Identification
NameSeproxetine
Accession NumberDB06731
TypeSmall Molecule
GroupsInvestigational
Description

Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is an active metabolite of fluoxetine. Seproxetine was being investigated by Eli Lilly as an antidepressant but development was never completed and the drug was never marketed.

Structure
Thumb
Synonyms
(S)-norfluoxetine
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Seproxetine hydrochlorideK4QYN23H2N 127685-30-7GMTWWEPBGGXBTO-RSAXXLAASA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNII25CO3X0R31
CAS number126924-38-7
WeightAverage: 295.305
Monoisotopic: 295.118398628
Chemical FormulaC16H16F3NO
InChI KeyWIQRCHMSJFFONW-HNNXBMFYSA-N
InChI
InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2/t15-/m0/s1
IUPAC Name
(3S)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
SMILES
NCC[[email protected]](OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is an active metabolite of fluoxetine. Seproxetine was being investigated by Eli Lilly as an antidepressant but development was never completed and the drug was never marketed.

Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life

4-16 days

ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Fluoxetine Action PathwayDrug actionSMP00426
Fluoxetine Metabolism PathwayDrug metabolismSMP00646
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00915 mg/mLALOGPS
logP3.8ALOGPS
logP3.74ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.25 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity75.59 m3·mol-1ChemAxon
Polarizability28.15 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+0.9778
Caco-2 permeable+0.7535
P-glycoprotein substrateNon-substrate0.675
P-glycoprotein inhibitor IInhibitor0.8106
P-glycoprotein inhibitor IIInhibitor0.5156
Renal organic cation transporterNon-inhibitor0.5059
CYP450 2C9 substrateNon-substrate0.853
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.5776
CYP450 1A2 substrateInhibitor0.8745
CYP450 2C9 inhibitorNon-inhibitor0.7122
CYP450 2D6 inhibitorInhibitor0.634
CYP450 2C19 inhibitorInhibitor0.8499
CYP450 3A4 inhibitorInhibitor0.6346
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8823
Ames testNon AMES toxic0.5993
CarcinogenicityNon-carcinogens0.7532
BiodegradationNot ready biodegradable0.9893
Rat acute toxicity2.5035 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6152
hERG inhibition (predictor II)Inhibitor0.8112
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udr-4900000000-13da6a364a36d0fedd10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0zg0-5900000000-a6b27f2345c200db07d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0k9i-8900000000-c21cf411d87f738fcfa3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-9600000000-0c51b31ab1d7496940e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-9600000000-1c81d9b3f0df4c3c5cd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative ParentsPhenoxy compounds / Phenol ethers / Aralkylamines / Alkyl aryl ethers / Organofluorides / Monoalkylamines / Hydrocarbon derivatives / Alkyl fluorides
SubstituentsTrifluoromethylbenzene / Phenoxy compound / Phenol ether / Alkyl aryl ether / Aralkylamine / Ether / Organic nitrogen compound / Primary amine / Hydrocarbon derivative / Organooxygen compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Uniprot Name:
Cytochrome P450 3A5
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Uniprot Name:
Cytochrome P450 3A7
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Drug created on August 18, 2010 14:54 / Updated on September 01, 2017 11:30