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
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
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
Sources: http://adisinsight.springer.com/drugs/800013380
Curator's Comment: # Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
10.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PROZAC Approved UseFluoxetine 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 Date1987 |
|||
Primary | PROZAC Approved UseFluoxetine 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 Date1987 |
|||
Primary | PROZAC Approved UseFluoxetine 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 Date1987 |
|||
Primary | PROZAC Approved UseFluoxetine 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 Date1987 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.56 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15968712 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16229112 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1101.46 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15968712 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16229112 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
46.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15968712 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16229112 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.5% |
FLUOXETINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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 Sources: https://pubmed.ncbi.nlm.nih.gov/12172343/ |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/31037729/ |
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 Sources: https://pubmed.ncbi.nlm.nih.gov/11270912/ |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
yes [Ki 19 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/fluoxetine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601320
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
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admin
on
Edited
Mon Mar 31 17:56:37 GMT 2025
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Record UNII |
I9W7N6B1KJ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C94725
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NCI_THESAURUS |
C265
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260-101-2
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DTXSID7020635
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AA-47
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C2829
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100000091555
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m5487
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56296-78-7
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59333-67-4
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SUPERSEDED |
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
This impurity may not be present.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |