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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
SynonymLanguageCode
(S)-norfluoxetineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Seproxetine Hydrochloride
Thumb
  • InChI Key: WIQRCHMSJFFONW-UHFFFAOYNA-N
  • Monoisotopic Mass: 295.118398754
  • Average Mass: 295.2995
DBSALT000562
CategoriesNot Available
CAS number126924-38-7
WeightAverage: 295.2995
Monoisotopic: 295.118398754
Chemical FormulaC16H16F3NO
InChI KeyWIQRCHMSJFFONW-UHFFFAOYSA-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
IUPAC Name
3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
SMILES
NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Taxonomy
ClassificationNot classified
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionSeproxetine, 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life4-16 days
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Fluoxetine Metabolism PathwayDrug metabolismSMP00646
Fluoxetine Action PathwayDrug actionSMP00426
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7122
CYP450 2D6 substrateInhibitor0.634
CYP450 2C19 substrateInhibitor0.8499
CYP450 3A4 substrateInhibitor0.6346
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
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
Polarizability28.13 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

2. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

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Drug created on August 18, 2010 14:54 / Updated on September 16, 2013 18:04