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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
Salts
Name/CAS Structure Properties
Seproxetine Hydrochloride
Thumb
  • InChI Key: WIQRCHMSJFFONW-UHFFFAOYNA-N
  • Monoisotopic Mass: 295.118398754
  • Average Mass: 295.2995
DBSALT000562
Brand namesNot Available
Brand mixturesNot Available
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
1-(3-amino-1-phenylpropoxy)-4-(trifluoromethyl)benzene
SMILES
NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylpropylamines
Direct parentPhenylpropylamines
Alternative parentsBenzylethers; Phenol Ethers; Alkyl Aryl Ethers; Polyamines; Organofluorides; Alkyl Fluorides; Monoalkylamines
Substituentsphenol ether; alkyl aryl ether; polyamine; ether; organohalogen; primary amine; organofluoride; primary aliphatic amine; amine; alkyl halide; alkyl fluoride; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9778
Caco-2 permeable + 0.7535
P-glycoprotein substrate Non-substrate 0.675
P-glycoprotein inhibitor I Inhibitor 0.8106
P-glycoprotein inhibitor II Inhibitor 0.5156
Renal organic cation transporter Non-inhibitor 0.5059
CYP450 2C9 substrate Non-substrate 0.853
CYP450 2D6 substrate Substrate 0.8919
CYP450 3A4 substrate Non-substrate 0.5776
CYP450 1A2 substrate Inhibitor 0.8745
CYP450 2C9 substrate Non-inhibitor 0.7122
CYP450 2D6 substrate Inhibitor 0.634
CYP450 2C19 substrate Inhibitor 0.8499
CYP450 3A4 substrate Inhibitor 0.6346
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8823
Ames test Non AMES toxic 0.5993
Carcinogenicity Non-carcinogens 0.7532
Biodegradation Not ready biodegradable 0.9893
Rat acute toxicity 2.5035 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6152
hERG inhibition (predictor II) Inhibitor 0.8112
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility9.15e-03 g/lALOGPS
logP3.8ALOGPS
logP3.74ChemAxon
logS-4.5ALOGPS
pKa (strongest basic)9.77ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area35.25ChemAxon
rotatable bond count6ChemAxon
refractivity75.59ChemAxon
polarizability28.13ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound4541
PubChem Substance99443277
ChemSpider4382
IUPHAR208
Guide to Pharmacology208
WikipediaSeproxetine
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