Setiptiline

Identification

Name
Setiptiline
Accession Number
DB09304
Description

Setiptiline is a tetracyclic antidepressant (TeCA) which acts as a noradrenergic and specific serotonergic antidepressant (NaSSA). In Japan, the company Mochida started its commercialization for the treatment of depression started in 1989.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 261.368
Monoisotopic: 261.151749616
Chemical Formula
C19H19N
Synonyms
  • Setiptilina
  • Setiptiline
  • Setiptilinum
External IDs
  • MO-8282
  • Org 8282

Pharmacology

Indication

For the treatment of depression 4.

Contraindications & Blackbox Warnings
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Pharmacodynamics

Setiptiline is a tertacyclic antidepressant 4. It acts to reduce the symptoms of major depressive disorder.

Mechanism of action

Setiptiline is an antagonist at the α2 adrenergic receptor and at serotonin receptors 3. The antagonism of the α2 receptors likely relieves presynaptic inhibition of adrenergic neurotransmission, allowing for greater and longer sustained release of noradrenaline into the synapse. The antagonism of serotonin receptors may produce an upregulation of the receptors leading to an eventual increase in serotonergic signalling. The actual physiological mechanisms behind the antidepressant effect of setiptiline is unknown but the listed possibilities exist as likely explanations.

TargetActionsOrganism
UAlpha-2 adrenergic receptors
antagonist
Humans
USerotonin Receptors
antagonist
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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.
DrugInteraction
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Setiptiline.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Setiptiline.
LevothyroxineThe risk or severity of adverse effects can be increased when Levothyroxine is combined with Setiptiline.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Setiptiline.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Setiptiline.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Setiptiline.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Setiptiline.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Setiptiline.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Setiptiline.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Setiptiline.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Setiptiline maleate9VOZ30EO2Y85650-57-3AVPIBVPBCWBXIU-BTJKTKAUSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Dibenzocycloheptenes
Sub Class
Not Available
Direct Parent
Dibenzocycloheptenes
Alternative Parents
Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aromatic heteropolycyclic compound / Azacycle / Dibenzocycloheptene / Hydrocarbon derivative / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound / Tertiary aliphatic amine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
7L38105Z6E
CAS number
57262-94-9
InChI Key
GVPIXRLYKVFFMK-UHFFFAOYSA-N
InChI
InChI=1S/C19H19N/c1-20-11-10-18-16-8-4-2-6-14(16)12-15-7-3-5-9-17(15)19(18)13-20/h2-9H,10-13H2,1H3
IUPAC Name
4-methyl-4-azatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),2(7),8,10,12,15,17-heptaene
SMILES
CN1CCC2=C(C1)C1=CC=CC=C1CC1=CC=CC=C21

References

General References
  1. Niho T, Ito C, Shibutani Y, Hashizume H, Yamaguchi K: [Pharmacological properties of MO-8282, a novel antidepressant]. Nihon Yakurigaku Zasshi. 1986 Oct;88(4):309-20. [PubMed:3792961]
  2. Przegalinski E, Baran L, Siwanowicz J, Rawlow A: The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282. Pol J Pharmacol Pharm. 1986 Jul-Aug;38(4):377-84. [PubMed:3774630]
  3. Tohda M, Takasu T, Nomura Y: Effects of antidepressants on serotonin-evoked current in Xenopus oocytes injected with rat brain mRNA. Eur J Pharmacol. 1989 Jul 4;166(1):57-63. [PubMed:2806365]
  4. Kamimura M, Aoba A: Drug Therapy for Depression in Japan. JMAJ. 2002 Jan;45(1):28-33.
KEGG Drug
D08511
PubChem Compound
5205
PubChem Substance
310265193
ChemSpider
5016
ChEBI
135076
ChEMBL
CHEMBL2104895
ZINC
ZINC000001482169
Wikipedia
Setiptiline

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 Solubility0.0338 mg/mLALOGPS
logP3.96ALOGPS
logP3.98ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.53 m3·mol-1ChemAxon
Polarizability30.49 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

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

Targets

Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Components:
References
  1. Katsuda Y: Monoamine interaction —Effects of long-term treatments with L-tryptophan and setiptiline maleate on rat brain α2- and β-adrenergic receptor— Kawasaki Med J. 1991;17(1-4):37-45.
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...

Components:
References
  1. Tohda M, Takasu T, Nomura Y: Effects of antidepressants on serotonin-evoked current in Xenopus oocytes injected with rat brain mRNA. Eur J Pharmacol. 1989 Jul 4;166(1):57-63. [PubMed:2806365]

Drug created on November 12, 2015 09:07 / Updated on June 12, 2020 10:52

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