MIANSERIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H20N2.ClH
Molecular Weight	300.826
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YNPFMWCWRVTGKJ-UHFFFAOYSA-N

InChI=1S/C18H20N2.ClH/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;1H

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
RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist.	1999 Jul	10455251
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.	1999 May	10217294
Pharmacology of rapid-onset antidepressant treatment strategies.	2001	11444761
Mirtazapine versus venlafaxine in hospitalized severely depressed patients with melancholic features.	2001 Aug	11476127
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
Comment: serotonin syndrome induced by fluvoxamine and mirtazapine.	2001 Dec	11793645
First report of mirtazapine-induced arthralgia.	2001 Dec	11777743
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
Treatment of depression in the elderly.	2001 Feb 1	11272296
Serotonergic mechanism in imipramine induced antinociception in rat tail flick test.	2001 Jan	11211562
[Comparative study of paroxetine and mianserin in depression in elderly patients: efficacy, tolerance, serotonin dependence].	2001 Jan-Feb	11294041
[Postoperative pain syndrome and its relationship with individual psychological features of personality].	2001 Jul-Aug	11586624
Efficacy and safety of mirtazapine in major depressive disorder patients after SSRI treatment failure: an open-label trial.	2001 Jun	11465517
Transcranial magnetic stimulation and antidepressive drugs share similar cellular effects in rat hippocampus.	2001 Jun	11331140
Discovery of a novel member of the histamine receptor family.	2001 Mar	11179435
Mitrazapine-associated palinopsia.	2001 May	11411821
[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
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
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
Mania associated with mirtazapine augmentation of fluoxetine.	2002	11816053
Mirtazapine overdose with benign outcome.	2002 Apr	11973120
Imipramine, mianserine and maprotiline block delayed rectifier potassium current in ventricular myocytes.	2002 Feb	11846627
A double-blind, placebo-controlled study of antidepressant augmentation with mirtazapine.	2002 Jan 15	11822997
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 HYDROCHLORIDE

Official Name

English

MIANSERIN HYDROCHLORIDE [JAN]

Common Name

English

Mianserin hydrochloride [WHO-DD]

Common Name

English

ORG-GB 94

Code

English

MIANSERIN HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

NSC-759590

Code

English

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

Common Name

English

1,2,3,4,10,14b-Hexahydro-2-methyldibenzo[c,f]-pyrazino[1,2-a]azepine monohydrochloride

Common Name

English

TETRAMIDE

Brand Name

English

MIANSERIN HYDROCHLORIDE [MART.]

Common Name

English

MIANSERIN HYDROCHLORIDE [USAN]

Common Name

English

MIANSERIN HYDROCHLORIDE [MI]

Common Name

English

ORG GB 94

Code

English

MIANSERIN HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72900