NAV

(R)-Fluoxetine

Identification

Generic Name
(R)-Fluoxetine
DrugBank Accession Number
DB08472
Background

An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has R configuration (the antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine).

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 309.3261
Monoisotopic: 309.134048818
Chemical Formula
C17H18F3NO
Synonyms
  • (+)-fluoxetine
  • (R)-(+)-fluoxetine
  • (R)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine
  • (R)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine
  • (R)-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine
  • (R)-N-methyl-γ-(4-trifluoromethylphenoxy)-3-phenylpropylamine
  • (R)-Prozac
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Phenoxy compounds / Phenol ethers / Aralkylamines / Alkyl aryl ethers / Dialkylamines / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine (CHEBI:86991)
Affected organisms
Not Available

Chemical Identifiers

UNII
F279341RUQ
CAS number
100568-03-4
InChI Key
RTHCYVBBDHJXIQ-MRXNPFEDSA-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-/m1/s1
IUPAC Name
methyl[(3R)-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
PubChem Compound
1548970
PubChem Substance
99444943
ChemSpider
1265981
BindingDB
50136166
ChEBI
86991
ChEMBL
CHEMBL153036
ZINC
ZINC000001530638
PDBe Ligand
RFX
PDB Entries
3gwv / 4mm8

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Polarizability30.32 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9640000000-1b57c9c8e689aa1b7117
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9303000000-befa4649ed515eb63a92
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-0903000000-336450f4e92f0ad57203
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9310000000-494ba11edaf63292ecb9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-195ef0f5145ec1fd5c2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-4941000000-bd7eb2985b2a3cac0137
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-ed37087a0d3c8eb00ebf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-167.14053
predicted
DeepCCS 1.0 (2019)
[M+H]+169.49854
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.30453
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Transporter
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. [Article]

Drug created at September 15, 2010 21:32 / Updated at June 12, 2020 16:52