(S)-Fluoxetine

Identification

Name
(S)-Fluoxetine
Accession Number
DB08544
Type
Small Molecule
Groups
Experimental
Description

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).

Structure
Thumb
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
Categories
Not Available
UNII
6MYD4C025Q
CAS number
100568-02-3
Weight
Average: 309.3261
Monoisotopic: 309.134048818
Chemical Formula
C17H18F3NO
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[[email protected]](OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTransporterNot AvailableAquifex aeolicus (strain VF5)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
1548968
PubChem Substance
99445015
ChemSpider
1265979
BindingDB
81875
ChEBI
86992
ChEMBL
CHEMBL1169388
HET
SFX
PDB Entries
3gww

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.0017 mg/mLALOGPS
logP4.09ALOGPS
logP4.17ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.37 m3·mol-1ChemAxon
Polarizability30.34 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.983
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5899
P-glycoprotein inhibitor IInhibitor0.8565
P-glycoprotein inhibitor IIInhibitor0.5459
Renal organic cation transporterInhibitor0.5633
CYP450 2C9 substrateNon-substrate0.7475
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5754
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7149
Ames testNon AMES toxic0.7105
CarcinogenicityNon-carcinogens0.8089
BiodegradationNot ready biodegradable0.9868
Rat acute toxicity2.6048 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6058
hERG inhibition (predictor II)Inhibitor0.8467
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

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
  1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:32 / Updated on December 01, 2017 16:06