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Drug

D0060 | Fluoxetine

Molecular Formula C17H18F3NO
Molecular Weight 309.33
Structure
State solid
Volume of distribution * 20-45 L/kg
Route of elimination The primary route of elimination appears to be hepatic metabolism to inactive metabolites excreted by the kidney. The S-enantiomer is eliminated more slowly and is the predominant enantiomer present at steady state.
Protein binding 94.5% bound to human serum proteins, including albumin and alpha-1-glycoprotein.
Half life 1-3 days [acute administration]; 4-6 days [chronic administration]; 4-16 days [norfluoxetine, acute and chronic administration].
Absorption Well absorbed from the GI tract following oral administration. Oral bioavailability is estimated to be at least 60-80%. Peak plasma concentrations occur within 6-8 hours following a single oral administration of a 40 mg dose. The oral solution and delayed-release capsule are bioequivalent. Food does not affect the systemic bioavailability of fluoxetine but it delays the absorption by 1-2 hours (not clinically significant). Prozac Weekly capsules, a delayed–release formulation, contain enteric–coated pellets that resist dissolution until reaching a segment of the gastrointestinal tract where the pH exceeds 5.5. The enteric coating delays the onset of absorption of fluoxetine 1 to 2 hours relative to the immediate–release formulations.
Trade names Prozacm, Sarafem, Adofen
Description selective serotonin reuptake inhibitor (SSRI); 2nd generation antidepressant;

N

N06CA03 Fluoxetine and psycholeptics


[N06CA] Antidepressants in combination with psycholeptics


[N06C] PSYCHOLEPTICS AND PSYCHOANALEPTICS IN COMBINATION


[N06] PSYCHOANALEPTICS


[N] Nervous system

N06AB03 Fluoxetine


[N06AB] Selective serotonin reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELECTROPHORETIC UNCOUPLING 278
RESPIRATION decrease 307
ELECTRON TRANSPORT CHAIN rat brain mitochondria decrease 307
ELECTRON TRANSPORT CHAIN rat liver mitochondria decrease 307
GLUCOSE GALACTOSE IC50 RATIO 63.4 ± 8.1, 43.1 ± 9.6 ,1.5, 58.0 ± 15.1, 63.3 ± 26.2, 0.9 4hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50
SHAPE Change 307
BIOGENESIS decrease 307
MITOCHONDRIA TRANSPORT 3 μM rat Hippocampal Neurons time-lapse imaging experiments increase 215

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase Inhibition 307
Quinol--cytochrome-c reductase Inhibition 307
Cytochrome c oxidase Inhibition 307
Caspase-3 increase 307

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 4 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]


H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]


H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]


H336 (100%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure


Narcotic effects]


H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P260, P261, P264, P270, P271, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P330, P332+P313, P362, P391, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 oral 248mg/kg (248mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
child TDLo oral 26mg/kg (26mg/kg) Journal of the American Academy of Child and Adolescent Psychiatry. Vol. 28, Pg. 587, 1989.
women TDLo oral 17mg/kg/2W-I (17mg/kg) behavioral: anorexia (human Journal of Clinical Psychiatry. Vol. 55, Pg. 118, 1994.
women TDLo oral 28mg/kg/7W-I (28mg/kg) lungs, thorax, or respiration: dyspnea Medical Journal of Australia. Vol. 156, Pg. 364, 1992.
women TDLo oral 5600ug/kg/2W- (5.6mg/kg) skin and appendages (skin): hair: other British Journal of Psychiatry. Vol. 159, Pg. 737, 1991.
dog LD oral > 100mg/kg (100mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
women TDLo oral 2800ug/kg/1W- (2.8mg/kg) behavioral: somnolence (general depressed activity) Journal of Clinical Psychiatry. Vol. 55, Pg. 118, 1994.
women TDLo oral 8mg/kg/4W-I (8mg/kg) Journal of Clinical Psychiatry. Vol. 54, Pg. 235, 1993.
cat LD oral > 50mg/kg (50mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
man TDLo oral 208mg/kg/2Y-I (208mg/kg) Mayo Clinic Proceedings. Vol. 74, Pg. 692, 1999.
rat LD50 oral 452mg/kg (452mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
man TDLo oral 12mg/kg/8W-I (12mg/kg) behavioral: "hallucinations, distorted perceptions" American Journal of Psychiatry. Vol. 150, Pg. 1750, 1993.
man TDLo oral 3733ug/kg/24H (3.733mg/kg) American Journal of Psychiatry. Vol. 143, Pg. 686, 1985.
women TDLo oral 800ug/kg/2D-I (0.8mg/kg) Journal of Clinical Psychiatry. Vol. 52, Pg. 174, 1991.
women TDLo oral 5600ug/kg/2W- (5.6mg/kg) Journal of Clinical Psychiatry. Vol. 54, Pg. 432, 1993.
women TDLo oral 400ug/kg (0.4mg/kg) behavioral: excitement Journal of Clinical Psychiatry. Vol. 50, Pg. 339, 1989.
guinea pig LD oral > 250mg/kg (250mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
monkey LD oral > 50mg/kg (50mg/kg) Journal of Clinical Psychiatry. Vol. 46(3, Pg. Sec,
mouse LD50 intraperitoneal 100mg/kg (100mg/kg) Toxicology and Applied Pharmacology. Vol. 32, Pg. 129, 1975.
women TDLo oral 8400ug/kg/3W- (8.4mg/kg) Annals of Emergency Medicine. Vol. 20, Pg. 194, 1991.
human TDLo oral 7770ug/kg (7.77mg/kg) American Journal of Emergency Medicine. Vol. 10, Pg. 115, 1992.
women TDLo oral 13600ug/kg (13.6mg/kg) Journal of Toxicology, Clinical Toxicology. Vol. 27, Pg. 389, 1989.

  • Abdominal discomfort

  • Abdominal distension

  • Affect lability

  • Affective disorder

  • Agitation

  • Agoraphobia

  • Anger

  • Anxiety

  • Asthenia

  • Binge eating

  • Bipolar I disorder

  • Bradyphrenia

  • Breast tenderness

  • Chest pain

  • Chills

  • Choking sensation

  • Compulsions

  • Depressed mood

  • Discomfort

  • Disturbance in attention

  • Drug abuse

  • Drug interaction

  • Dysphoria

  • Dyspnoea

  • Dysthymic disorder

  • Emotional distress

  • Fatigue

  • Fear of death

  • Feeling guilty

  • Flatulence

  • Foetor hepaticus

  • Headache

  • Hepatocellular injury

  • Hot flush

  • Hyperhidrosis

  • Hypersomnia

  • Hypoaesthesia

  • Insomnia

  • Irritability

  • Malaise

  • Menopausal symptoms

  • Mental disability

  • Mood swings

  • Musculoskeletal discomfort

  • Myalgia

  • Nausea

  • Nephropathy

  • Obsessive-compulsive disorder

  • Obsessive rumination

  • Obsessive thoughts

  • Panic attack

  • Panic disorder

  • Panic reaction

  • Premenstrual dysphoric disorder

  • Premenstrual syndrome

  • Purging

  • Renal failure

  • Renal impairment

  • Sensory loss

  • Suicidal ideation

  • Suicide attempt

  • Swelling

  • Tension

  • Tourette's disorder

  • Tremor

  • Vomiting

  • Weight increased

  • Abdominal pain

  • Abnormal dreams

  • Affect lability

  • Anxiety

  • Asthenia

  • Back pain

  • Body temperature increased

  • Constipation

  • Decreased appetite

  • Depression

  • Dermatitis

  • Diarrhoea

  • Disturbance in sexual arousal

  • Dizziness

  • Dry mouth

  • Dysmenorrhoea

  • Dyspepsia

  • Ejaculation disorder

  • Erectile dysfunction

  • Flatulence

  • Gastrointestinal disorder

  • Gastrointestinal pain

  • Headache

  • Hyperhidrosis

  • Infection

  • Influenza

  • Injury

  • Insomnia

  • Libido decreased

  • Menstrual disorder

  • Mental disability

  • Mood swings

  • Musculoskeletal discomfort

  • Myalgia

  • Nausea

  • Nervousness

  • Pain

  • Palpitations

  • Pharyngitis

  • Pollakiuria

  • Pruritus

  • Rash

  • Rhinitis

  • Sinusitis

  • Somnolence

  • Tension

  • Thinking abnormal

  • Tremor

  • Upper respiratory tract infection

  • Urinary tract infection

  • Visual impairment

  • Vomiting

  • Weight decreased

  • Yawning

    • (+) or (-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-p-tolyl)oxy)propylamine (+) or (-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine (+-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-p-tolyl)oxy)propylamine
    (+-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine (+/-) -Fluoxetine (+/-)-Fluoxetine
    (+/-)-N-Methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine (+/-)-N-Methyl-3-p-(p-trifluoromethylphenoxy)-3-phenylpropylamine (+/-)-N-Methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
    (+/-)-N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine] (+/-)-N-Methyl-gamma-[4-(trifluoromethyl)phenoxy]benzenepropanamine (.+/-.)-N-Methyl-3-phenyl-3-[(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)oxy]propylamine
    (.+/-.)-N-Methyl-3-phenyl-3-[(.alpha.,la,.alpha.-trifluoro-p-tolyl)oxy]propylamine 3-(p-Trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine 54910-89-3
    57226-07-0 AB00053774 AB00053774-13
    AB00053774-14 AB00053774_15 AB00053774_16
    AB0107059 AC-8478 AKOS003663021
    ALBB-025606 API0002736 AS-44989
    Animex-On BBL012251 BCP28440
    BDBM30130 BEN445 BPBio1_000354
    BPBio1_000509 BRD-A31159102-001-01-9 BRD-A31159102-003-05-6
    BRD-A31159102-003-16-3 BSPBio_000461 BSPBio_003375
    Benzenepropamine, N-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (+-)- Benzenepropanamine, N-methyl-.gamma.-[4-(trifluoromethyl)phenoxy]-, (.+/-.)- Benzenepropanamine, N-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (+-)-
    Benzenepropanamine, N-methyl-gamma-[4-(trifluoromethyl)phenoxy]-, (+/-)- Benzenepropanamine, N-methyl-|A-[4-(trifluoromethyl)phenoxy]- Biomol-NT_000152
    C-34924 CAS-54910-89-3 CC-28508
    CCG-204648 CHEBI:5118 CHEBI:86990
    CHEMBL41 CS-2861 CTK8D4092
    D00326 DB-015148 DB00472
    DSSTox_CID_3067 DSSTox_GSID_23067 DSSTox_RID_76861
    DTXSID7023067 DivK1c_006819 EN300-199668
    Epitope ID:224550 Eufor FT-0626489
    Fluoxetin Fluoxetina Fluoxetina [INN-Spanish]
    Fluoxetina [Spanish] Fluoxetine (TN) Fluoxetine (USAN/INN)
    Fluoxetine [USAN:INN:BAN] Fluoxetinum Fluoxetinum [INN-Latin]
    Fluval GTPL203 HMS2090H14
    HY-B0102 KBio1_001763 KBio2_002159
    KBio2_004727 KBio2_007295 KBio3_002595
    KBioGR_001166 KBioSS_002159 L000931
    LS-31040 LY-110140;LY 110140;LY110140 Lilly-110140
    Lopac0_000558 Methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine Methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
    N-Methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine N-Methyl-3-phenyl-3-(p-trifluoromethylphenoxy)propylamine N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine
    N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine # N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine N-methyl 3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
    N-methyl-3-[4-(trifluoromethyl)phenoxy]-3-(3-tritiophenyl)propan-1-amine N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
    N-methyl-3-phenyl-3-{[4-(trifluoromethyl)phenyl]oxy}propan-1-amine NCGC00015428-06 NCGC00015428-07
    NCGC00015428-08 NCGC00015428-10 NCGC00015428-11
    NCGC00015428-12 NCGC00015428-13 NCGC00015428-15
    NCGC00024879-03 NCGC00024879-04 NS-140
    NSC-283480 NSC283480 Portal
    Prestwick0_000511 Prestwick1_000511 Prestwick2_000511
    Prestwick3_000511 Pulvules Q422244
    RTHCYVBBDHJXIQ-UHFFFAOYSA-N Reconcile SBB017267
    SBI-0050541.P003 SC-46324 SCHEMBL8353
    SPBio_001815 SPBio_002382 ST076807
    STK734483 Selfemra SpecPlus_000723
    Spectrum2_001658 Spectrum3_001648 Spectrum4_000613
    Spectrum5_001518 Spectrum_001679 Symbyax
    TC-070879 Tox21_110144 Tox21_110144_1
    ZX-AN024120 benzenepropanamine, N-methyl-gamma-[4-(trifluoromethyl)phenoxy]- cid_62857
    dl-3-(p-Trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine fluoxetine fluoxetine (Prozac)
    methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amine methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amine hydrochloride n-methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine

    DrugBank Name Fluoxetine
    DrugBank DB00472
    CAS Number 100568-02-3, 114247-06-2, 154039-60-8, 54910-89-3, 56296-78-7, 57226-07-0, 59333-67-4
    PubChem Compound 3386
    KEGG Drug D00823
    PubChem.Substance 46507902
    ChEBI 86990
    PharmGKB PA449673
    ChemSpider 3269
    BindingDB 30130.0
    TTD DAP000186
    Wikipedia Fluoxetine
    DPD 11130

    1. Chan et al. (2005)