(S)-Fluoxetine
Identification
- Generic Name
- (S)-Fluoxetine
- DrugBank Accession Number
- DB08544
- Background
An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has S configuration (the antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine).
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (S)-Fluoxetine (DB08544)
- Weight
- Average: 309.3261
Monoisotopic: 309.134048818 - Chemical Formula
- C17H18F3NO
- Synonyms
- (−)-fluoxetine
- (S)-(−)-fluoxetine
- (S)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine
- (S)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine
- (S)-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine
- (S)-N-methyl-γ-(4-trifluoromethylphenoxy)-3-phenylpropylamine
- (S)-Prozac
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTransporter Not Available Aquifex aeolicus (strain VF5) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6MYD4C025Q
- CAS number
- 100568-02-3
- InChI Key
- RTHCYVBBDHJXIQ-INIZCTEOSA-N
- 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/t16-/m0/s1
- IUPAC Name
- methyl[(3S)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amine
- SMILES
- CNCC[C@H](OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 1548968
- PubChem Substance
- 99445015
- ChemSpider
- 1265979
- BindingDB
- 81875
- ChEBI
- 86992
- ChEMBL
- CHEMBL1169388
- ZINC
- ZINC000001530637
- PDBe Ligand
- SFX
- PDB Entries
- 3gww / 6s3a / 6t3w
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0017 mg/mL ALOGPS logP 4.09 ALOGPS logP 4.17 ChemAxon logS -5.3 ALOGPS pKa (Strongest Basic) 9.8 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 21.26 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 80.37 m3·mol-1 ChemAxon Polarizability 30.34 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.983 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.5899 P-glycoprotein inhibitor I Inhibitor 0.8565 P-glycoprotein inhibitor II Inhibitor 0.5459 Renal organic cation transporter Inhibitor 0.5633 CYP450 2C9 substrate Non-substrate 0.7475 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.5754 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7149 Ames test Non AMES toxic 0.7105 Carcinogenicity Non-carcinogens 0.8089 Biodegradation Not ready biodegradable 0.9868 Rat acute toxicity 2.6048 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6058 hERG inhibition (predictor II) Inhibitor 0.8467
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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- Kind
- Protein
- Organism
- Aquifex aeolicus (strain VF5)
- Pharmacological action
- Unknown
- General Function
- Neurotransmitter:sodium symporter activity
- Specific Function
- Not Available
- Gene Name
- snf
- Uniprot ID
- O67854
- Uniprot Name
- Transporter
- Molecular Weight
- 57407.51 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created on September 15, 2010 21:32 / Updated on June 12, 2020 16:52