MIANSERIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H20N2
Molecular Weight	264.3655
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN2c3ccccc3Cc4ccccc4C2C1

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

Molecular Formula	C18H20N2
Molecular Weight	264.3655
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 211 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2575	4.3 nM [Ki]
Serotonin 2c (5-HT2c) receptor 101 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2575	4.4 nM [Ki]
Histamine H1 receptor 304 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2575	1.7 nM [Ki]
Alpha-2a adrenergic receptor 62 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2575	4.8 nM [Ki]
Alpha-2c adrenergic receptor 37 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2575	3.8 nM [Ki]
Norepinephrine transporter 175 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Inhibitor 7728	101.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 215 Sources: http://www.medicines.org.au/files/mkptolvo.pdf	Primary	Approved 8043	TOVLON Approved Use For the treatment of major depression.
Schizophrenia 276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12650957	Palliative	Phase IV 63	Unknown Approved Use Unknown
Opioid dependence 20 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
Availability of learned helplessness test as a model of depression compared to a forced swimming test in rats.	2001	11598420
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
First report of mirtazapine-induced arthralgia.	2001 Dec	11777743
Relative safety of mirtazapine overdose.	2001 Dec	11757992
Altered dendritic spine density in animal models of depression and in response to antidepressant treatment.	2001 Dec 1	11746712
Effects of voluntary ethanol intake on the expression of Ca(2+) /calmodulin-dependent protein kinase IV and on CREB expression and phosphorylation in the rat nucleus accumbens.	2001 Dec 21	11742252
A naturalistic open-label study of mirtazapine in autistic and other pervasive developmental disorders.	2001 Fall	11642476
A review of the pharmacological and clinical profile of mirtazapine.	2001 Fall	11607047
[Postoperative pain syndrome and its relationship with individual psychological features of personality].	2001 Jul-Aug	11586624
Effect of antidepressants on ATP-dependent calcium uptake by neuronal endoplasmic reticulum.	2001 Nov	11760097
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
[Interference in the serotoninergic and noradrenergic system. Faster out of depression].	2001 Nov 1	11732403
Trait anxiety and the effect of a single high dose of diazepam in unipolar depression.	2001 Nov-Dec	11684140
Efficacy of mirtazapine for prevention of depressive relapse: a placebo-controlled double-blind trial of recently remitted high-risk patients.	2001 Oct	11816867
Fluvoxamine augmentation increases serum mirtazapine concentrations three- to fourfold.	2001 Oct	11675851
Serotonin syndrome induced by fluvoxamine and mirtazapine.	2001 Oct	11675850
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
Mirtazapine versus fluoxetine in the treatment of panic disorder.	2001 Oct	11593305
Mirtazapine treatment of obsessive-compulsive disorder.	2001 Oct	11593084
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 may be useful in treating nausea and insomnia of cancer chemotherapy.	2001 Sep	11585276
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
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.	2002	11927153
Mirtazapine overdose with benign outcome.	2002 Apr	11973120
PET evaluation of a tetracyclic, atypical antidepressant, [N-methyl-11C]mianserin, in the living porcine brain.	2002 Apr	11929701
Serotonin syndrome and atypical antipsychotics.	2002 Apr	11925312
Severe serotonin syndrome induced by mirtazapine monotherapy.	2002 Apr	11918514
Induction of hyperlocomotion in mice exposed to a novel environment by inhibition of serotonin reuptake. A pharmacological characterization of diverse classes of antidepressant agents.	2002 Apr	11888558
In the rat forced swimming test, NA-system mediated interactions may prevent the 5-HT properties of some subacute antidepressant treatments being expressed.	2002 Apr	11872334
Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets.	2002 Apr 15	11929680
[Unexpected drug-interaction].	2002 Feb	11925849
Imipramine, mianserine and maprotiline block delayed rectifier potassium current in ventricular myocytes.	2002 Feb	11846627
Intravenous mirtazapine in the treatment of depressed inpatients.	2002 Feb	11788241
Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects--a possible opioid involvement in severe depression?	2002 Feb-Apr	11931344
Chronic treatment with imipramine or mirtazapine antagonizes stress- and FG7142-induced increase in cortical norepinephrine output in freely moving rats.	2002 Jan	11746735
Mirtazapine, but not fluvoxamine, normalizes the blunted REM sleep response to clonidine in depressed patients: implications for subsensitivity of alpha(2)-adrenergic receptors in depression.	2002 Jan 31	11850045
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis.	2002 Mar	11951149
Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors.	2002 Mar	11939713
Heart rate variability as predictor of nonresponse to mirtazapine in panic disorder: a preliminary study.	2002 Mar	11892720
Mianserin or placebo as adjuncts to typical antipsychotics in resistant schizophrenia.	2002 Mar	11890187
Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release.	2002 May	11900772
Mirtazapine, yohimbine or olanzapine augmentation therapy for serotonin reuptake-associated female sexual dysfunction: a randomized, placebo controlled trial.	2002 May-Jun	11886692
Molecular characterisation of antidepressant effects in the mouse brain using gene expression profiling.	2002 May-Jun	11886689

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.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 02:34:11 UTC 2021` Edited by `admin` on `Sat Jun 26 02:34:11 UTC 2021`
Record UNII	250PJI13LM
Record Status	`Validated (UNII)`
Record Version

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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 [VANDF]

Common Name

English

J16.389I

Code

English

MIANSERIN [HSDB]

Common Name

English

TOLVON

Brand Name

English

MIANSERINE

Common Name

English

MIANSERIN [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72900