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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014615
Secondary Accession Numbers
  • HMDB14615
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 lead 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. Fluoxetine 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
Data?1582753199
Synonyms
ValueSource
SarafemChEMBL, HMDB, MeSH
SymbyaxChEMBL, HMDB
ProzacChEMBL, HMDB, MeSH
Fluoxetine hydrochlorideMeSH, HMDB
N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamineMeSH, HMDB
FluoxetinMeSH, HMDB
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point179 - 182 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0017 g/LNot Available
LogP4.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM176.530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP4.09ALOGPS
logP4.17ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.37 m³·mol⁻¹ChemAxon
Polarizability30.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+173.330932474
DeepCCS[M-H]-170.94230932474
DeepCCS[M-2H]-203.82830932474
DeepCCS[M+Na]+179.39330932474
AllCCS[M+H]+171.632859911
AllCCS[M+H-H2O]+168.232859911
AllCCS[M+NH4]+174.732859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-172.432859911
AllCCS[M+Na-2H]-172.032859911
AllCCS[M+HCOO]-171.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FluoxetineCNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C12308.6Standard polar33892256
FluoxetineCNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C11900.2Standard non polar33892256
FluoxetineCNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C11885.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluoxetine,1TMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C2111.1Semi standard non polar33892256
Fluoxetine,1TMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C2046.4Standard non polar33892256
Fluoxetine,1TMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C2338.0Standard polar33892256
Fluoxetine,1TBDMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2315.2Semi standard non polar33892256
Fluoxetine,1TBDMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2235.5Standard non polar33892256
Fluoxetine,1TBDMS,isomer #1CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2453.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9530000000-45c870b2463186b9230c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-dcf68dbfd090c7fdfe112014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-qTof , Positive-QTOFsplash10-01t9-0592000000-92a48c620c961fdb430f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOFsplash10-03di-0009000000-ed61090013f0dc5f5c5a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOFsplash10-014i-0190000000-e9bcd2accdf5b7e40a882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOFsplash10-014i-0590000000-04b1d4265cb156217f402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOFsplash10-014i-0790000000-5c42b9a9a2cd0c4114aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0960000000-88822d2fb3e7c0cdc0b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-6b560941c92823b7901c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-03di-0109000000-1531c1e1630dcb42b4972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0006-9000000000-53199cfe3b343ae81afd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-03di-0109000000-0e790a7e6032e51bfeb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-00kf-9800000000-64d39c4a4fcc7f8b6f472017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-00kf-9700000000-e516356ce3eca65bece82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-6b560941c92823b7901c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0zgi-1390000000-84c6bc70aefcd3758f312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0f7o-6940000000-a424e26ecc74652299682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0a4m-0390000000-9b7253cd5718aa434e462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOFsplash10-0a4m-0290000000-d88f8004205c7223aa9f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine , positive-QTOFsplash10-01t9-0592000000-92a48c620c961fdb430f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluoxetine LC-ESI-QFT , positive-QTOFsplash10-03di-0409000000-03f5678c6178e634f2542017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 10V, Positive-QTOFsplash10-03fr-1179000000-9f0773309b13bac8c3042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 20V, Positive-QTOFsplash10-0h03-5292000000-1e7d8430611731d4e4a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 40V, Positive-QTOFsplash10-0006-9830000000-b2a37ff34ba2d39749892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 10V, Negative-QTOFsplash10-0a4i-1009000000-113c9621ae90d769ee332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 20V, Negative-QTOFsplash10-0a4i-3469000000-4480faded690242a155c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluoxetine 40V, Negative-QTOFsplash10-03di-2910000000-2c7cf659d217661ff8972016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00472 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00472 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3386
PDB IDNot Available
ChEBI ID86990
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]