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Showing drug card for Fluoxetine (DB00472)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:29
Primary Accession Number DB00472
Secondary Accession Number
  • APRD00530
Name Fluoxetine
Drug Type
  • Approved
  • Small Molecule
Description The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants. [PubChem]
Synonyms
  1. Fluoxetina [INN-Spanish]
  2. Fluoxetina [Spanish]
  3. Fluoxetine Hcl
  4. Fluoxetine Hydrochloride
  5. Fluoxetinum [INN-Latin]
Brand Names
  1. Adofen
  2. Animex-On
  3. Deprex
  4. Eufor
  5. Fluctin
  6. Fluoxeren
  7. Fluval
  8. Fontex
  9. Foxetin
  10. Portal
  11. Prozac
  12. Prozac Weekly
  13. Pulvules
  14. Reneuron
  15. Sarafem
Brand Mixtures Not Available
Chemical IUPAC Name N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
Chemical Formula C17H18F3NO
Chemical Structure Structure
CAS Registry Number 54910-89-3
InChI Identifier InChI=1/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 Key RTHCYVBBDHJXIQ-UHFFFAOYAV
KEGG Drug D00823 Link Image
KEGG Compound Not Available
PubChem Compound 3386 Link Image
PubChem Substance 181999 Link Image
ChEBI ID Not Available
PharmGKB ID PA449673 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02242124 Link Image
RxList Link http://www.rxlist.com/cgi/generic/fluoxetine.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Fluoxetine Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference B. B. Mally; K. K. Schmiegel; U.S. Pat. 4,314,081 (1982)
Average Molecular Weight 309.3261
Monoisotopic Molecular Weight 309.1340
State Solid
Melting Point 179-182oC
Experimental Water Solubility 50 mg/mL at 25°C Source: PhysProp
Predicted Water Solubility 1.70e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4.6 Source: PhysProp
Predicted LogP 4.10 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.26 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CNCC[C@H](OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Canonical SMILES CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Drug Category
  • Antidepressants, Second-Generation
  • Antidepressive Agents, Second-Generation
  • Selective Serotonin Reuptake Inhibitors (SSRIs)
  • Serotonin Uptake Inhibitors
ATC Codes
AHFS Codes
  • 28:16.04.20
Indication For the treatment of depression, obsessive compulsive disorder, and bulimia nervosa.
Pharmacology Fluoxetine, an antidepressant agent belonging to the selective serotonin reuptake inhibitors (SSRIs), is used to treat depression, bulimia nervosa, premenstrual dysphoric disorder, panic disorder and post-traumatic stress. According to the amines hypothesis, a functional decrease in the activity of amines, such as serotonin and norepinephrine, would result in depression; a functional increase of the activity of these amines would result in mood elevation. Fluoxetine's effects are thought to be associated with the inhibition of 5HT receptor, which leads to an increase of serotonin level.
Mechanism of Action Metabolized 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 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Absorption 72%
Toxicity Symptoms of overdose include agitation, restlessness, hypomania, and other signs of CNS excitation. LD50=284mg/kg (orally in mice).
Protein Binding 94.5%
Biotransformation Hepatic.
Half Life 1 to 3 days
Dosage Forms
Form Route
Capsule Oral
Liquid Oral
Solution Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The SSRI increases the effect of anticoagulant
Almotriptan Increased risk of CNS adverse effects
Amitriptyline Fluoxetine increases the effect and toxicity of tricyclics
Amoxapine Fluoxetine increases the effect and toxicity of tricyclics
Amphetamine Risk of serotoninergic syndrome
Anisindione The SSRI increases the effect of anticoagulant
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atomoxetine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
Benzphetamine Risk of serotoninergic syndrome
Carbamazepine Increases the effect of carbamazepine
Carvedilol The SSRI increases the effect of the beta-blocker
Cilostazol Increases the effect of cilostazol
Clarithromycin Possible serotoninergic syndrome with this combination
Clomipramine Fluoxetine increases the effect and toxicity of tricyclics
Clozapine The antidepressant increases the effect of clozapine
Cyclosporine The antidepressant increases the effect and toxicity of cyclosporine
Cyproheptadine Possible antagonism of action
Desipramine Fluoxetine increases the effect and toxicity of tricyclics
Dexfenfluramine Risk of serotoninergic syndrome
Dextroamphetamine Risk of serotoninergic syndrome
Dextromethorphan Combination associated with possible serotoninergic syndrome
Dicumarol The SSRI increases the effect of anticoagulant
Diethylpropion Risk of serotoninergic syndrome
Dihydroergotamine Possible ergotism and severe ischemia with this combination
Doxepin Fluoxetine increases the effect and toxicity of tricyclics
Eletriptan Increased risk of CNS adverse effects
Ergotamine Possible ergotism and severe ischemia with this combination
Erythromycin Possible serotoninergic syndrome with this combination
Ethotoin Fluoxetine increases the effect of phenytoin
Fenfluramine Risk of serotoninergic syndrome
Fosphenytoin Fluoxetine increases the effect of phenytoin
Frovatriptan Increased risk of CNS adverse effects
Imipramine Fluoxetine increases the effect and toxicity of tricyclics
Isocarboxazid Possible severe adverse reaction with this combination
Josamycin Possible serotoninergic syndrome with this combination
Linezolid Combination associated with possible serotoninergic syndrome
Lithium The SSRI increases serum levels of lithium
Mazindol Risk of serotoninergic syndrome
Mephenytoin Fluoxetine increases the effect of phenytoin
Mesoridazine Increased risk of cardiotoxicity and arrhythmias
Methamphetamine Risk of serotoninergic syndrome
Metoprolol The SSRI increases the effect of the beta-blocker
Moclobemide Risk of serotoninergic syndrome
Naratriptan Increased risk of CNS adverse effects
Nortriptyline Fluoxetine increases the effect and toxicity of tricyclics
Oxycodone Increased risk of serotonin syndrome
Phendimetrazine Risk of serotoninergic syndrome
Phenelzine Possible severe adverse reaction with this combination
Phentermine Risk of serotoninergic syndrome
Phenylpropanolamine Risk of serotoninergic syndrome
Phenytoin Fluoxetine increases the effect of phenytoin
Propafenone Increases the effect and toxicity of propafenone
Propranolol The SSRI increases the effect of the beta-blocker
Protriptyline Fluoxetine increases the effect and toxicity of tricyclics
Rasagiline Possible severe adverse reaction with this combination
Risperidone The SSRI increases the effect and toxicity of risperidone
Ritonavir Increased risk of serotonin syndrome
Rizatriptan Increased risk of CNS adverse effects
Selegiline Possible severe adverse reaction with this combination
Sibutramine Risk of serotoninergic syndrome
St. John's Wort St. John's Wort increases the effect and toxicity of the SSRI
Sumatriptan Increased risk of CNS adverse effects
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Thioridazine Increased risk of cardiotoxicity and arrhythmias
Tramadol Increased risk of serotonin syndrome
Tranylcypromine Possible severe adverse reaction with this combination
Trimipramine Fluoxetine increases the effect and toxicity of tricyclics
Troleandomycin Possible serotoninergic syndrome with this combination
Warfarin The SSRI increases the effect of anticoagulant
Zolmitriptan Increased risk of CNS adverse effects
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation and nausea.
Pathways 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 Link Image]
  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 Link Image]
  3. Carlsson A, Wong DT: Correction: a note on the discovery of selective serotonin reuptake inhibitors. Life Sci. 1997;61(12):1203. [PubMed Link Image]
  4. Caley CF: Extrapyramidal reactions and the selective serotonin-reuptake inhibitors. Ann Pharmacother. 1997 Dec;31(12):1481-9. [PubMed Link Image]
  5. Gerber PE, Lynd LD: Selective serotonin-reuptake inhibitor-induced movement disorders. Ann Pharmacother. 1998 Jun;32(6):692-8. [PubMed Link Image]
  6. Drugs.com Link Image
  7. Wikipedia Link Image
  8. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C9 (CYP2C9)
Targets
  1. Sodium-dependent serotonin transporter
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C9 (CYP2C9)
Enzyme 1 Gene Name CYP2C9
Enzyme 1 SwissProt ID P11712 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P11712|CP2C9_HUMAN Cytochrome P450 2C9 (EC 1.14.13.80) 
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV
YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM
KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID
LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK
KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 824
Target 1 Name Sodium-dependent serotonin transporter
Target 1 Synonyms
  1. 5HT transporter
  2. 5HTT
Target 1 Gene Name SLC6A4
Target 1 Protein Sequence >Sodium-dependent serotonin transporter 
METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAVPSPGAGDDTR
HSIPATTTTLVAELHQGERETWGKKVDFLLSVIGYAVDLGNVWRFPYICYQNGGGAFLLP
YTIMAIFGGIPLFYMELALGQYHRNGCISIWRKICPIFKGIGYAICIIAFYIASYYNTIM
AWALYYLISSFTDQLPWTSCKNSWNTGNCTNYFSEDNITWTLHSTSPAEEFYTRHVLQIH
RSKGLQDLGGISWQLALCIMLIFTVIYFSIWKGVKTSGKVVWVTATFPYIILSVLLVRGA
TLPGAWRGVLFYLKPNWQKLLETGVWIDAAAQIFFSLGPGFGVLLAFASYNKFNNNCYQD
ALVTSVVNCMTSFVSGFVIFTVLGYMAEMRNEDVSEVAKDAGPSLLFITYAEAIANMPAS
TFFAIIFFLMLITLGLDSTFAGLEGVITAVLDEFPHVWAKRRERFVLAVVITCFFGSLVT
LTFGGAYVVKLLEEYATGPAVLTVALIEAVAVSWFYGITQFCRDVKEMLGFSPGWFWRIC
WVAISPLFLLFIICSFLMSPPQLRLFQYNYPYWSIILGYCIGTSSFICIPTYIAYRLIIT
PGTFKERIIKSITPETPTEIPCGDIRLNAV
Target 1 Number of Residues 640
Target 1 Molecular Weight 70325
Target 1 Theoretical pI 6.17
Target 1 GO Classification
Function
transporter activity
neurotransmitter transporter activity
neurotransmitter:sodium symporter activity
Process
physiological process
cellular physiological process
transport
neurotransmitter transport
Component
cell
membrane
intrinsic to membrane
integral to membrane
integral to plasma membrane
Target 1 General Function Involved in serotonin:sodium symporter activity
Target 1 Specific Function Terminates the action of serotonine by its high affinity sodium-dependent reuptake into presynaptic terminals
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 88-108
  • 116-135
  • 160-180
  • 253-271
  • 280-297
  • 333-350
  • 362-383
  • 417-436
  • 464-482
  • 498-518
  • 539-558
  • 577-595
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 36433 Link Image
Target 1 UniProtKB/Swiss-Prot ID P31645 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name SC6A4_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1893 bp 
ATGGAGACGACGCCCTTGAATTCTCAGAAGCAGCTATCAGCGTGTGAAGATGGAGAAGAT
TGTCAGGAAAACGGAGTTCTACAGAAGGTTGTTCCCACCCCAGGGGACAAAGTGGAGTCC
GGGCAAATATCCAATGGGTACTCAGCAGTTCCAAGTCCTGGTGCGGGAGATGACACACGG
CACTCTATCCCAGCGACCACCACCACCCTAGTGGCTGAGCTTCATCAAGGGGAACGGGAG
ACCTGGGGCAAGAAGGTGGATTTCCTTCTCTCAGTGATTGGCTATGCTGTGGACCTGGGC
AATGTCTGGCGCTTCCCCTACATATGTTACCAGAATGGAGGGGGGGCATTCCTCCTCCCC
TACACCATCATGGCCATTTTTGGGGGAATCCCGCTCTTTTACATGGAGCTCGCACTGGGA
CAGTACCACCGAAATGGATGCATTTCAATATGGAGGAAAATCTGCCCGATTTTCAAAGGG
ATTGGTTATGCCATCTGCATCATTGCCTTTTACATTGCTTCCTACTACAACACCATCATG
GCCTGGGCGCTATACTACCTCATCTCCTCCTTCACGGACCAGCTGCCCTGGACCAGCTGC
AAGAACTCCTGGAACACTGGCAACTGCACCAATTACTTCTCCGAGGACAACATCACCTGG
ACCCTCCATTCCACGTCCCCTGCTGAAGAATTTTACACGCGCCACGTCCTGCAGATCCAC
CGGTCTAAGGGGCTCCAGGACCTGGGGGGCATCAGCTGGCAGCTGGCCCTCTGCATCATG
CTGATCTTCACTGTTATCTACTTCAGCATCTGGAAAGGCGTCAAGACCTCTGGCAAGGTG
GTGTGGGTGACAGCCACCTTCCCTTATATCATCCTTTCTGTCCTGCTGGTGAGGGGTGCC
ACCCTCCCTGGAGCCTGGAGGGGTGTTCTCTTCTACTTGAAACCCAATTGGCAGAAACTC
CTGGAGACAGGGGTGTGGATAGATGCAGCCGCTCAGATCTTCTTCTCTCTTGGTCCGGGC
TTTGGGGTCCTGCTGGCTTTTGCTAGCTACAACAAGTTCAACAACAACTGCTACCAAGAT
GCCCTGGTGACCAGCGTGGTGAACTGCATGACGAGCTTCGTTTCGGGATTTGTCATCTTC
ACAGTGCTCGGTTACATGGCTGAGATGAGGAATGAAGATGTGTCTGAGGTGGCCAAAGAC
GCAGGTCCCAGCCTCCTCTTCATCACGTATGCAGAAGCGATAGCCAACATGCCAGCGTCC
ACTTTCTTTGCCATCATCTTCTTTCTGATGTTAATCACGCTGGGCTTGGACAGCACGTTT
GCAGGCTTGGAGGGGGTGATCACGGCTGTGCTGGATGAGTTCCCACACGTCTGGGCCAAG
CGCCGGGAGCGGTTCGTGCTCGCCGTGGTCATCACCTGCTTCTTTGGATCCCTGGTCACC
CTGACTTTTGGAGGGGCCTACGTGGTGAAGCTGCTGGAGGAGTATGCCACGGGGCCCGCA
GTGCTCACTGTCGCGCTGATCGAAGCAGTCGCTGTGTCTTGGTTCTATGGCATCACTCAG
TTCTGCAGGGACGTGAAGGAAATGCTCGGCTTCAGCCCGGGGTGGTTCTGGAGGATCTGC
TGGGTGGCCATCAGCCCTCTGTTTCTCCTGTTCATCATTTGCAGTTTTCTGATGAGCCCG
CCACAACTACGACTTTTCCAATATAATTATCCTTACTGGAGTATCATCTTGGGTTACTGC
ATAGGAACCTCATCTTTCATTTGCATCCCCACATATATAGCTTATCGGTTGATCATCACT
CCAGGGACATTTAAAGAGCGTATTATTAAAAGTATTACCCCGGAGACACCAACAGAAATT
CCTTGTGGGGACATCCGCTTGAATGCTGTGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID SLC6A4 Link Image
Target 1 GenAtlas ID SLC6A4 Link Image
Target 1 HGNC ID HGNC:11050 Link Image
Target 1 Chromosome Location 17
Target 1 Locus 17q11.1-q12
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cargill M, Altshuler D, Ireland J, Sklar P, Ardlie K, Patil N, Shaw N, Lane CR, Lim EP, Kalyanaraman N, Nemesh J, Ziaugra L, Friedland L, Rolfe A, Warrington J, Lipshutz R, Daley GQ, Lander ES: Characterization of single-nucleotide polymorphisms in coding regions of human genes. Nat Genet. 1999 Jul;22(3):231-8. [PubMed Link Image]
  2. Caspi A, Sugden K, Moffitt TE, Taylor A, Craig IW, Harrington H, McClay J, Mill J, Martin J, Braithwaite A, Poulton R: Influence of life stress on depression: moderation by a polymorphism in the 5-HTT gene. Science. 2003 Jul 18;301(5631):386-9. [PubMed Link Image]
  3. Ramamoorthy S, Bauman AL, Moore KR, Han H, Yang-Feng T, Chang AS, Ganapathy V, Blakely RD: Antidepressant- and cocaine-sensitive human serotonin transporter: molecular cloning, expression, and chromosomal localization. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2542-6. [PubMed Link Image]
  4. Lesch KP, Wolozin BL, Murphy DL, Reiderer P: Primary structure of the human platelet serotonin uptake site: identity with the brain serotonin transporter. J Neurochem. 1993 Jun;60(6):2319-22. [PubMed Link Image]
  5. Lesch KP, Wolozin BL, Estler HC, Murphy DL, Riederer P: Isolation of a cDNA encoding the human brain serotonin transporter. J Neural Transm Gen Sect. 1993;91(1):67-72. [PubMed Link Image]
Target 1 Drug References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  2. Richman A, Heinrichs SC: Seizure prophylaxis in an animal model of epilepsy by dietary fluoxetine supplementation. Epilepsy Res. 2007 Apr;74(1):19-27. Epub 2007 Jan 9. [PubMed Link Image]
  3. Iceta R, Mesonero JE, Alcalde AI: Effect of long-term fluoxetine treatment on the human serotonin transporter in Caco-2 cells. Life Sci. 2007 Mar 27;80(16):1517-24. Epub 2007 Jan 20. [PubMed Link Image]
  4. Mirza NR, Nielsen EO, Troelsen KB: Serotonin transporter density and anxiolytic-like effects of antidepressants in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2007 May 9;31(4):858-66. Epub 2007 Jan 30. [PubMed Link Image]
  5. Sanders AC, Hussain AJ, Hen R, Zhuang X: Chronic Blockade or Constitutive Deletion of the Serotonin Transporter Reduces Operant Responding for Food Reward. Neuropsychopharmacology. 2007 Mar 14;. [PubMed Link Image]
  6. Goren MZ, Kucukibrahimoglu E, Berkman K, Terzioglu B: Fluoxetine partly exerts its actions through GABA: a neurochemical evidence. Neurochem Res. 2007 Sep;32(9):1559-65. Epub 2007 May 8. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.