fluoxetine   Click here for help

GtoPdb Ligand ID: 203

Synonyms: Prozac®
Approved drug
fluoxetine is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: The approved drug fluoxetine is a racemic mixture of two enantiomers; (R)-fluoxetine and (S)-Fluoxetine. The structure shown here does not specify stereochemistry and represents the mixture. The two PDB links listed above represent the two enantiomers. Fluoxetine is metabolised in the body to active metabolite norfluoxetine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 21.26
Molecular weight 309.13
XLogP 4.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
Isomeric SMILES CNCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
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
InChI Key RTHCYVBBDHJXIQ-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2C receptor Rn Antagonist Antagonist 7.3 pKi - 9
pKi 7.3 [9]
5-HT2A receptor Rn Antagonist Antagonist 6.5 pKi - 9
pKi 6.5 [9]
5-HT6 receptor Rn Antagonist Antagonist 5.8 pKi - 6
pKi 5.8 [6]
5-HT2B receptor Hs Antagonist Antagonist 5.3 pKi - 9
pKi 5.3 [9]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv3.1 Rn Gating inhibitor - 6.1 pIC50 - 2
pIC50 6.1 [2]
Kir3.2 Mm Gating inhibitor Antagonist 4.1 – 4.8 pIC50 - 5
pIC50 4.1 – 4.8 [5]
Voltage: -70.0 mV
CaCC Hs Channel blocker - - - -
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
SERT Primary target of this compound Hs Inhibitor Inhibition 8.5 pKi - 10
pKi 8.5 (Ki 3x10-9 M) [10]
Plasma membrane monoamine transporter Hs Inhibitor Inhibition 4.6 pKi - 3,11
pKi 4.6 (Ki 2.27x10-5 M) [3,11]