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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=CC=CC=C1C)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 ( - )

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

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
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
Drug development process for a product with a primary pediatric indication.
2002
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
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
Effect of potent CYP2D6 inhibition by paroxetine on atomoxetine pharmacokinetics.
2002 Nov
Cardiovascular effects of atomoxetine in children, adolescents, and adults.
2003
Atomoxetine.
2003
Pharmacological treatments for ADHD and the novel agent atomoxetine.
2003 Aug
Atomoxetine and pregnancy.
2003 Aug
Disposition and metabolic fate of atomoxetine hydrochloride: pharmacokinetics, metabolism, and excretion in the Fischer 344 rat and beagle dog.
2003 Jan
Atomoxetine in adults with ADHD: two randomized, placebo-controlled studies.
2003 Jan 15
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
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
Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies.
2004 Aug
[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
Gateways to clinical trials.
2004 Jan-Feb
The use of atomoxetine adjunctively in fibromyalgia syndrome.
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
New drugs of 2003.
2004 Mar-Apr
[Attention-deficit/hyperactivity disorder (ADHS) in adulthood].
2004 Mar-Apr
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
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
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 Mon Mar 31 17:36:36 GMT 2025
Edited
by admin
on Mon Mar 31 17:36:36 GMT 2025
Record UNII
57WVB6I2W0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Atomoxetine hydrochloride
JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN  
Official Name English
Atomoxetine HCL
VANDF  
Preferred 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 hydrochloride [USP-RS]
Common Name English
Atomoxetine hydrochloride [JAN]
Common Name English
(R)-N-Methyl-3-(2-methylphenoxy)-3-phenylpropylamine hydrochloride
Systematic Name English
(R)-(-)-N-Methyl-3-[(2-methylphenyl)oxy]-3-phenyl-1-aminopropane hydrochloride
Systematic 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
(R)-(-)-Tomoxetine hydrochloride
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 Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
NCI_THESAURUS C265
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
Code System Code Type Description
DAILYMED
57WVB6I2W0
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
RXCUI
353103
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY RxNorm
CHEBI
331697
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
CAS
82248-59-7
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
NCI_THESAURUS
C47405
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
EVMPD
SUB75495
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
MERCK INDEX
m2124
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY Merck Index
NSC
759104
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
ChEMBL
CHEMBL641
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
FDA UNII
57WVB6I2W0
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID2044266
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
DRUG BANK
DB00289
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
RS_ITEM_NUM
1044469
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
SMS_ID
100000137397
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
USAN
T-123
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
PUBCHEM
54840
Created by admin on Mon Mar 31 17:36:36 GMT 2025 , Edited by admin on Mon Mar 31 17:36:36 GMT 2025
PRIMARY
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