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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-22 02:16:52 UTC
HMDB IDHMDB0014615
Secondary Accession Numbers
  • HMDB14615
StatusExpected but not Quantified
Metabolite Identification
Common NameFluoxetine
DescriptionFluoxetine hydrochloride is the first agent of the class of antidepressants known as selective serotonin-reuptake inhibitors (SSRIs). 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. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Flouxetine may be used to treat major depressive disorder (MDD), moderate to severe bulimia nervosa, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), panic disorder with or without agoraphobia, and in combination with olanzapine for treatment-resistant or bipolar I depression. Fluoxetine is the most anorexic and stimulating SSRI.
Structure
Thumb
Synonyms
ValueSource
SarafemChEMBL
SymbyaxChEMBL
ProzacChEMBL
Fluoxetine hydrochlorideMeSH
N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamineMeSH
FluoxetinMeSH
Chemical FormulaC17H18F3NO
Average Molecular Weight309.3261
Monoisotopic Molecular Weight309.134048818
IUPAC Namemethyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine
Traditional Namefluoxetine
CAS Registry Number54910-89-3
SMILES
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
InChI Identifier
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
InChI KeyRTHCYVBBDHJXIQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Subcellular:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point179 - 182 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.70e-03 g/LNot Available
LogP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 mg/mLALOGPS
logP4.09ALOGPS
logP4.17ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.37 m3·mol-1ChemAxon
Polarizability30.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0009000000-ed61090013f0dc5f5c5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0190000000-e9bcd2accdf5b7e40a88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0590000000-04b1d4265cb156217f40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0790000000-5c42b9a9a2cd0c4114aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0960000000-88822d2fb3e7c0cdc0b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-6b560941c92823b7901cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0109000000-1531c1e1630dcb42b497View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-53199cfe3b343ae81afdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0109000000-0e790a7e6032e51bfeb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kf-9800000000-64d39c4a4fcc7f8b6f47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kf-9700000000-e516356ce3eca65bece8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-6b560941c92823b7901cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zgi-1390000000-84c6bc70aefcd3758f31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f7o-6940000000-a424e26ecc7465229968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4m-0390000000-9b7253cd5718aa434e46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4m-0290000000-d88f8004205c7223aa9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01t9-0592000000-92a48c620c961fdb430fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0409000000-03f5678c6178e634f254View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-dcf68dbfd090c7fdfe11View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fluoxetine Metabolism PathwayPw000622Pw000622 greyscalePw000622 simpleNot Available
Fluoxetine PathwayPw000428Pw000428 greyscalePw000428 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00472 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00472 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00472
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluoxetine
NuGOwiki LinkHMDB0014615
METLIN IDNot Available
PubChem Compound3386
PDB IDNot Available
ChEBI ID5118
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wong DT, Horng JS, Bymaster FP, Hauser KL, Molloy BB: A selective inhibitor of serotonin uptake: Lilly 110140, 3-(p-trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine. Life Sci. 1974 Aug 1;15(3):471-9. [PubMed:4549929 ]
  2. Wong DT, Bymaster FP, Engleman EA: Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication. Life Sci. 1995;57(5):411-41. [PubMed:7623609 ]
  3. Carlsson A, Wong DT: Correction: a note on the discovery of selective serotonin reuptake inhibitors. Life Sci. 1997;61(12):1203. [PubMed:9315511 ]
  4. Caley CF: Extrapyramidal reactions and the selective serotonin-reuptake inhibitors. Ann Pharmacother. 1997 Dec;31(12):1481-9. [PubMed:9416386 ]
  5. Gerber PE, Lynd LD: Selective serotonin-reuptake inhibitor-induced movement disorders. Ann Pharmacother. 1998 Jun;32(6):692-8. [PubMed:9640489 ]