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
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
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 | ( + / - ) |
DescriptionSources: https://www.drugbank.ca/drugs/DB06148Curator'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
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 | Condition | Potency |
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Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
4.3 nM [Ki] | ||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
4.4 nM [Ki] | ||
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
1.7 nM [Ki] | ||
Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
4.8 nM [Ki] | ||
Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
3.8 nM [Ki] | ||
Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415 |
101.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | TOVLON Approved UseFor the treatment of major depression. |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Expression of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors in the mouse embryo. | 2000 Nov |
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Meta-analytical studies on new antidepressants. | 2001 |
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Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis. | 2001 |
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Possible neurobiological mechanisms underlying faster onset of antidepressant action. | 2001 |
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Laser ablation reveals regulation of ciliary activity by serotonergic neurons in molluscan embryos. | 2001 Apr |
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Mirtazapine and bone marrow suppression: a case report. | 2001 Aug |
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Mirtazapine for excessive masturbation in an adolescent with autism. | 2001 Aug |
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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 |
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Mirtazapine versus venlafaxine in hospitalized severely depressed patients with melancholic features. | 2001 Aug |
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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 |
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Altered dendritic spine density in animal models of depression and in response to antidepressant treatment. | 2001 Dec 1 |
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Pharmacological characterisation of the decrease in 5-HT synthesis in the mouse brain evoked by the selective serotonin re-uptake inhibitor citalopram. | 2001 Feb |
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Following long-term training with citalopram, both mirtazapine and mianserin block its discriminative stimulus properties in rats. | 2001 Jan |
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Serotonergic mechanism in imipramine induced antinociception in rat tail flick test. | 2001 Jan |
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Mirtazepine: heir apparent to amitriptyline? | 2001 Jan-Feb |
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[Postoperative pain syndrome and its relationship with individual psychological features of personality]. | 2001 Jul-Aug |
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An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice. | 2001 Jun |
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A placebo-controlled, crossover trial of granisetron in SRI-induced sexual dysfunction. | 2001 Jun |
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SSRI and mirtazapine in PTSD. | 2001 Mar |
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Discovery of a novel member of the histamine receptor family. | 2001 Mar |
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[Comparative studies of adverse effects in patients with refractory depression treated with amitryptyline, mianserin and unilateral ECT]. | 2001 Mar-Apr |
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Neuropharmacological analysis of the role of the serotoninergic system in forming hyperalgesia in neurotic rats. | 2001 May-Jun |
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Effect of antidepressants on ATP-dependent calcium uptake by neuronal endoplasmic reticulum. | 2001 Nov |
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The effect of mirtazapine in panic disorder: an open label pilot study with a single-blind placebo run-in period. | 2001 Nov |
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Mirtazapine versus fluoxetine in the treatment of panic disorder. | 2001 Oct |
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Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. | 2001 Oct |
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Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study. | 2002 |
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Mirtazapine overdose with benign outcome. | 2002 Apr |
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Mirtazapine may have the propensity for developing a restless legs syndrome? A case report. | 2002 Apr |
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PET evaluation of a tetracyclic, atypical antidepressant, [N-methyl-11C]mianserin, in the living porcine brain. | 2002 Apr |
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Serotonin syndrome and atypical antipsychotics. | 2002 Apr |
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Severe serotonin syndrome induced by mirtazapine monotherapy. | 2002 Apr |
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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 |
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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 |
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Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets. | 2002 Apr 15 |
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[Unexpected drug-interaction]. | 2002 Feb |
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Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects--a possible opioid involvement in severe depression? | 2002 Feb-Apr |
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Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra. | 2002 Jan-Feb |
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Successful treatment of recurrent brief depression with reboxetine -- a single case analysis. | 2002 Mar |
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Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors. | 2002 Mar |
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Heart rate variability as predictor of nonresponse to mirtazapine in panic disorder: a preliminary study. | 2002 Mar |
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Mianserin or placebo as adjuncts to typical antipsychotics in resistant schizophrenia. | 2002 Mar |
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Antidepressant treatments induce the expression of basic fibroblast growth factor in cortical and hippocampal neurons. | 2002 May |
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Modulation of cellular expression of glucocorticoid receptor and glucocorticoid response element-DNA binding in rat brain during alcohol drinking and withdrawal. | 2002 May |
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Stimulus generalization by fenfluramine in a quipazine-ketanserin drug discrimination is not dependent on indirect serotonin release. | 2002 May |
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Mirtazapine, yohimbine or olanzapine augmentation therapy for serotonin reuptake-associated female sexual dysfunction: a randomized, placebo controlled trial. | 2002 May-Jun |
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Molecular characterisation of antidepressant effects in the mouse brain using gene expression profiling. | 2002 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.medicines.org.au/files/mkptolvo.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15771415
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
Edited
Sat Jun 26 02:34:11 UTC 2021
by
admin
on
Sat Jun 26 02:34:11 UTC 2021
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Record UNII |
250PJI13LM
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C72900
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WHO-ATC |
N06AX03
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NCI_THESAURUS |
C265
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NCI_THESAURUS |
C66885
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WHO-VATC |
QN06AX03
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Code System | Code | Type | Description | ||
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CHEMBL6437
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PRIMARY | |||
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DB06148
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PRIMARY | |||
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2543
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PRIMARY | |||
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Mianserin
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4184
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6929
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246-088-6
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PRIMARY | |||
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1796
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PRIMARY | |||
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M7521
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PRIMARY | Merck Index | ||
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C87209
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D008803
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MIANSERIN
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135
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24219-97-4
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SUB08939MIG
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7182
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250PJI13LM
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24219-97-4
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Metabolizing reaction by CYP2D6: O-demethylation
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
Pharmacological action: Tricyclic antidepressant drug (TCA)
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TARGET -> AGONIST |
SHORT-ACTING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
The plasma concentration of the compound was within the predicted therapeutic range in only 43% of patients.
AMOUNT ADMINISTERED
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |