MIANSERIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H20N2
Molecular Weight	264.3648
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN2C(C1)C3=C(CC4=C2C=CC=C4)C=CC=C3

InChI

InChIKey=UEQUQVLFIPOEMF-UHFFFAOYSA-N

InChI=1S/C18H20N2/c1-19-10-11-20-17-9-5-3-7-15(17)12-14-6-2-4-8-16(14)18(20)13-19/h2-9,18H,10-13H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB06148
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15771415 | http://www.medicines.org.au/files/mkptolvo.pdf

Mianserin is a tetracyclic antidepressant used for the treatment of depression. It was investigated as an adjuvant for reduction of negative and cognitive symptoms of schizophrenia, as an aid for opioid detoxification therapy (where it reduced symptoms but lead to higher drop-out rate), and for the treatment of post-traumatic stress disorder (where it was ineffective). Mianserin has a broad spectrum of activity with the most potent binding to 5-HT2A, 5-HT2C, H1, alpha2A and alpha2C receptor.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2778	4.3 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2778	4.4 nM [Ki]
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2778	1.7 nM [Ki]
Alpha-2a adrenergic receptor 63 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2778	4.8 nM [Ki]
Alpha-2c adrenergic receptor 37 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2778	3.8 nM [Ki]
Norepinephrine transporter 191 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Inhibitor 8297	101.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 235 Sources: http://www.medicines.org.au/files/mkptolvo.pdf	Primary	Approved 8429	TOVLON Approved Use For the treatment of major depression.
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12650957	Palliative	Phase IV 63	Unknown Approved Use Unknown
Opioid dependence 21 Sources: http://www.medicines.org.au/files/mkptolvo.pdf	Palliative	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Meta-analytical studies on new antidepressants.	2001	11719915
Effects of mirtazapine on the levels of exogenous histamine in the plasma of the cat.	2001	11678342
Tianeptine: a review of its use in depressive disorders.	2001	11463130
Do some antidepressants work faster than others?	2001	11444763
Pharmacology of rapid-onset antidepressant treatment strategies.	2001	11444761
Evidence of early onset of antidepressant effect in randomized controlled trials.	2001	11229783
Mirtazapine and bone marrow suppression: a case report.	2001 Aug	11555082
m-CPP hypolocomotion is selectively antagonized by compounds with high affinity for 5-HT(2C) receptors but not 5-HT(2A) or 5-HT(2B) receptors.	2001 Dec	11856898
A naturalistic open-label study of mirtazapine in autistic and other pervasive developmental disorders.	2001 Fall	11642476
Inhibition of stress- or anxiogenic-drug-induced increases in dopamine release in the rat prefrontal cortex by long-term treatment with antidepressant drugs.	2001 Feb	11181840
Serotonergic mechanism in imipramine induced antinociception in rat tail flick test.	2001 Jan	11211562
Serotonin-based pharmacotherapy for acute neuroleptic-induced akathisia: a new approach to an old problem.	2001 Jul	11435260
A placebo-controlled, crossover trial of granisetron in SRI-induced sexual dysfunction.	2001 Jun	11465525
Efficacy and safety of mirtazapine in major depressive disorder patients after SSRI treatment failure: an open-label trial.	2001 Jun	11465517
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.	2001 Jun	11459121
Discovery of a novel member of the histamine receptor family.	2001 Mar	11179435
[Depressive disorders. A third have a chronic course].	2001 May 28	11434274
Peripheral edema associated with mirtazapine.	2001 Nov	11724109
The effect of mirtazapine in panic disorder: an open label pilot study with a single-blind placebo run-in period.	2001 Nov	11712626
Trait anxiety and the effect of a single high dose of diazepam in unipolar depression.	2001 Nov-Dec	11684140
Fluvoxamine augmentation increases serum mirtazapine concentrations three- to fourfold.	2001 Oct	11675851
Prevention of the stress-induced increase in frontal cortical dopamine efflux of freely moving rats by long-term treatment with antidepressant drugs.	2001 Oct	11597820
Antidepressant drug treatments induce glial cell line-derived neurotrophic factor (GDNF) synthesis and release in rat C6 glioblastoma cells.	2001 Oct	11595754
Treatment of mood-congruent psychotic depression with imipramine.	2001 Oct	11578669
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001 Oct	11561066
Mirtazapine for treatment of depression and comorbidities in Alzheimer disease.	2001 Sep	11573849
[Toxicological analysis in the dawn of the third millenium].	2001 Sep-Oct	11602391
Mania associated with mirtazapine augmentation of fluoxetine.	2002	11816053
Chronic treatment with imipramine or mirtazapine antagonizes stress- and FG7142-induced increase in cortical norepinephrine output in freely moving rats.	2002 Jan	11746735
A double-blind, placebo-controlled study of antidepressant augmentation with mirtazapine.	2002 Jan 15	11822997
Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra.	2002 Jan-Feb	11812544
Heart rate variability as predictor of nonresponse to mirtazapine in panic disorder: a preliminary study.	2002 Mar	11892720
Antidepressant treatments induce the expression of basic fibroblast growth factor in cortical and hippocampal neurons.	2002 May	11961119

Patents

Sample Use Guides

In Vivo Use Guide

The initial dosage of Tolvon should be judged individually. It is recommended that treatment begins with a daily dose of 30mg given in three divided doses or a single bedtime dose and be adjusted weekly in the light of the clinical response. The effective daily dose for adult patients usually lies between 30mg and 90mg (average 60mg) in divided doses or as a single bedtime dose. A maximum daily dose of 120mg should not be exceeded.

Route of Administration: Oral

In Vitro Use Guide

Binding of mianserin to 5-HT2A receptor was measured using radioligand binding assay, using [125I]R91150 as a radioligand, and cloned human receptors. pKi for displacement of R91150 was 4.3 nM.

Name

Type

Language

MIANSERIN

Official Name

English

DIBENZO(C,F)PYRAZINO(1,2-A)AZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-

Common Name

English

(±)-MIANSERIN

Common Name

English

MIANSERIN [MI]

Common Name

English

mianserin [INN]

Common Name

English

1,2,3,4,10,14B-HEXAHYDRO-2-METHYLDIBENZO(C,F)-PYRAZINO(1,2-A)AZEPINE

Common Name

English

Mianserin [WHO-DD]

Common Name

English

MIANSERIN [VANDF]

Common Name

English

J16.389I

Code

English

MIANSERIN [HSDB]

Common Name

English

TOLVON

Brand Name

English

MIANSERINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72900