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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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency
10.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROZAC
Primary
PROZAC
Primary
PROZAC
Primary
PROZAC

Cmax

ValueDoseCo-administeredAnalytePopulation
22.56 ng/mL
20 mg single, oral
FLUOXETINE plasma
Homo sapiens
13576.38 pg/mL
20 mg single, oral
FLUOXETINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1101.46 ng × h/mL
20 mg single, oral
FLUOXETINE plasma
Homo sapiens
788626.72 pg × h/mL
20 mg single, oral
FLUOXETINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
46.39 h
20 mg single, oral
FLUOXETINE plasma
Homo sapiens
49.7 h
20 mg single, oral
FLUOXETINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5.5%
FLUOXETINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Record UNII
I9W7N6B1KJ
Record Status Validated (UNII)
Record Version