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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 of MIANSERIN

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
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

Unknown
109281
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2575
 4.3 nM [Ki]
Antagonist
2575
 4.4 nM [Ki]
Antagonist
2575
 1.7 nM [Ki]
Antagonist
2575
 4.8 nM [Ki]
Antagonist
2575
 3.8 nM [Ki]
Inhibitor
7728
 101.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
TOVLON

Approved Use

For the treatment of major depression.
Palliative
Phase IV
63
Unknown

Approved Use

Unknown
Palliative
Phase IV
63
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Expression of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors in the mouse embryo.
2000 Nov
Meta-analytical studies on new antidepressants.
2001
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.
2001
Possible neurobiological mechanisms underlying faster onset of antidepressant action.
2001
Laser ablation reveals regulation of ciliary activity by serotonergic neurons in molluscan embryos.
2001 Apr
Mirtazapine and bone marrow suppression: a case report.
2001 Aug
Mirtazapine for excessive masturbation in an adolescent with autism.
2001 Aug
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
Mirtazapine versus venlafaxine in hospitalized severely depressed patients with melancholic features.
2001 Aug
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
Altered dendritic spine density in animal models of depression and in response to antidepressant treatment.
2001 Dec 1
Pharmacological characterisation of the decrease in 5-HT synthesis in the mouse brain evoked by the selective serotonin re-uptake inhibitor citalopram.
2001 Feb
Following long-term training with citalopram, both mirtazapine and mianserin block its discriminative stimulus properties in rats.
2001 Jan
Serotonergic mechanism in imipramine induced antinociception in rat tail flick test.
2001 Jan
Mirtazepine: heir apparent to amitriptyline?
2001 Jan-Feb
[Postoperative pain syndrome and its relationship with individual psychological features of personality].
2001 Jul-Aug
An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice.
2001 Jun
A placebo-controlled, crossover trial of granisetron in SRI-induced sexual dysfunction.
2001 Jun
SSRI and mirtazapine in PTSD.
2001 Mar
Discovery of a novel member of the histamine receptor family.
2001 Mar
[Comparative studies of adverse effects in patients with refractory depression treated with amitryptyline, mianserin and unilateral ECT].
2001 Mar-Apr
Neuropharmacological analysis of the role of the serotoninergic system in forming hyperalgesia in neurotic rats.
2001 May-Jun
Effect of antidepressants on ATP-dependent calcium uptake by neuronal endoplasmic reticulum.
2001 Nov
The effect of mirtazapine in panic disorder: an open label pilot study with a single-blind placebo run-in period.
2001 Nov
Mirtazapine versus fluoxetine in the treatment of panic disorder.
2001 Oct
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.
2001 Oct
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.
2002
Mirtazapine overdose with benign outcome.
2002 Apr
Mirtazapine may have the propensity for developing a restless legs syndrome? A case report.
2002 Apr
PET evaluation of a tetracyclic, atypical antidepressant, [N-methyl-11C]mianserin, in the living porcine brain.
2002 Apr
Serotonin syndrome and atypical antipsychotics.
2002 Apr
Severe serotonin syndrome induced by mirtazapine monotherapy.
2002 Apr
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
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
Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets.
2002 Apr 15
[Unexpected drug-interaction].
2002 Feb
Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects--a possible opioid involvement in severe depression?
2002 Feb-Apr
Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra.
2002 Jan-Feb
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis.
2002 Mar
Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors.
2002 Mar
Heart rate variability as predictor of nonresponse to mirtazapine in panic disorder: a preliminary study.
2002 Mar
Mianserin or placebo as adjuncts to typical antipsychotics in resistant schizophrenia.
2002 Mar
Antidepressant treatments induce the expression of basic fibroblast growth factor in cortical and hippocampal neurons.
2002 May
Modulation of cellular expression of glucocorticoid receptor and glucocorticoid response element-DNA binding in rat brain during alcohol drinking and withdrawal.
2002 May
Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release.
2002 May
Mirtazapine, yohimbine or olanzapine augmentation therapy for serotonin reuptake-associated female sexual dysfunction: a randomized, placebo controlled trial.
2002 May-Jun
Molecular characterisation of antidepressant effects in the mouse brain using gene expression profiling.
2002 May-Jun
Patents

Patents

JP2007505097A
22
US3534041
2

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
  • Download
Name Type Language
MIANSERIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
WHO-ATC N06AX03
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
NCI_THESAURUS C265
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
WHO-VATC QN06AX03
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL6437
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
DRUG BANK
DB06148
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
INN
2543
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
LACTMED
Mianserin
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
PUBCHEM
4184
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
RXCUI
6929
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
246-088-6
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
DRUG CENTRAL
1796
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
MERCK INDEX
M7521
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C87209
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
MESH
D008803
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
WIKIPEDIA
MIANSERIN
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
IUPHAR
135
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
CAS
24219-97-4
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
EVMPD
SUB08939MIG
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
HSDB
7182
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
FDA UNII
250PJI13LM
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
EPA CompTox
24219-97-4
Created by admin on Sat Jun 26 02:34:11 UTC 2021 , Edited by admin on Sat Jun 26 02:34:11 UTC 2021
PRIMARY
Related Record Type Details
Structure of MIANSERIN, (R)-
ENANTIOMER -> RACEMATE
Structure of MIANSERIN, (S)-
ENANTIOMER -> RACEMATE
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Metabolizing reaction by CYP2D6: O-demethylation
Structure of MIANSERIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Pharmacological action: Tricyclic antidepressant drug (TCA)
ALPHA-2A ADRENERGIC RECEPTOR
TARGET -> AGONIST
SHORT-ACTING
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Structure of 8-HYDROXYMIANSERIN
METABOLITE -> PARENT
Structure of MIANSERIN 2-OXIDE
METABOLITE -> PARENT
Structure of DESMETHYLMIANSERIN
METABOLITE ACTIVE -> PARENT
The plasma concentration of the compound was within the predicted therapeutic range in only 43% of patients.
AMOUNT ADMINISTERED
PLASMA
Related Record Type Details
Structure of MIANSERIN
ACTIVE MOIETY
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