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Details

Stereochemistry RACEMIC
Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOXETINE

SMILES

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

InChI

InChIKey=RTHCYVBBDHJXIQ-UHFFFAOYSA-N
InChI=1S/C17H18F3NO/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

HIDE SMILES / InChI

Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Urinary retention with reboxetine-fluoxetine combination in a young man.
2000 Dec
Methadone, ciprofloxacin, and adverse drug reactions.
2000 Dec 16
Fluoxetine-induced sexual dysfunction reversed by trazodone.
2000 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
Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants.
2001
Fluoxetine: a review of its therapeutic potential in the treatment of depression associated with physical illness.
2001
Effects of selective serotonin reuptake inhibitors on sexual function.
2001 Apr
Anti-Inflammatory effects of antidepressants through suppression of the interferon-gamma/interleukin-10 production ratio.
2001 Apr
Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin.
2001 Apr
Fluoxetine pharmacokinetics and effect on CYP2C19 in young and elderly volunteers.
2001 Apr
Serotonergic manipulations both potentiate and reduce brain stimulation reward in rats: involvement of serotonin-1A receptors.
2001 Apr
Inhibition of phenytoin hydroxylation in human liver microsomes by several selective serotonin re-uptake inhibitors.
2001 Apr
Idazoxan and 8-OH-DPAT modify the behavioral effects induced by either NA, or 5-HT, or dual NA/5-HT reuptake inhibition in the rat forced swimming test.
2001 Apr
Social impulsivity inversely associated with CSF 5-HIAA and fluoxetine exposure in vervet monkeys.
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
Severe symptomatic hyponatremia during citalopram therapy.
2001 Feb
Evaluation of the potential pharmacokinetic interaction between almotriptan and fluoxetine in healthy volunteers.
2001 Feb
Long-term treatment of obsessive-compulsive disorder after an acute response: a comparison of fluoxetine versus placebo.
2001 Feb
Augmentation of fluoxetine's antidepressant action by pindolol: analysis of clinical, pharmacokinetic, and methodologic factors.
2001 Feb
The economic consequences of a drug-drug interaction.
2001 Feb
Dose-dependent seizure activity associated with fluoxetine therapy.
2001 Feb
Acute hypokalemic paralysis associated with long-term lithium therapy.
2001 Feb
Psychopharmacologic treatment of adolescent depression.
2001 Feb
Citalopram-induced bruxism.
2001 Feb
Female sexual dysfunction and antidepressant use.
2001 Feb
Fluoxetine and side effects in the geriatric population.
2001 Feb 1
A compulsive collecting behavior following an A-com aneurysmal rupture.
2001 Feb 13
Inhibition of shock-induced foot tapping behaviour in the gerbil by a tachykinin NK1 receptor antagonist.
2001 Feb 2
Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity.
2001 Feb 23
Benefits from mianserin augmentation of fluoxetine in patients with major depression non-responders to fluoxetine alone.
2001 Jan
Treatment of bipolar depression with twice-weekly fluoxetine: management of antidepressant-induced mania.
2001 Jan
Fluoxetine-induced Ca2+ signals in Madin-Darby canine kidney cells.
2001 Jan
Central 5-hydroxytryptamine-2A receptor expression in transgenic mice bearing a glucocorticoid receptor antisense.
2001 Jan
Effects of serotonin and fluoxetine on blood glucose regulation in two decapod species.
2001 Jan
Acute effect of different antidepressants on glycemia in diabetic and non-diabetic rats.
2001 Jan
Atrial arrhythmia in a woman treated with fluoxetine: is there a causal relationship?
2001 Jan
A novel augmentation strategy for treating resistant major depression.
2001 Jan
Depression among pregnant adolescents: an integrated treatment approach.
2001 Jan
In vitro study on fluoxetine adsorption onto charcoal using potentiometry.
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
No gender differences in placebo responses of patients with major depressive disorder.
2001 Jan 15
Fluoxetine (Sarafem) for premenstrual dysphoric disorder.
2001 Jan 22
Plasticity in serotonin uptake in primary neuronal cultures of serotonin transporter knockout mice.
2001 Jan 31
Antidepressants alter cell proliferation in the adult brain in vivo and in neural cultures in vitro.
2001 Jan 5
Regulation of the vesicular monoamine transporter-2: a novel mechanism for cocaine and other psychostimulants.
2001 Mar
Addition of a 5-HT receptor agonist to methylphenidate potentiates the reduction of [123I]FP-CIT binding to dopamine transporters in rat frontal cortex and hippocampus.
2001 Mar 1
Repeated electroconvulsive stimulation, but not antidepressant drugs, induces mossy fibre sprouting in the rat hippocampus.
2001 Mar 2
Adding group psychotherapy to medication treatment in dysthymia: a randomized prospective pilot study.
2001 Spring
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Tue Oct 22 00:22:45 UTC 2019
Edited
by admin
on Tue Oct 22 00:22:45 UTC 2019
Record UNII
01K63SUP8D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOXETINE
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
FLUOXETINE [INN]
Common Name English
(+/-)-N-METHYL-3-PHENYL-3-((.ALPHA.,ALPHA.,.ALPHA.-TRIFLUORO-P-TOLYL)OXY)PROPYLAMINE
Common Name English
FLUOXETIN RATIOPHARM
Common Name English
DL-N-METHYL-3-(P-TRIFLUOROMETHYLPHENOXY)-3-PHENYLPROPYLAMINE
Common Name English
FLUOXETINE [USAN]
Common Name English
NSC-283480
Code English
FLUOXETINE [EMA EPAR VETERINARY]
Common Name English
FLUOXETINE [WHO-DD]
Common Name English
FLUOXETINE [VANDF]
Common Name English
N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)BENZENEPROPANAMINE
Systematic Name English
FLUOXETINE [MI]
Common Name English
FLUVAL
Common Name English
BENZENEPROPANAMINE, N-METHYL-G-(4-(TRIFLUOROMETHYL)PHENOXY)-, (+/-)-
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 183504
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
NDF-RT N0000000109
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-ATC N06AB03
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
EMA VETERINARY ASSESSMENT REPORTS RECONCILE [AUTHORIZED]
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
FDA ORPHAN DRUG 123199
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
LIVERTOX 424
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-ATC N06CA03
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-VATC QN06AB03
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.2.1
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
NCI_THESAURUS C94725
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
CFR 21 CFR 520.980
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
NCI_THESAURUS C265
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
NDF-RT N0000175696
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
WHO-VATC QN06CA03
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
Code System Code Type Description
WIKIPEDIA
FLUOXETINE
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
MERCK INDEX
M5487
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY Merck Index
CAS
54910-89-3
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
ChEMBL
CHEMBL41
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
LactMed
54910-89-3
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
EVMPD
SUB07723MIG
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
RXCUI
4493
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C506
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
EPA CompTox
54910-89-3
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
IUPHAR
203
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
PUBCHEM
3386
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
INN
3883
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
DRUG BANK
DB00472
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
MESH
D005473
Created by admin on Tue Oct 22 00:22:45 UTC 2019 , Edited by admin on Tue Oct 22 00:22:45 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
POTENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
POTENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
CYP2D6 enzyme is involved in the metabolism of fluoxetine to norfluoxetine in patients under steady-state conditions
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
MAXIMUM TOLERATED DOSE TOXICITY RAPID METABOLIZERS OR THOSE WITH INADEQUATE RESPONSE AFTER 8 WEEKS

Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC NORFLUOXETINE
PHARMACOKINETIC
NORFLUOXETINE, LIVER CIRRHOSIS
PHARMACOKINETIC
LIVER CIRRHOSIS
PHARMACOKINETIC