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

Molecular Formula	C18H20N2
Molecular Weight	264.3648
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 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
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.	2000 Apr	10764922
Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states.	2000 Feb	10611634
Meta-analytical studies on new antidepressants.	2001	11719915
Evidence of early onset of antidepressant effect in randomized controlled trials.	2001	11229783
Laser ablation reveals regulation of ciliary activity by serotonergic neurons in molluscan embryos.	2001 Apr	11257609
Mirtazapine and bone marrow suppression: a case report.	2001 Aug	11555082
Long-term treatment with antidepressant drugs reduces the sensitivity of cortical cholinergic neurons to the activating actions of stress and the anxiogenic drug FG 7142.	2001 Aug	11489459
Comment: serotonin syndrome induced by fluvoxamine and mirtazapine.	2001 Dec	11793645
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 review of the pharmacological and clinical profile of mirtazapine.	2001 Fall	11607047
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
An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice.	2001 Jun	11485052
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
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
Antidepressant drug treatments induce glial cell line-derived neurotrophic factor (GDNF) synthesis and release in rat C6 glioblastoma cells.	2001 Oct	11595754
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001 Oct	11561066
PET evaluation of a tetracyclic, atypical antidepressant, [N-methyl-11C]mianserin, in the living porcine brain.	2002 Apr	11929701
Imipramine, mianserine and maprotiline block delayed rectifier potassium current in ventricular myocytes.	2002 Feb	11846627
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
Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra.	2002 Jan-Feb	11812544
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

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 `Fri Dec 15 15:16:58 GMT 2023` Edited by `admin` on `Fri Dec 15 15:16:58 GMT 2023`
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 [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