fluoxetine   

GtoPdb Ligand ID: 203

Synonyms: Prozac®
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
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1987))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
International Nonproprietary Names
INN number INN
3883 fluoxetine
Synonyms
Prozac®
Database Links
BindingDB Ligand 30130
CAS Registry No. 54910-89-3
ChEBI CHEBI:5118
ChEMBL Ligand CHEMBL41
DrugBank Ligand DB00472
DrugCentral Ligand 1209
GtoPdb PubChem SID 135650270
PubChem CID 3386
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Wikipedia Fluoxetine