults with attention deficit hyperactivity disorder.
2004
Seizures and prolonged QTc with atomoxetine overdose.
2004 Apr
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
Atomoxetine, a novel treatment for attention-deficit-hyperactivity disorder.
2004 Aug
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
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 treatment of attention-deficit/hyperactivity disorder.
2004 Jan
Gateways to clinical trials.
2004 Jan-Feb
The use of atomoxetine adjunctively in fibromyalgia syndrome.
2004 Jul
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
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
Nonstimulant treatment of adult attention-deficit/hyperactivity disorder.
2004 Jun
Driving impairments in teens and adults with attention-deficit/hyperactivity disorder.
2004 Jun
Evidence-based pharmacotherapy for attention-deficit hyperactivity disorder.
2004 Mar
New drugs of 2003.
2004 Mar-Apr
[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
Adrenergic alpha 2C receptor genomic organization: association study in adult ADHD.
2004 May 15
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
Gateways to clinical trials.
2004 Sep
Aggression, mania, and hypomania induction associated with atomoxetine.
2004 Sep
Atomoxetine and nonresponders to stimulants.
2004 Sep
Atomoxetine and tics in ADHD.
2004 Sep
Evaluation of the reinforcing effects of atomoxetine in monkeys: comparison to methylphenidate and desipramine.
2004 Sep 6
Atomoxetine and stimulants in combination for treatment of attention deficit hyperactivity disorder: four case reports.
2004 Spring
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
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 Sat Jun 26 01:42:52 UTC 2021
Edited
by admin
on Sat Jun 26 01:42:52 UTC 2021
Record UNII
ASW034S0B8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATOMOXETINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ATOMOXETINE [WHO-DD]
Common Name English
ATOMOXETINE [INN]
Common Name English
ATOMOXETINE [VANDF]
Common Name English
ATOMOXETINE [MI]
Common Name English
ATOMOXETINE [HSDB]
Common Name English
Classification Tree Code System Code
WHO-ATC N06BA09
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
LIVERTOX 71
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
WHO-VATC QN06BA09
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
NCI_THESAURUS C265
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
NDF-RT N0000175695
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
NDF-RT N0000000102
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
Code System Code Type Description
PUBCHEM
54841
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
NCI_THESAURUS
C74141
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
CAS
83015-26-3
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
HSDB
7352
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
EVMPD
SUB20597
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
RXCUI
38400
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY RxNorm
FDA UNII
ASW034S0B8
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
IUPHAR
7118
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
LACTMED
Atomoxetine
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL641
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
WIKIPEDIA
ATOMOXETINE
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
DRUG BANK
DB00289
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
MERCK INDEX
M2124
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY Merck Index
MESH
C041930
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
DRUG CENTRAL
256
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
INN
5354
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
EPA CompTox
83015-26-3
Created by admin on Sat Jun 26 01:42:53 UTC 2021 , Edited by admin on Sat Jun 26 01:42:53 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
FECAL; URINE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
POTENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MAJOR
METABOLITE LESS ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC