Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H19N3.ClH |
Molecular Weight | 301.814 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1CCN2C(C1)C3=C(CC4=C2N=CC=C4)C=CC=C3
InChI
InChIKey=SISMRXGXKXMBKT-UHFFFAOYSA-N
InChI=1S/C17H19N3.ClH/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20;/h2-8,16H,9-12H2,1H3;1H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11607047Curator's Comment: Description was created based on several sources, including:
http://psychiatryonline.org/doi/10.1176/appi.books.9781585623860.as21#u2014-09-19T084532.264-0400d1e2463
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020415s023s024.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607047
Curator's Comment: Description was created based on several sources, including:
http://psychiatryonline.org/doi/10.1176/appi.books.9781585623860.as21#u2014-09-19T084532.264-0400d1e2463
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020415s023s024.pdf
Mirtazapine, originally known as ORG 3770, was first synthesized by the Department of Medicinal Chemistry of NV Organon in the Netherlands (Kaspersen et al. 1989). First approved for use in major depression in the Netherlands in 1994, mirtazapine was introduced in the United States in 1996. The antidepressant mirtazapine has a dual mode of action. It is a noradrenergic and specific serotonergic antidepressant (NaSSA) that acts by antagonizing the adrenergic alpha2-autoreceptors and alpha2-heteroreceptors as well as by blocking 5-HT2 and 5-HT3 receptors. It enhances, therefore, the release of norepinephrine and 5-HT1A-mediated serotonergic transmission. This dual mode of action may conceivably be responsible for mirtazapine's rapid onset of action.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10333981
Curator's Comment: Mirtazapine entered the brain readily
https://www.ncbi.nlm.nih.gov/pubmed/14726991
Originator
Sources: http://psychiatryonline.org/doi/10.1176/appi.books.9781585623860.as21#u2014-09-19T084532.264-0400d1e2463
Curator's Comment: Kaspersen et al. 1989
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607047 |
7.0 null [pKi] | ||
Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607047 |
8.62 null [pKi] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607047 |
8.1 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | REMERON Approved UseREMERON (mirtazapine) Tablets are indicated for the treatment of major depressive disorder. The efficacy of REMERON in the treatment of major depressive disorder was established in 6-week controlled trials of outpatients whose diagnoses corresponded most closely to the Diagnostic and Statistical Manual of Mental Disorders – 3rd edition (DSM-III) category of major depressive disorder (see CLINICAL PHARMACOLOGY). A major depressive episode (DSM-IV) implies a prominent and relatively persistent (nearly every day for at least 2 weeks) depressed or dysphoric mood that usually interferes with daily functioning, and includes at least 5 of the following 9 symptoms: depressed mood, loss of interest in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt, or suicidal ideation. The effectiveness of REMERON in hospitalized depressed patients has not been adequately studied. The efficacy of REMERON in maintaining a response in patients with major depressive disorder for up to 40 weeks following 8 to 12 weeks of initial open-label treatment was demonstrated in a placebo-controlled trial. Nevertheless, the physician who elects to use REMERON for extended periods should periodically re-evaluate the long-term usefulness of the drug for the individual patient (see CLINICAL PHARMACOLOGY). Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32.3 μg/L |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
345 μg × h/L |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.2 h |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
30 h |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15% |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
15% |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRTAZAPINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
75 mg single, oral Highest studied dose |
healthy, 18-35 years |
|
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, 55 years n = 1 Health Status: unhealthy Age Group: 55 years Sex: F Population Size: 1 Sources: |
Disc. AE: Angle closure glaucoma... AEs leading to discontinuation/dose reduction: Angle closure glaucoma (1 patient) Sources: |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 453 Health Status: unhealthy Age Group: adult Population Size: 453 Sources: |
Disc. AE: Somnolence, Nausea... AEs leading to discontinuation/dose reduction: Somnolence (10.4%) Sources: Nausea (1.5%) |
15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Condition: major depressive disorde Age Group: children Sex: M+F Sources: |
Other AEs: Suicidal tendency, Suicidal behavior... Other AEs: Suicidal tendency Sources: Suicidal behavior |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Angle closure glaucoma | 1 patient Disc. AE |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, 55 years n = 1 Health Status: unhealthy Age Group: 55 years Sex: F Population Size: 1 Sources: |
Nausea | 1.5% Disc. AE |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 453 Health Status: unhealthy Age Group: adult Population Size: 453 Sources: |
Somnolence | 10.4% Disc. AE |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 453 Health Status: unhealthy Age Group: adult Population Size: 453 Sources: |
Suicidal behavior | 15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Condition: major depressive disorde Age Group: children Sex: M+F Sources: |
|
Suicidal tendency | 15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Condition: major depressive disorde Age Group: children Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak | ||||
weak | ||||
weak | no (co-administration study) Comment: mirtazapine caused no changes on the pharmacokinetics of paroxetine or amitriptyline Sources: https://pubmed.ncbi.nlm.nih.gov/31587356/ |
|||
yes | ||||
yes |
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Hypertensive urgency induced by an interaction of mirtazapine and clonidine. | 2000 Apr |
|
Third-generation antidepressants: do they offer advantages over the SSRIs? | 2001 |
|
Meta-analytical studies on new antidepressants. | 2001 |
|
Algorithm for the treatment of chronic depression. | 2001 |
|
Incidence of sexual dysfunction associated with antidepressant agents: a prospective multicenter study of 1022 outpatients. Spanish Working Group for the Study of Psychotropic-Related Sexual Dysfunction. | 2001 |
|
Mirtazapine and bone marrow suppression: a case report. | 2001 Aug |
|
Comment: serotonin syndrome induced by fluvoxamine and mirtazapine. | 2001 Dec |
|
An open trial of mirtazapine in menopausal women with depression unresponsive to estrogen replacement therapy. | 2001 Dec |
|
First report of mirtazapine-induced arthralgia. | 2001 Dec |
|
A naturalistic open-label study of mirtazapine in autistic and other pervasive developmental disorders. | 2001 Fall |
|
Screening for detection of new antidepressants, neuroleptics, hypnotics, and their metabolites in urine by GC-MS developed using rat liver microsomes. | 2001 Feb |
|
Following long-term training with citalopram, both mirtazapine and mianserin block its discriminative stimulus properties in rats. | 2001 Jan |
|
Mirtazepine: heir apparent to amitriptyline? | 2001 Jan-Feb |
|
A placebo-controlled, crossover trial of granisetron in SRI-induced sexual dysfunction. | 2001 Jun |
|
Efficacy and safety of mirtazapine in major depressive disorder patients after SSRI treatment failure: an open-label trial. | 2001 Jun |
|
Mitrazapine-associated palinopsia. | 2001 May |
|
Does mirtazapine have a more rapid onset than SSRIs? | 2001 May |
|
Possible serotonin syndrome in association with 5-HT(3) antagonist agents. | 2001 May-Jun |
|
Peripheral edema associated with mirtazapine. | 2001 Nov |
|
[Interference in the serotoninergic and noradrenergic system. Faster out of depression]. | 2001 Nov 1 |
|
Trait anxiety and the effect of a single high dose of diazepam in unipolar depression. | 2001 Nov-Dec |
|
Fluvoxamine augmentation increases serum mirtazapine concentrations three- to fourfold. | 2001 Oct |
|
Treatment of mood-congruent psychotic depression with imipramine. | 2001 Oct |
|
Mirtazapine may be useful in treating nausea and insomnia of cancer chemotherapy. | 2001 Sep |
|
Permutation-validated principal components analysis of microarray data. | 2002 |
|
Prevalence of sexual dysfunction among newer antidepressants. | 2002 Apr |
|
Serotonin syndrome and atypical antipsychotics. | 2002 Apr |
|
Severe serotonin syndrome induced by mirtazapine monotherapy. | 2002 Apr |
|
Spectrophotometric, spectrofluorimetric, HPLC and CZE determination of mirtazapine in pharmaceutical tablets. | 2002 Apr 15 |
|
Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol. | 2002 Aug |
|
Determination of mirtazapine and its demethyl metabolite in plasma by high-performance liquid chromatography with ultraviolet detection. Application to management of acute intoxication. | 2002 Aug 5 |
|
Intravenous mirtazapine in the treatment of depressed inpatients. | 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 |
|
Chronic treatment with imipramine or mirtazapine antagonizes stress- and FG7142-induced increase in cortical norepinephrine output in freely moving rats. | 2002 Jan |
|
A double-blind, placebo-controlled study of antidepressant augmentation with mirtazapine. | 2002 Jan 15 |
|
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 Jan 31 |
|
Body weight changes associated with psychopharmacology. | 2002 Jul |
|
Mirtazapine in the treatment of panic disorder. | 2002 Jul |
|
Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine. | 2002 Jul 18 |
|
Separation of new antidepressants and their metabolites by micellar electrokinetic capillary chromatography. | 2002 Jun 15 |
|
New antidepressants in the treatment of neuropathic pain. A review. | 2002 Mar |
|
[Tolerability and efficacy of combined antidepressant therapy]. | 2002 Mar-Apr |
|
Acute and chronic hypertensive headache and hypertensive encephalopathy. | 2002 May |
|
Urinary incontinence with mirtazapine. | 2002 May |
|
Dystonia induced by mirtazapine. | 2002 May |
|
An open-label, crossover trial of mirtazapine (15 and 30 mg) in cancer patients with pain and other distressing symptoms. | 2002 May |
|
Mirtazapine, yohimbine or olanzapine augmentation therapy for serotonin reuptake-associated female sexual dysfunction: a randomized, placebo controlled trial. | 2002 May-Jun |
Sample Use Guides
The recommended starting dose for REMERON® (mirtazapine) Tablets is 15 mg/day, administered in a single dose. In the controlled clinical trials establishing the efficacy of REMERON in the treatment of major depressive disorder, the effective dose range was generally 15 to 45 mg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12655328
0.1 uM mirtazapine affects glucocorticoid receptors expression (U937 cells)
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DBSALT002298
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42CIX4573G
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207516-99-2
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11695149
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100000174295
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ACTIVE MOIETY
SUBSTANCE RECORD