MIANSERIN

Possibly Marketed Outside US

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=CC=CC=C3CC4=CC=CC=C24

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 237 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2849	4.3 nM [Ki]
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2849	4.4 nM [Ki]
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2849	1.7 nM [Ki]
Alpha-2a adrenergic receptor 70 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2849	4.8 nM [Ki]
Alpha-2c adrenergic receptor 44 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Antagonist 2849	3.8 nM [Ki]
Norepinephrine transporter 197 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415	Inhibitor 8504	101.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 240 Sources: http://www.medicines.org.au/files/mkptolvo.pdf	Primary	Approved 8583	TOVLON Approved Use For the treatment of major depression.
Schizophrenia 305 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

C_max

Value	Dose	Analyte	Population
14.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27190632/	30 mg single, rectal dose: 30 mg route of administration: Rectal experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27190632/ \| https://www.info.pmda.go.jp/go/interview/4/181615_1179033F1020_4_014_1F.pdf#page=17	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
102 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7075657/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
157.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6824562/	0.15 mg/kg single, intravenous dose: 0.15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
275 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6824562/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
541.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27190632/	30 mg single, rectal dose: 30 mg route of administration: Rectal experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
435.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27190632/ \| https://www.info.pmda.go.jp/go/interview/4/181615_1179033F1020_4_014_1F.pdf#page=17	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1356 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7075657/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
9.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6824562/	0.15 mg/kg single, intravenous dose: 0.15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6824562/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6824562/	single, oral	MIANSERIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
18.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27190632/ \| https://www.info.pmda.go.jp/go/interview/4/181615_1179033F1020_4_014_1F.pdf#page=17	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7075657/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	MIANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/181615_1179033F1020_4_014_1F.pdf#page=18			MIANSERIN plasma	Homo sapiens population: age: sex: FEMALE / MALE food status:

Doses

Dose	Population	Adverse events
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20203131/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20203131/	Disc. AE: Bradycardia, Hypotension... AEs leading to discontinuation/dose reduction: Bradycardia Hypotension Giddiness Sources: https://pubmed.ncbi.nlm.nih.gov/20203131/
580 mg single, oral Overdose Dose: 580 mg Route: oral Route: single Dose: 580 mg Sources: https://pubmed.ncbi.nlm.nih.gov/589080/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/589080/	Disc. AE: Drowsiness, Dry mouth... AEs leading to discontinuation/dose reduction: Drowsiness Dry mouth Heart block Sources: https://pubmed.ncbi.nlm.nih.gov/589080/
900 mg single, oral Overdose Dose: 900 mg Route: oral Route: single Dose: 900 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3679249/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3679249/	Disc. AE: Complete heart block... AEs leading to discontinuation/dose reduction: Complete heart block Sources: https://pubmed.ncbi.nlm.nih.gov/3679249/
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1806624/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1806624/	Disc. AE: Tachycardia, Agitation... AEs leading to discontinuation/dose reduction: Tachycardia (1.9%) Agitation (1.3%) Nausea (1.3%) Vomiting (1.3%) Motor activity retarded (0.63%) Drowsiness (0.63%) Motor activity exaggerated (0.63%) Tremor (1.3%) Sleeplessness (1.3%) Headache (1.3%) Constipation (1.3%) Depressed mood (0.63%) Blurred vision (0.63%) Perspiration excessive (0.63%) Fainting (0.63%) Dizziness (0.63%) Weight gain (0.63%) Sources: https://pubmed.ncbi.nlm.nih.gov/1806624/

AEs

PubMed

Title	Date	PubMed
Antidepressant treatments induce the expression of basic fibroblast growth factor in cortical and hippocampal neurons.	2002-05	11961119
Modulation of cellular expression of glucocorticoid receptor and glucocorticoid response element-DNA binding in rat brain during alcohol drinking and withdrawal.	2002-05	11961084
Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release.	2002-05	11900772
Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets.	2002-04-15	11929680
Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects--a possible opioid involvement in severe depression?	2002-04-05	11931344
Mirtazapine overdose with benign outcome.	2002-04	11973120
Mirtazapine may have the propensity for developing a restless legs syndrome? A case report.	2002-04	11952928
PET evaluation of a tetracyclic, atypical antidepressant, [N-methyl-11C]mianserin, in the living porcine brain.	2002-04	11929701
Serotonin syndrome and atypical antipsychotics.	2002-04	11925312
Severe serotonin syndrome induced by mirtazapine monotherapy.	2002-04	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.	2002-04	11888558
In the rat forced swimming test, NA-system mediated interactions may prevent the 5-HT properties of some subacute antidepressant treatments being expressed.	2002-04	11872334
Mirtazapine, yohimbine or olanzapine augmentation therapy for serotonin reuptake-associated female sexual dysfunction: a randomized, placebo controlled trial.	2002-03-12	11886692
Molecular characterisation of antidepressant effects in the mouse brain using gene expression profiling.	2002-03-12	11886689
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis.	2002-03	11951149
Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors.	2002-03	11939713
Heart rate variability as predictor of nonresponse to mirtazapine in panic disorder: a preliminary study.	2002-03	11892720
Mianserin or placebo as adjuncts to typical antipsychotics in resistant schizophrenia.	2002-03	11890187
[Unexpected drug-interaction].	2002-02	11925849
Imipramine, mianserine and maprotiline block delayed rectifier potassium current in ventricular myocytes.	2002-02	11846627
Intravenous mirtazapine in the treatment of depressed inpatients.	2002-02	11788241
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.	2002-01-31	11850045
Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra.	2002-01-29	11812544
A double-blind, placebo-controlled study of antidepressant augmentation with mirtazapine.	2002-01-15	11822997
Chronic treatment with imipramine or mirtazapine antagonizes stress- and FG7142-induced increase in cortical norepinephrine output in freely moving rats.	2002-01	11746735
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.	2002	11927153
Mania associated with mirtazapine augmentation of fluoxetine.	2002	11816053
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.	2001-12-21	11742252
Altered dendritic spine density in animal models of depression and in response to antidepressant treatment.	2001-12-01	11746712
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.	2001-12	11856898
Meta-analysis of placebo-controlled trials with mirtazapine using the core items of the Hamilton Depression Scale as evidence of a pure antidepressive effect in the short-term treatment of major depression.	2001-12	11806859
Comment: serotonin syndrome induced by fluvoxamine and mirtazapine.	2001-12	11793645
An open trial of mirtazapine in menopausal women with depression unresponsive to estrogen replacement therapy.	2001-12	11788110
First report of mirtazapine-induced arthralgia.	2001-12	11777743
Relative safety of mirtazapine overdose.	2001-12	11757992
[Interference in the serotoninergic and noradrenergic system. Faster out of depression].	2001-11-01	11732403
Effect of antidepressants on ATP-dependent calcium uptake by neuronal endoplasmic reticulum.	2001-11	11760097
Peripheral edema associated with mirtazapine.	2001-11	11724109
The effect of mirtazapine in panic disorder: an open label pilot study with a single-blind placebo run-in period.	2001-11	11712626
Trait anxiety and the effect of a single high dose of diazepam in unipolar depression.	2001-10-31	11684140
[Toxicological analysis in the dawn of the third millenium].	2001-10-17	11602391
Efficacy of mirtazapine for prevention of depressive relapse: a placebo-controlled double-blind trial of recently remitted high-risk patients.	2001-10	11816867
Fluvoxamine augmentation increases serum mirtazapine concentrations three- to fourfold.	2001-10	11675851
Serotonin syndrome induced by fluvoxamine and mirtazapine.	2001-10	11675850
Prevention of the stress-induced increase in frontal cortical dopamine efflux of freely moving rats by long-term treatment with antidepressant drugs.	2001-10	11597820
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
A naturalistic open-label study of mirtazapine in autistic and other pervasive developmental disorders.	2001	11642476
A review of the pharmacological and clinical profile of mirtazapine.	2001	11607047
Availability of learned helplessness test as a model of depression compared to a forced swimming test in rats.	2001	11598420

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 `Mon Mar 31 17:52:48 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:48 GMT 2025`
Record UNII	250PJI13LM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIANSERIN

Official Name

English

TOLVON

Preferred 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

MIANSERINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72900