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
Molecular Formula | C17H19N3 |
Molecular Weight | 265.3529 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date8.3471041E11 |
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 |
---|---|---|
Mirtazapine treats resting tremor, essential tremor, and levodopa-induced dyskinesias. | 1999 Sep 22 |
|
New 2-substituted 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine having highly active and potent central alpha 2-antagonistic activity as potential antidepressants. | 2000 Jan 3 |
|
Algorithm for the treatment of chronic depression. | 2001 |
|
Possible neurobiological mechanisms underlying faster onset of antidepressant action. | 2001 |
|
Evidence of early onset of antidepressant effect in randomized controlled trials. | 2001 |
|
Mirtazapine for excessive masturbation in an adolescent with autism. | 2001 Aug |
|
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 Dec |
|
Comment: serotonin syndrome induced by fluvoxamine and mirtazapine. | 2001 Dec |
|
A naturalistic open-label study of mirtazapine in autistic and other pervasive developmental disorders. | 2001 Fall |
|
A review of the pharmacological and clinical profile of mirtazapine. | 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 |
|
Drug-drug interaction studies with mirtazapine and carbamazepine in healthy male subjects. | 2001 Jan-Jun |
|
Serotonin syndrome: early management with cyproheptadine. | 2001 Jul-Aug |
|
A placebo-controlled, crossover trial of granisetron in SRI-induced sexual dysfunction. | 2001 Jun |
|
SSRI and mirtazapine in PTSD. | 2001 Mar |
|
Efficacy of mirtazapine add on therapy to haloperidol in the treatment of the negative symptoms of schizophrenia: a double-blind randomized placebo-controlled study. | 2001 Mar |
|
Mitrazapine-associated palinopsia. | 2001 May |
|
Peripheral edema associated with mirtazapine. | 2001 Nov |
|
The effect of mirtazapine in panic disorder: an open label pilot study with a single-blind placebo run-in period. | 2001 Nov |
|
Prevalence of sexual dysfunction among newer antidepressants. | 2002 Apr |
|
Mirtazapine may have the propensity for developing a restless legs syndrome? A case report. | 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 |
|
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 |
|
A survey of prescribing practices in the treatment of depression. | 2002 Jan |
|
A double-blind, placebo-controlled study of antidepressant augmentation with mirtazapine. | 2002 Jan 15 |
|
Mirtazapine in the treatment of panic disorder. | 2002 Jul |
|
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 |
|
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis. | 2002 Mar |
|
Acute and chronic hypertensive headache and hypertensive encephalopathy. | 2002 May |
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)
Substance Class |
Chemical
Created
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Record UNII |
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Record Status |
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Record Version |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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