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Details

Stereochemistry RACEMIC
Molecular Formula C17H18F3NO.ClH
Molecular Weight 345.787
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOXETINE HYDROCHLORIDE

SMILES

Cl.CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C2=CC=CC=C2

InChI

InChIKey=GIYXAJPCNFJEHY-UHFFFAOYSA-N
InChI=1S/C17H18F3NO.ClH/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20;/h2-10,16,21H,11-12H2,1H3;1H

HIDE SMILES / InChI

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

Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Fluoxetine hydrochloride is the first agent of the class of antidepressants known as selective serotonin-reuptake inhibitors (SSRIs). Fluoxetine is a racemic mixture of the R- and S- enantiomers and are of equivalent pharmacologic activity. Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Fluoxetine is marketed under the trade names Prozac and Sarafem among others. It is also marketed for the treatment of premenstrual dysphoric disorder (Sarafem®, fluoxetine hydrochloride). PROZAC is a selective serotonin reuptake inhibitor indicated for: • Acute and maintenance treatment of Major Depressive Disorder (MDD) in adult and pediatric patients aged 8 to 18 years • Acute and maintenance treatment of Obsessive Compulsive Disorder (OCD) in adult and pediatric patients aged 7 to 17 years • Acute and maintenance treatment of Bulimia Nervosa in adult patients • Acute treatment of Panic Disorder, with or without agoraphobia, in adult patients. Studies at clinically relevant doses in man have demonstrated that fluoxetine blocks the uptake of serotonin into human platelets. Studies in animals also suggest that fluoxetine is a much more potent uptake inhibitor of serotonin than of norepinephrine. Antagonism of muscarinic, histaminergic, and α1-adrenergic receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects of classical tricyclic antidepressant (TCA) drugs. Fluoxetine binds to these and other membrane receptors from brain tissue much less potently in vitro than do the tricyclic drugs.

Originator

Curator's Comment: # Eli Lilly

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROZAC

Approved Use

Fluoxetine is a selective serotonin reuptake inhibitor indicated for: Acute and maintenance treatment of Major Depressive Disorder (MDD) in adult and pediatric patients aged 8 to 18 years (1.1) Acute and maintenance treatment of Obsessive Compulsive Disorder (OCD) in adult and pediatric patients aged 7 to 17 years (1.2) Acute and maintenance treatment of Bulimia Nervosa in adult patients (1.3) Acute treatment of Panic Disorder, with or without agoraphobia, in adult patients (1.4) Fluoxetine and olanzapine in combination for: Acute treatment of Depressive Episodes Associated with Bipolar I Disorder in adults (1.5) 1.1 Major Depressive Disorder Fluoxetine hydrochloride is indicated for the acute and maintenance treatment of Major Depressive Disorder in adult patients and in pediatric patients aged 8 to18 years [see CLINICAL STUDIES (14.1)

Launch Date

1987
Primary
PROZAC

Approved Use

Fluoxetine is a selective serotonin reuptake inhibitor indicated for: Acute and maintenance treatment of Major Depressive Disorder (MDD) in adult and pediatric patients aged 8 to 18 years (1.1) Acute and maintenance treatment of Obsessive Compulsive Disorder (OCD) in adult and pediatric patients aged 7 to 17 years (1.2) Acute and maintenance treatment of Bulimia Nervosa in adult patients (1.3) Acute treatment of Panic Disorder, with or without agoraphobia, in adult patients (1.4) Fluoxetine and olanzapine in combination for: Acute treatment of Depressive Episodes Associated with Bipolar I Disorder in adults (1.5) 1.1 Major Depressive Disorder Fluoxetine hydrochloride is indicated for the acute and maintenance treatment of Major Depressive Disorder in adult patients and in pediatric patients aged 8 to18 years [see CLINICAL STUDIES (14.1)

Launch Date

1987
Primary
PROZAC

Approved Use

Fluoxetine is a selective serotonin reuptake inhibitor indicated for: Acute and maintenance treatment of Major Depressive Disorder (MDD) in adult and pediatric patients aged 8 to 18 years (1.1) Acute and maintenance treatment of Obsessive Compulsive Disorder (OCD) in adult and pediatric patients aged 7 to 17 years (1.2) Acute and maintenance treatment of Bulimia Nervosa in adult patients (1.3) Acute treatment of Panic Disorder, with or without agoraphobia, in adult patients (1.4) Fluoxetine and olanzapine in combination for: Acute treatment of Depressive Episodes Associated with Bipolar I Disorder in adults (1.5) 1.1 Major Depressive Disorder Fluoxetine hydrochloride is indicated for the acute and maintenance treatment of Major Depressive Disorder in adult patients and in pediatric patients aged 8 to18 years [see CLINICAL STUDIES (14.1)

Launch Date

1987
Primary
PROZAC

Approved Use

Fluoxetine is a selective serotonin reuptake inhibitor indicated for: Acute and maintenance treatment of Major Depressive Disorder (MDD) in adult and pediatric patients aged 8 to 18 years (1.1) Acute and maintenance treatment of Obsessive Compulsive Disorder (OCD) in adult and pediatric patients aged 7 to 17 years (1.2) Acute and maintenance treatment of Bulimia Nervosa in adult patients (1.3) Acute treatment of Panic Disorder, with or without agoraphobia, in adult patients (1.4) Fluoxetine and olanzapine in combination for: Acute treatment of Depressive Episodes Associated with Bipolar I Disorder in adults (1.5) 1.1 Major Depressive Disorder Fluoxetine hydrochloride is indicated for the acute and maintenance treatment of Major Depressive Disorder in adult patients and in pediatric patients aged 8 to18 years [see CLINICAL STUDIES (14.1)

Launch Date

1987
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22.56 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13576.38 pg/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1101.46 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
788626.72 pg × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
46.39 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
49.7 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUOXETINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5.5%
FLUOXETINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate [IC50 31 uM]
moderate
moderate
moderate
yes (co-administration study)
Comment: addition of fluoxetine 20 mg/day to pre-existing risperidone therapy produced a mean 4- fold increase in plasma risperidone concentration, with some patients exhibiting an increase as large as 10-fold
no
strong [IC50 1.05 uM]
yes (co-administration study)
Comment: Coadministration of fluoxetine with other drugs that are metabolized by CYP2D6, including certain antidepressants (e.g., TCAs), antipsychotics (e.g., phenothiazines and most atypicals), and antiarrhythmics (e.g., propafenone, flecainide, and others) should be approached with caution
yes [IC50 14 uM]
yes [IC50 16 uM]
yes [IC50 3.32 uM]
yes [IC50 30 uM]
yes [IC50 5 uM]
yes [IC50 6.2 uM]
yes
yes
yes (co-administration study)
Comment: Fluoxetine dosing inhibited CYP2C19 activity in both age groups, increasing the (S)- to (R)-mephenytoin ratio 3- to 4-fold
Drug as victimTox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The potentiating effect of sertraline and fluoxetine on amphetamine-induced locomotor activity is not mediated by serotonin.
1999 Apr
Sildenafil in the treatment of female sexual dysfunction induced by selective serotonin reuptake inhibitors.
1999 Jun
Differential adaptation of brain 5-HT1A and 5-HT1B receptors and 5-HT transporter in rats treated chronically with fluoxetine.
2000
Antidepressant drugs appear to enhance cocaine-induced toxicity.
2000 Feb
Fluoxetine toxicity in a preterm infant.
2000 Oct-Nov
Evidence of early onset of antidepressant effect in randomized controlled trials.
2001
The effects of antidepressants on sexual functioning in depressed patients: a review.
2001
Incidence of sexual dysfunction associated with antidepressant agents: a prospective multicenter study of 1022 outpatients. Spanish Working Group for the Study of Psychotropic-Related Sexual Dysfunction.
2001
Effects of selective serotonin reuptake inhibitors on sexual function.
2001 Apr
Effect of chronic and acute administration of fluoxetine and its additive effect with morphine on the behavioural response in the formalin test in rats.
2001 Feb
Characterization of 5-HT receptors in the parasitic nematode, Ascaris suum.
2001 Feb
Influence of coadministration of fluoxetine on cisapride pharmacokinetics and QTc intervals in healthy volunteers.
2001 Feb
Evaluation of the potential pharmacokinetic interaction between almotriptan and fluoxetine in healthy volunteers.
2001 Feb
Psychopharmacologic treatment of adolescent depression.
2001 Feb
Citalopram-induced bruxism.
2001 Feb
Fluoxetine and side effects in the geriatric population.
2001 Feb 1
Treatment of bipolar depression with twice-weekly fluoxetine: management of antidepressant-induced mania.
2001 Jan
Augmented accumbal serotonin levels decrease the preference for a morphine associated environment during withdrawal.
2001 Jan
Regulation of GFRalpha-1 and GFRalpha-2 mRNAs in rat brain by electroconvulsive seizure.
2001 Jan
Effects of chronic antidepressant treatments on 5-HT and NA transporters in rat brain: an autoradiographic study.
2001 Jan
Brain function in a patient with torture related post-traumatic stress disorder before and after fluoxetine treatment: a positron emission tomography provocation study.
2001 Jan 12
Role of serotonin and noradrenaline in social dysfunction: a review of data on reboxetine and the Social Adaptation Self-evaluation Scale (SASS).
2001 Jan-Feb
Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants.
2001 Mar
Modafinil does not affect serotonin efflux from rat frontal cortex synaptosomes: comparison with known serotonergic drugs.
2001 Mar 16
Patents

Sample Use Guides

Usual Adult Dose for Bulimia Immediate-release oral formulations: Recommended dose: 60 mg orally once a day Usual Adult Dose for Depression Immediate-release oral formulations: Initial dose: 20 mg orally once a day, increased after several weeks if insufficient clinical improvement is observed Maintenance dose: 20 to 60 mg orally per day Maximum dose: 80 mg orally per day Delayed release oral capsules: Initial dose: 90 mg orally once a week, commenced 7 days after the last daily dose of immediate-release fluoxetine 20 mg formulations. Usual Adult Dose for Obsessive Compulsive Disorder Immediate-release oral formulations: Initial dose: 20 mg orally once a day, increased after several weeks if insufficient clinical improvement is observed. Maintenance dose: 20 to 60 mg orally per day Maximum dose: 80 mg orally per day Usual Adult Dose for Panic Disorder Immediate-release oral formulations: Initial dose: 10 mg orally once a day, increased after one week to 20 mg orally once a day Maintenance dose: 20 to 60 mg orally per day Maximum dose: 60 mg orally per day
Route of Administration: Oral
Caco-2 SERT was also shown to be a high affinity (Kt=0.216 uM) saturable, Na(+) -dependent transporter that was inhibited by fluoxetine (IC(50)=17.6 nM).
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:37 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:37 GMT 2025
Record UNII
I9W7N6B1KJ
Record Status Validated (UNII)
Record Version
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Name Type Language
SYMBYAX COMPONENT FLUOXETINE HYDROCHLORIDE
Preferred Name English
FLUOXETINE HYDROCHLORIDE
EP   GREEN BOOK   HSDB   JAN   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
LY-110140
Code English
FLUOXETINE HYDROCHLORIDE [JAN]
Common Name English
PROZAC
Brand Name English
FONTEX
Brand Name English
FLUNEURIN
Brand Name English
LY110140
Code English
FOXETIN
Brand Name English
FLUOX-PUREN
Brand Name English
Fluoxetine hydrochloride [WHO-DD]
Common Name English
FLUOXETINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
FLUOXETINE HYDROCHLORIDE [MI]
Common Name English
FLUOXETINE HYDROCHLORIDE [USAN]
Common Name English
FLUXET
Brand Name English
ADOFEN
Brand Name English
FLUOXETINE HYDROCHLORIDE [HSDB]
Common Name English
BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, HYDROCHLORIDE (1:1)
Systematic Name English
BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, HYDROCHLORIDE, (±)-
Systematic Name English
FLUOXETINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
RECONCILE
Brand Name English
FLUOXETINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
FLUOXETINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
SARAFEM
Brand Name English
FLUOXETINE HYDROCHLORIDE [USP-RS]
Common Name English
(±)-N-METHYL-3-PHENYL-3-((.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-P-TOLYL)OXY)PROPYLAMINE, HYDROCHLORIDE
Common Name English
FLUCTIN
Brand Name English
LOVAN
Brand Name English
FLUOXETINE (AS HYDROCHLORIDE)
Common Name English
FLUSOL
Brand Name English
FLUOXETINE HYDROCHLORIDE [VANDF]
Common Name English
FLUOXETINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
FLUOXEREN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
NCI_THESAURUS C265
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
Code System Code Type Description
DAILYMED
I9W7N6B1KJ
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
ECHA (EC/EINECS)
260-101-2
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
CHEBI
5118
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
RXCUI
227224
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY RxNorm
PUBCHEM
62857
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID7020635
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
HSDB
6633
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
RS_ITEM_NUM
1279804
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
CHEBI
5119
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
EVMPD
SUB02226MIG
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
USAN
AA-47
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
NCI_THESAURUS
C2829
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
SMS_ID
100000091555
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
DRUG BANK
DBSALT000087
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
FDA UNII
I9W7N6B1KJ
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
ChEMBL
CHEMBL41
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
MERCK INDEX
m5487
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY Merck Index
CAS
56296-78-7
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
PRIMARY
CAS
59333-67-4
Created by admin on Mon Mar 31 17:56:37 GMT 2025 , Edited by admin on Mon Mar 31 17:56:37 GMT 2025
SUPERSEDED
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
This impurity may not be present.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY