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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
Structure of MIRTAZAPINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Mirtazapine entered the brain readily https://www.ncbi.nlm.nih.gov/pubmed/14726991

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.0 null [pKi]
8.62 null [pKi]
8.1 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
REMERON

Approved Use

REMERON (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 Date

8.3471041E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
75 mg single, oral
Highest studied dose
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
healthy, 18-35 years
Health Status: healthy
Age Group: 18-35 years
Sex: M
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, 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%)
Nausea (1.5%)
Sources:
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...
AEs

AEs

AESignificanceDosePopulation
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

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak
weak
weak
no (co-administration study)
Comment: mirtazapine caused no changes on the pharmacokinetics of paroxetine or amitriptyline
yes
yes
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
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
Patents

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
0.1 uM mirtazapine affects glucocorticoid receptors expression (U937 cells)
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:36:34 UTC 2023
Edited
by admin
on Sat Dec 16 08:36:34 UTC 2023
Record UNII
42CIX4573G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIRTAZAPINE HYDROCHLORIDE
Common Name English
PYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
DRUG BANK
DBSALT002298
Created by admin on Sat Dec 16 08:36:34 UTC 2023 , Edited by admin on Sat Dec 16 08:36:34 UTC 2023
PRIMARY
FDA UNII
42CIX4573G
Created by admin on Sat Dec 16 08:36:34 UTC 2023 , Edited by admin on Sat Dec 16 08:36:34 UTC 2023
PRIMARY
CAS
207516-99-2
Created by admin on Sat Dec 16 08:36:34 UTC 2023 , Edited by admin on Sat Dec 16 08:36:34 UTC 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
11695149
Created by admin on Sat Dec 16 08:36:34 UTC 2023 , Edited by admin on Sat Dec 16 08:36:34 UTC 2023
PRIMARY
SMS_ID
100000174295
Created by admin on Sat Dec 16 08:36:34 UTC 2023 , Edited by admin on Sat Dec 16 08:36:34 UTC 2023
PRIMARY
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