Identification

Name
Setiptiline
Accession Number
DB09304
Type
Small Molecule
Groups
Experimental
Description

Setiptiline is a tetracyclic antidepressant (TeCA) which acts as a noradrenergic and specific serotonergic antidepressant (NaSSA). It was launched in 1989 for the treatment of depression in Japan by Mochida.

Structure
Thumb
Synonyms
Not Available
External IDs
MO-8282 / Org 8282
Product Ingredients
IngredientUNIICASInChI Key
Setiptiline maleate9VOZ30EO2Y85650-57-3AVPIBVPBCWBXIU-BTJKTKAUSA-N
International/Other Brands
Tecipul
Categories
UNII
7L38105Z6E
CAS number
57262-94-9
Weight
Average: 261.368
Monoisotopic: 261.151749616
Chemical Formula
C19H19N
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

Pharmacology

Indication

For the treatment of depression [4].

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
Human
USerotonin Receptors
antagonist
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Setiptiline.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Setiptiline.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Setiptiline.
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Setiptiline.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Setiptiline.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Setiptiline.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Setiptiline.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Setiptiline.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Setiptiline.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Setiptiline.
Food Interactions
Not Available

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.
External Links
KEGG Drug
D08511
PubChem Compound
5205
PubChem Substance
310265193
ChemSpider
5016
ChEBI
135076
ChEMBL
CHEMBL2104895
Wikipedia
Setiptiline

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 Solubility0.0338 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

Taxonomy

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
Dibenzocycloheptene / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organoheterocyclic compound / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein group
Organism
Human
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
Human
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 November 02, 2018 08:49