{"ATC Code":["N06AB03","N06AB03","N - Nervous system","N06 - Psychoanaleptics","N06A - Antidepressants","N06AB - Selective serotonin reuptake inhibitors","N06AB03 - Fluoxetine","QN - Nervous system","QN06 - Psychoanaleptics","QN06A - Antidepressants","QN06AB - Selective serotonin reuptake inhibitors","QN06AB03 - Fluoxetine","N06AB03"],"Absorption, Distribution and Excretion":"The oral bioavailability of fluoxetine is \u003c90% as a result of hepatic first pass metabolism.  In a bioequivalence study, the Cmax of fluoxetine 20 mg for the established reference formulation was 11.754 ng/mL while the Cmax for the proposed generic formulation was 11.786 ng/ml.  Fluoxetine is very lipophilic and highly plasma protein bound, allowing the drug and it's active metabolite, norfluoxetine, to be distributed to the brain.","Adverse Effects":"The most common adverse effects reported by adults include insomnia, nausea, diarrhea, anorexia, dry mouth, headache, drowsiness, anxiety, nervousness, yawning, bruising, seizures, bleeding (rarely), hyperhidrosis, induction of mania, rare activation of suicidal ideation and behavior (especially in teenagers), weight gain/loss, decreased orgasm (anorgasmia and ejaculation latency), muscle weakness, tremors, and pharyngitis.","Aliases":["Fluoxetine","Fluoxetina","Animex-On","Fluval","Fluoxetinum","Fluoxetin","N-Methyl-γ-(4-(trifluoromethyl)phenoxy)benzenepropanamine","N-Methyl-3-phenyl-3-((α,α,α-trifluoro-p-tolyl)oxy)propylamine","Methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine","Dtxsid7023067","n-methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine","NSC-758685","CHEBI:5118","Dtxcid903067","Chebi:86990","Benzenepropanamine, N-methyl-γ-(4-(trifluoromethyl)phenoxy)-, (+-)-","N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine","methyl((3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl))amine","Lilly110140","N06AB03","N-methyl-γ-(4-(trifluoromethyl)-phenoxy)-benzenepropanamine","Pulvules","Portal","Eufor","N-Methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine","Fluoxetine-d5","CHEMBL41","3-(p-Trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine","Mfcd00072041","57226-07-0","NSC-283480","N-methyl-3-[4-(trifluoromethyl)phenoxy]-3-(3-tritiophenyl)propan-1-amine","HSDB 6633","Ncgc00015428-08","Methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine","methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amine hydrochloride","Cas-54910-89-3","fluoexetine","methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amine","Unii-01k63sup8d","Spectrum_001679","SpecPlus_000723","Prestwick0_000511","Prestwick1_000511","Prestwick2_000511","Prestwick3_000511","Spectrum2_001658","Spectrum3_001648","Spectrum4_000613","Spectrum5_001518","FluoxetineLY-110140","Benzenepropamine, N-methyl-γ-(4-(trifluoromethyl)phenoxy)-, (+-)-","Biomol-NT_000152","Epitope ID:224550","(+) or (-)-N-Methyl-γ-(4-(trifluoromethyl)phenoxy)benzenepropanamine","Schembl8353","LY-110140 free base","(+) or (-)-N-Methyl-3-phenyl-3-((α,α,α-trifluoro-p-tolyl)oxy)propylamine","Lopac0_000558","BSPBio_000461","BSPBio_003375","GTPL203","KBioGR_001166","KBioSS_002159","cid_62857","DivK1c_006819","SPBio_001815","SPBio_002382","BPBio1_000354","BPBio1_000509","orb1310603","orb3025526","BDBM30130","KBio1_001763","KBio2_002159","KBio2_004727","KBio2_007295","KBio3_002595","PS06 - Fluoxetine/Norfluoxetine","HMS2090H14","Albb-025606","HY-B0102","MSK10030","Tox21_110144","N-Methyl-3-p-(p-trifluoromethylphenoxy)-3-phenylpropylamine","N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine]","N-Methyl-γ-[4-(trifluoromethyl)phenoxy]benzenepropanamine","AB9783","BBL012251","EBC-00600","N-methyl-3-phenyl-3-{[4-(trifluoromethyl)phenyl]oxy}propan-1-amine","NS-140","NSC283480","SBB017267","STK734483","Akos003663021","Tox21_110144_1","AC-8478","CCG-204648","DB00472","NSC 283480","NSC 758685","Sdccgsbi-0050541.p004","N-Methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine","Ncgc00015428-06","Ncgc00015428-07","Ncgc00015428-10","Ncgc00015428-11","Ncgc00015428-12","Ncgc00015428-13","Ncgc00015428-15","Ncgc00015428-27","Ncgc00024879-03","Ncgc00024879-04","AS-44989","FF100299","ST076807","Sbi-0050541.p003","DB-015148","AB00053774","NS00000284","D00326","En300-199668","Ab00053774-13","Ab00053774-14","Ab00053774_15","Ab00053774_16","L000931","Brd-a31159102-001-01-9","Brd-a31159102-003-05-6","Brd-a31159102-003-16-3","Brd-a31159102-003-28-8","Brd-a31159102-003-29-6","Brd-a31159102-003-30-4","Sr-01000002988-18","N-methyl 3-(p-trifluoromethylphenoxy)-3-phenylpropylamine","N-Methyl-3-phenyl-3-(p-trifluoromethylphenoxy)propylamine","Benzenepropanamine, N-methyl-?-[4-(trifluoromethyl)phenoxy]-","benzenepropanamine, N-methyl-γ-[4-(trifluoromethyl)phenoxy]-","N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine #","Benzenepropanamine, N-methyl-γ-[4-(trifluoromethyl)phenoxy]-","N-methyl-γ-(4-(trifluoromethyl)phenoxy)benzenepropanamine","N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine","(.+/-.)-N-Methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine","(.+/-.)-N-Methyl-3-phenyl-3-[(α,la,α-trifluoro-p-tolyl)oxy]propylamine","Benzenepropanamine, N-methyl-γ-[4-(trifluoromethyl)phenoxy]-, (.+/-.)-","Benzenepropanamine, n-methyl-g-(4-(trifluoromethyl)phenoxy)-","N-methyl-3-phenyl-3-((α,α.,α-trifluoro-p-tolyl)oxy)propylamine"],"Biological Half-Life":"The half life of fluoxetine is significant with the elimination half-life of the parent drug averaging 1-3 days after acute administration, and 4-6 days after chronic administration. Further, the elimination half life of it's active metabolite, norfluoxetine, ranges from 4-16 days after both acute and chronic administration. The half-life of fluoxetine should be considered when switching patients from fluoxetine to another antidepressant since marked accumulation occurs after chronic use. Fluoxetine's long half-life may even be beneficial when discontinuing the drug since the risk of withdrawal is minimized.","Boiling Point":"395.1°C at 760 mmHg","CAS":"54910-89-3","Chemical Classes":"Pharmaceutical","ChemicalClasses":["phenylpropylamine"],"Chirality":"racemic","Classes":["Serotonin reuptake inhibitor"],"Drug Classes":["Breast Feeding","Lactation","Milk, Human","Antidepressive Agents","Serotonin Uptake Inhibitors"],"Drug Indication":"Fluoxetine is indicated for both acute and maintenance treatment of major depressive disorder, obsessive compulsive disorder, and bulimia nervosa; however, it is only indicated for acute treatment of panic disorder independent of whether agoraphobia is present. Fluoxetine may also be used in combination with olanzapine to treat depression related to Bipolar I Disorder, and treatment resistant depression. Fluoxetine is additionally indicated for the treatment of female patients with premenstrual dysphoric disorder (PMDD).","DurationOfAction":"","EliminationHalfLife":"1 – 3 days (acute)4 – 6 days (chronic)","Esters":[],"European Community (EC) Number":"611-209-7","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":29,"Value":{"StringWithMarkup":[{"String":"01K63SUP8D"}]}},{"Name":"Active Moiety","ReferenceNumber":29,"Value":{"StringWithMarkup":[{"String":"FLUOXETINE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":29,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Established Pharmacologic Class [EPC] - Serotonin Reuptake Inhibitor"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":29,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Mechanisms of Action [MoA] - Serotonin Uptake Inhibitors"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":29,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-3386","Length":10,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Fluoxetine"},{"Extra":"CID-5202","Length":9,"Start":16,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"},{"Extra":"CID-3386","Length":10,"Start":73,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/fluoxetine"},{"Extra":"CID-5202","Length":9,"Start":92,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Fluoxetine is a Serotonin Reuptake Inhibitor. The mechanism of action of fluoxetine is as a Serotonin Uptake Inhibitor."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":90,"Value":{"StringWithMarkup":[{"String":"FLUOXETINE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":90,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5202","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"},{"Extra":"CID-5202","Length":9,"Start":35,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Serotonin"}],"String":"Serotonin Uptake Inhibitors [MoA]; Serotonin Reuptake Inhibitor [EPC]"}]}}],"Formating":[],"HMDB ID":"HMDB0014615","Health Effects":"Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.  Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur.  Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.","HeavyAtomCount":22,"Human Drugs":"Antidepressants -\u003e Selective serotonin reuptake inhibitors (SSRI)","IUPACName":"N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine","InChI":"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","InChIKey":"RTHCYVBBDHJXIQ-UHFFFAOYSA-N","KEGG Entries":[{"Id":"D00326","Interactions":[{"Action":"inhibition","Target":"CYP2D6"},{"Action":"inhibition","Target":"CYP2C9"},{"Action":"inhibition","Target":"CYP2C19"},{"Action":"inhibition","Target":"CYP3A"},{"Action":"induction","Target":"CYP2C9"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Fluoxetine","Fluoxetine"]},{"Id":"D00823","Interactions":[{"Action":"inhibition","Target":"CYP2D6"},{"Action":"inhibition","Target":"CYP2C9"},{"Action":"inhibition","Target":"CYP2C19"},{"Action":"inhibition","Target":"CYP3A"},{"Action":"induction","Target":"CYP2C9"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Fluoxetine hydrochloride","Prozac","Sarafem"]},{"Id":"D00326","Interactions":[{"Action":"inhibition","Target":"CYP2D6"},{"Action":"inhibition","Target":"CYP2C9"},{"Action":"inhibition","Target":"CYP2C19"},{"Action":"inhibition","Target":"CYP3A"},{"Action":"induction","Target":"CYP2C9"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Fluoxetine","Fluoxetine"]},{"Id":"D00823","Interactions":[{"Action":"inhibition","Target":"CYP2D6"},{"Action":"inhibition","Target":"CYP2C9"},{"Action":"inhibition","Target":"CYP2C19"},{"Action":"inhibition","Target":"CYP3A"},{"Action":"induction","Target":"CYP2C9"},{"Action":"induction","Target":"CYP2D6"}],"Synonyms":["Fluoxetine hydrochloride","Prozac","Sarafem"]}],"MeSH Headers":[{"Id":"M0008635","Link":"https://id.nlm.nih.gov/mesh/M0008635.html","Name":"Fluoxetine","Ref":131},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":133},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":163},{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":164},{"Id":"M0556972","Link":"https://id.nlm.nih.gov/mesh/M0556972.html","Name":"Selective Serotonin Reuptake Inhibitors","Ref":165},{"Id":"M0590381","Link":"https://id.nlm.nih.gov/mesh/M0590381.html","Name":"Cytochrome P-450 CYP2D6 Inhibitors","Ref":166}],"MeSH Pharmacological Classification":[{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":164},{"Id":"M0556972","Link":"https://id.nlm.nih.gov/mesh/M0556972.html","Name":"Selective Serotonin Reuptake Inhibitor","Ref":165},{"Id":"M0590381","Link":"https://id.nlm.nih.gov/mesh/M0590381.html","Name":"Cytochrome P-450 CYP2D6 Inhibitor","Ref":166}],"Mechanism of Action":"The monoaminergic hypothesis of depression emerged in 1965 and linked depression with dysfunction of neurotransmitters such as noradrenaline and serotonin. Indeed, low levels of serotonin have been observed in the cerebrospinal fluid of patients diagnosed with depression. As a result of this hypothesis, drugs that modulate levels of serotonin such as fluoxetine were developed.  Fluoxetine is a selective serotonin reuptake inhibitor (SSRI) and as the name suggests, it exerts it's therapeutic effect by inhibiting the presynaptic reuptake of the neurotransmitter serotonin. As a result, levels of 5-hydroxytryptamine (5-HT) are increased in various parts of the brain. Further, fluoxetine has high affinity for 5-HT transporters, weak affinity for noradrenaline transporters and no affinity for dopamine transporters indicating that it is 5-HT selective.  Fluoxetine interacts to a degree with the 5-HT\u003csub\u003e2C\u003c/sub\u003e receptor and it has been suggested that through this mechanism, it is able to increase noradrenaline and dopamine levels in the prefrontal cortex.","Melting Point":"179 - 182 °C","Metabolism/Metabolites":"Fluoxetine is metabolized to norfluoxetine by CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP3A4, and CYP3A5 upon ingestion. Although all of the mentioned enzymes contribute to N-demethylation of fluoxetine, CYP2D6, CYP2C9 and CYP3A4 appear to be the major contributing enzymes for phase I metabolism. In addition, there is evidence to suggest that CYP2C19 and CYP3A4 mediate O-dealkylation of fluoxetine and norfluoxetine to produce para-trifluoromethylphenol which is subsequently metabolized to hippuric acid. Both fluoxetine and norfluoxetine undergo glucuronidation to facilitate excretion.   Notably, both the parent drug and active metabolite inhibit CYP2D6 isozymes, and as a result patients who are being treated with fluoxetine are susceptible to drug interactions.","MolecularFormula":"C\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eF\u003csub\u003e3\u003c/sub\u003eNO","MolecularWeight":"309.33 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"Fluoxetine blocks the serotonin reuptake transporter in the presynaptic terminal, which ultimately results in sustained levels of 5-hydroxytryptamine (5-HT) in certain brain areas. However, fluoxetine binds with relatively poor affinity to 5-HT, dopaminergic, adrenergic, cholinergic, muscarinic, and histamine receptors which explains why it has a far more desirable adverse effect profile compared to earlier developed classes of antidepressants such as tricyclic antidepressants.","Physical Description":"Solid","PubChemId":3386,"Record Description":["LiverTox|CNS|Antidepressant|SSRI"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"5838","RefCount":4,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Fluoxetine","Name":"Fluoxetine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q422244","Name":"Fluoxetine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00472","Name":"Fluoxetine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/3386","Name":"Fluoxetine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=54910-89-3","Name":"Fluoxetine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014615","Name":"Fluoxetine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D00326","Name":"Fluoxetine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/01K63SUP8D","Name":"Fluoxetine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID7023067","Name":"Fluoxetine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 3386, Fluoxetine. Accessed April 15, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/3386\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/3386\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Fluoxetine. UNII: 01K63SUP8D. Global Substance Registration System. Accessed April 15, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/01K63SUP8D\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/01K63SUP8D\u003c/a\u003e","Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017. June 21, 2022. 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d=\"M40.638 51.092v5.66M43.916 45.278l4.96-2.863\" class=\"hi\"/\u003e\u003cpath stroke=\"#90e050\" d=\"m86.847 5.241 3.232 5.433M103.839 9.842l-5.263 3.132M99.023 25.704l-2.856-4.799\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Title":"Fluoxetine","Toxicity Data":" LD\u003csub\u003e50\u003c/sub\u003e=284mg/kg (orally in mice). ","Treatment":"If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.","UNII":"01K63SUP8D","Wikidata":"Q422244","Wikipedia":"Fluoxetine","XLogP":4}