1.02009-07-21 20:26:59 UTC2026-05-14 16:39:50 UTCT3D2802FluoxetineSmallMoleculeFluoxetine belongs to the trifluoromethylbenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous compound has the formula C17H18F3NO and an average molecular weight of 309.33 g/mol. At room temperature, it exists as a solid.
Fluoxetine functions as a serotonin uptake inhibitor and an antidepressant (PMC8933701). It is a selective serotonin-reuptake inhibitor (SSRI) that blocks the reuptake of serotonin at the neuronal membrane's serotonin reuptake pump, which enhances the actions of serotonin on 5HT1A autoreceptors. It binds to histamine, acetylcholine, and norepinephrine receptors with significantly less affinity than tricyclic antidepressant drugs. Its protein targets include the sodium-dependent serotonin transporter (SLC6A4), and it acts as an antagonist of the sodium-dependent noradrenaline transporter (SLC6A2), sodium-dependent dopamine transporter (SLC6A3), acetylcholinesterase (ACHE), and voltage-gated inwardly rectifying potassium channel KCNH2, among 16 other proteins.
Therapeutically, fluoxetine is used for the treatment of depression (PMC11308527, PMC12800756), major depressive disorder (PMC7603145), and tuberculosis (PMC10979413), and it has a therapeutic effect on depression (PMC11563972). The recorded exposure route is oral. Fluoxetine has been found in 21 recorded sources, including drinking water and water supply; healthcare, pharmaceuticals, and veterinary products such as psycholeptics and psychoanaleptics in combination and antidepressants; household cleaning and consumer products including tobacco smoke filters and simulated smoking devices; food, food processing, and cookware; and electrical and electronic equipment.DrugSynthetic ToxinOrganic CompoundAmineOrganofluorideEtherDrugSelective Serotonin Reuptake InhibitorSerotonin Uptake InhibitorAntidepressant, Second-GenerationMetaboliteSerotonin AgentSynthetic CompoundAntidepressive Agent, Second-Generation(+-)-N-Methyl-3-phenyl-3-((alpha,alpha,alpha-trifluoro-P-tolyl)oxy)propylamine(+-)-N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine(+/-) -FluoxetineAdofenAnimex-OnFluoxerenFluoxetinfluoxetinFluoxetinaFluoxétineFluoxetinumFontexLadoseProzacSarafemC17H18F3NO309.3261309.134048818methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})aminefluoxetine54910-89-3CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1InChI=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,11-12H2,1H3RTHCYVBBDHJXIQ-UHFFFAOYSA-NOrganic compoundsBenzenoidsBenzene and substituted derivativesTrifluoromethylbenzenesTrifluoromethylbenzenesAlkyl aryl ethersAlkyl fluoridesAralkylaminesDialkylaminesHydrocarbon derivativesOrganofluoridesOrganopnictogen compoundsPhenol ethersPhenoxy compoundsAlkyl aryl etherAlkyl fluorideAlkyl halideAmineAralkylamineAromatic homomonocyclic compoundEtherHydrocarbon derivativeOrganic nitrogen compoundOrganic oxygen compoundOrganofluorideOrganohalogen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenol etherPhenoxy compoundSecondary aliphatic amineSecondary amineTrifluoromethylbenzeneAromatic homomonocyclic compounds(trifluoromethyl)benzenesaromatic ethersecondary amino compoundDetected and Not QuantifiedExogenousMembraneFluoxetine Action PathwaySMP0000426Fluoxetine Metabolism PathwaySMP0000646Tramadol Metabolism Pathway (New)SMP0125354Fluoxetine - Serotonin reuptake Inhibition Action PathwaySMP0126435Fluoxetine Drug Metabolism Action PathwaySMP0142926SolidWhite powder.melting_point179-182°Csolubility50 mg/mL at 25°Clogp4.05logp4.09ALOGPSlogs-5.26ALOGPSsolubility1.70e-03 g/lALOGPSlogp4.17ChemAxonpka_strongest_basic9.8ChemAxoniupacmethyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amineChemAxonaverage_mass309.3261ChemAxonmono_mass309.134048818ChemAxonsmilesCNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1ChemAxonformulaC17H18F3NOChemAxoninchiInChI=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,11-12H2,1H3ChemAxoninchikeyRTHCYVBBDHJXIQ-UHFFFAOYSA-NChemAxonpolar_surface_area21.26ChemAxonrefractivity80.37ChemAxonpolarizability30.33ChemAxonrotatable_bond_count7ChemAxonacceptor_count2ChemAxondonor_count1ChemAxonphysiological_charge1ChemAxonformal_charge0ChemAxonWell 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.Fluoxetine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
LD<sub>50</sub>=284mg/kg (orally in mice).Limited data from animal studies suggest that fluoxetine may undergo first-pass metabolism may occur via the liver and/or lungs. Fluoxetine appears to be extensively metabolized, likely in the liver, to norfluoxetine and other metabolites. Norfluoxetine, the principal active metabolite, is formed via <i>N</i>-demethylation of fluoxetine. Norfluoxetine appears to be comparable pharmacologic potency as fluoxetine. Fluoxetine and norfluoxetine both undergo phase II glucuronidation reactions in the liver. It is also thought that fluoxetine and norfluoxetine undergo <i>O</i>-dealkylation to form <i>p</i>-trifluoromethylphenol, which is then subsequently metabolized to hippuric acid.
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.
Half Life: 1-3 days [acute administration];
4-6 days [chronic administration];
4-16 days [norfluoxetine, acute and chronic administration]. LD<sub>50</sub>=284mg/kg (orally in mice). No indication of carcinogenicity to humans (not listed by IARC).Labeled indication include: major depressive disorder (MDD), moderate to severe bulimia nervosa, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), panic disorder with or without agoraphobia, and combination treatment with olanzapine for treatment-resistant or bipolar I depression. Unlabeled indications include: selective mutism, mild dementia-associated agitation in nonpsychotic patients, post-traumatic stress disorder (PTSD), social anxiety disorder, chronic neuropathic pain, fibromyalgia, and Raynaud's phenomenon. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7225dd55b0>Symptoms of overdose include agitation, restlessness, hypomania, and other signs of CNS excitation. The most frequent side effects include: nervous system effects such as anxiety, nervousness, insomnia, drowsiness, fatigue or asthenia, tremor, and dizziness or lightheadedness; GI effects such as anorexia, nausea, and diarrhea; vasodilation; dry mouth; abnormal vision; decreased libido; abnormal ejaculation; rash; and sweating. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity. 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.DB00472HMDB146153386CHEMBL4132695118FluoxetineFluoxetine76236094549929931551196404899416386Drugs.com: http://www.drugs.com/cons/Fluoxetine.htmlRxList: The Internet Drug Index (2009).: http://www.rxlist.com/BE0000749Metabolized to norfluoxetine, fluoxetine is a selective serotonin-reuptake inhibitor (SSRI), it blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT<sub>1A</sub> autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.Inhibitory0.00072uMBindingDB 30130Inhibitory0.00081uMBindingDB 30130Inhibitory0.0009uMBindingDB 30130Inhibitory0.0011uMBindingDB 30130Inhibitory0.0014uMBindingDB 81875Inhibitory0.002uMBindingDB 30130Inhibitory0.0022uMBindingDB 30130Inhibitory0.0035uMBindingDB 30130Inhibitory0.0057uMBindingDB 30130Inhibitory0.007uMBindingDB 30130Inhibitory0.0103uMBindingDB 30130Inhibitory0.013uMBindingDB 81875Inhibitory0.02uMBindingDB 30130Inhibitory0.048uMBindingDB 30130IC500.0025uMBindingDB 30130IC500.0031uMBindingDB 30130IC500.0052uMBindingDB 30130IC500.0073uMBindingDB 30130IC500.0094uMBindingDB 30130IC500.01uMBindingDB 30130IC500.016uMBindingDB 30130IC500.0324uMBindingDB 30130IC500.0394uMBindingDB 30130IC500.047uMBindingDB 30130IC500.18uMBindingDB 30130Dissociation0.00081uMBindingDB 30130BE0000486Inhibitory0.686uMBindingDB 81875Inhibitory0.777uMBindingDB 30130Inhibitory1.022uMBindingDB 30130Inhibitory1.56uMBindingDB 30130Inhibitory2uMBindingDB 30130Inhibitory2.186uMBindingDB 30130Inhibitory0.24uMBindingDB 30130Inhibitory0.41uMBindingDB 81875Inhibitory0.44uMBindingDB 30130Inhibitory0.574uMBindingDB 30130Inhibitory0.599uMBindingDB 30130IC500.563uMBindingDB 30130IC501.02uMBindingDB 30130IC502uMBindingDB 30130IC505.2uMBindingDB 30130Dissociation0.24uMBindingDB 30130BE0000647Inhibitory1.9uMBindingDB 30130Inhibitory3.097uMBindingDB 81875Inhibitory3.6uMBindingDB 30130Inhibitory3.764uMBindingDB 30130Inhibitory4.752uMBindingDB 30130Inhibitory4.974uMBindingDB 81875Inhibitory5.96uMBindingDB 30130Inhibitory6uMBindingDB 30130Inhibitory6.67uMBindingDB 30130IC504.4uMBindingDB 30130IC506uMBindingDB 30130IC5019.5uMBindingDB 30130Dissociation3.6uMBindingDB 30130BE0000090IC501.51356uMBindingDB 30130IC501.514uMBindingDB 30130IC503.1uMBindingDB 30130BE0000533Inhibitory0.1122uMBindingDB 30130Inhibitory0.28uMBindingDB 30130Inhibitory0.39811uMBindingDB 30130BE0000968Inhibitory7.3uMBindingDB 30130BE0000393Inhibitory5.03uMBindingDB 30130Inhibitory>10uMBindingDB 30130BE0000451Inhibitory0.14791uMBindingDB 30130Inhibitory0.24547uMBindingDB 30130BE0000289Inhibitory3.09uMBindingDB 30130Inhibitory>10uMBindingDB 30130BE0000442Inhibitory1.1uMBindingDB 30130Inhibitory5.4uMBindingDB 30130BE0000092Inhibitory0.702uMBindingDB 30130Inhibitory0.998uMBindingDB 81875Inhibitory1.03uMBindingDB 30130BE0000560Inhibitory0.59uMBindingDB 30130Inhibitory2.7uMBindingDB 30130BE0000291Inhibitory>10uMBindingDB 30130BE0000426IC50>10uMBindingDB 30130BE0004552BE0000045Inhibitory1uMBindingDB 30130BE0000405Inhibitory2.9uMBindingDB 30130BE0000156IC500.851uMBindingDB 30130BE0000738BE0003585BE0003584