Identification

Name
Seproxetine
Accession Number
DB06731
Type
Small Molecule
Groups
Investigational
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
Product Ingredients
IngredientUNIICASInChI Key
Seproxetine hydrochlorideK4QYN23H2N127685-30-7GMTWWEPBGGXBTO-RSAXXLAASA-N
Categories
UNII
25CO3X0R31
CAS number
126924-38-7
Weight
Average: 295.305
Monoisotopic: 295.118398628
Chemical Formula
C16H16F3NO
InChI Key
WIQRCHMSJFFONW-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not 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.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

4-16 days

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Fluoxetine Action PathwayDrug action
Fluoxetine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3058751
PubChem Substance
99443277
ChemSpider
2319851
BindingDB
50254790
ChEMBL
CHEMBL465123
IUPHAR
208
Guide to Pharmacology
GtP Drug Page
HET
405
Wikipedia
Seproxetine
PDB Entries
4xdk

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 Solubility0.00915 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udr-4900000000-13da6a364a36d0fedd10
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0zg0-5900000000-a6b27f2345c200db07d6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0k9i-8900000000-c21cf411d87f738fcfa3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4r-9600000000-0c51b31ab1d7496940e5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4r-9600000000-1c81d9b3f0df4c3c5cd1

Taxonomy

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 / Organopnictogen compounds / Organofluorides / Monoalkylamines / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Trifluoromethylbenzene / Phenoxy compound / Phenol ether / Alkyl aryl ether / Aralkylamine / Ether / Organopnictogen compound / Primary amine / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not 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 un...
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 un...
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 November 09, 2017 03:55