Atomoxetine hydrochloride

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 Search

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21411_strattera_lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Norepinephrine transporter 197 Target ID: CHEMBL222 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21411_strattera_lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/12431845 \| https://www.ncbi.nlm.nih.gov/pubmed/23933039	Inhibitor 8504	5.0 nM [Ki]
Serotonin transporter 183 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12431845 \| https://www.ncbi.nlm.nih.gov/pubmed/23933039	Inhibitor 8504	77.0 nM [Ki]
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12431845	Inhibitor 8504	1451.0 nM [Ki]
Glutamate receptor ionotropic, NMDA 2A 3 Target ID: Q00959 Gene ID: 24409.0 Gene Symbol: Grin2a Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20423340	Antagonist 2849	1.58 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Attention deficit hyperactivity disorder 70 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21411_strattera_lbl.pdf	Primary		Approved 8583	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

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021411s035lbl.pdf			ATOMOXETINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	inhibitor 2438 inducer 440 substrate 1193	substrate 1388 inhibitor 2507 inducer 109	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153	P-gp 2052 CYP2C19 1119 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2E1 729	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP2D6 2546	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 30	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 28, 30	no	no (co-administration study) Comment: coadministration with desipramine did not alter the PK of desipramine Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 28, 30
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 28, 30	no	no (co-administration study) Comment: coadministration with midazolam increased AUC by 15% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 11, 28, 30

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 8, 11, 22	major	yes (co-administration study) Comment: coadministration with paroxetine or fluoxetine increased atomoxetine steady-state plasma concentrations Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 8, 11, 22
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17963743/	unlikely
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	weak
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_biopharmr_P1.pdf Page: 22.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-411_Strattera_pharmr_P1.pdf Page: 15.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:127342	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:127342
ChemicalBook	CB3378328	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3378328
eMolecules	1883572	https://www.emolecules.com/cgi-bin/more?vid=1883572
MolPort	MolPort-002-052-062	https://www.molport.com/shop/molecule-link/MolPort-002-052-062
ZINC	ZINC000001842633	http://zinc15.docking.org/substances/ZINC000001842633

PubMed

Title	Date	PubMed
Drug development process for a product with a primary pediatric indication.	2002	12562061
Drugs under investigation for attention-deficit hyperactivity disorder.	2002 Aug	12211416
Castration increases nisoxetine-evoked norepinephrine levels in vivo within the olfactory bulb of male rats.	2002 Aug 9	12133560
Gateways to clinical trials.	2002 Dec	12616965
Gateways to clinical trials.	2002 Nov	12616707
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	12431845
Effect of potent CYP2D6 inhibition by paroxetine on atomoxetine pharmacokinetics.	2002 Nov	12412820
Cardiovascular effects of atomoxetine in children, adolescents, and adults.	2003	12862507
Atomoxetine.	2003	12765489
Pharmacological treatments for ADHD and the novel agent atomoxetine.	2003 Aug	13677007
Atomoxetine and pregnancy.	2003 Aug	12874488
Disposition and metabolic fate of atomoxetine hydrochloride: pharmacokinetics, metabolism, and excretion in the Fischer 344 rat and beagle dog.	2003 Jan	12485957
Atomoxetine in adults with ADHD: two randomized, placebo-controlled studies.	2003 Jan 15	12547466
Atomoxetine: a selective noradrenaline reuptake inhibitor for the treatment of attention-deficit/hyperactivity disorder.	2003 Jul	12831341
Gateways to clinical trials.	2003 May	12808477
Atomoxetine for attention deficit/hyperactivity disorder.	2003 May	12751480
The use of antidepressants to treat attention deficit hyperactivity disorder in adults.	2003 Sep	14513926
Enhanced attention in rhesus monkeys as a common factor for the cognitive effects of drugs with abuse potential.	2003 Sep	12768267
Atomoxetine pharmacokinetics in children and adolescents with attention deficit hyperactivity disorder.	2003 Spring	12804126
Spotlight on atomoxetine in adults with attention-deficit hyperactivity disorder.	2004	15089111
Impact of ADHD and its treatment on substance abuse in adults.	2004	15046534
ADHD treatment across the life cycle.	2004	15046532
A prospective, multicenter, open-label assessment of atomoxetine in non-North American children and adolescents with ADHD.	2004 Aug	15365896
Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies.	2004 Aug	15363606
[Tourette syndrome: an analysis of its comorbidity and specific treatment].	2004 Feb	15011166
[New therapeutic options in the treatment of attention deficit/hyperactivity disorder].	2004 Feb	15011165
New drugs 04, part 1.	2004 Feb	14758333
Gateways to clinical trials.	2004 Jan-Feb	14988742
The use of atomoxetine adjunctively in fibromyalgia syndrome.	2004 Jul	15362262
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	15231966
Relapse prevention in pediatric patients with ADHD treated with atomoxetine: a randomized, double-blind, placebo-controlled study.	2004 Jul	15213591
The link between health-related quality of life and clinical symptoms among children with attention-deficit hyperactivity disorder.	2004 Jun	15194901
Acute oxcarbazepine and atomoxetine overdose with quetiapine.	2004 Jun	15171487
Pharmacological management of attention-deficit hyperactivity disorder.	2004 Jun	15163276
Nonstimulant treatment of adult attention-deficit/hyperactivity disorder.	2004 Jun	15064003
Driving impairments in teens and adults with attention-deficit/hyperactivity disorder.	2004 Jun	15063996
New drugs of 2003.	2004 Mar-Apr	15098851
[Attention-deficit/hyperactivity disorder (ADHS) in adulthood].	2004 Mar-Apr	15037976
Atomoxetine hydrochloride.	2004 May	15152632
Potential noradrenergic targets for cognitive enhancement in schizophrenia.	2004 May	15115947
Adrenergic alpha 2C receptor genomic organization: association study in adult ADHD.	2004 May 15	15108182
New drugs for the treatment of attention-deficit/hyperactivity disorder.	2004 Nov	15571486
Combining stimulants with monoamine oxidase inhibitors: a review of uses and one possible additional indication.	2004 Nov	15554766
Atomoxetine: the first nonstimulant for the management of attention-deficit/hyperactivity disorder.	2004 Nov 15	15581262
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	15496372
[Atomoxetine for the treatment of attention-deficit/hyperactivity disorder].	2004 Oct	15472782
Management of hyperactivity and other acting-out problems in patients with autism spectrum disorder.	2004 Sep	15575418
Gateways to clinical trials.	2004 Sep	15538546
Atomoxetine and stimulants in combination for treatment of attention deficit hyperactivity disorder: four case reports.	2004 Spring	15142400
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	15526000

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

In Vitro Use Guide

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

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Name

Type

Language

Atomoxetine hydrochloride

Official Name

English

Atomoxetine HCL

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