U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N3.ClH
Molecular Weight 301.814
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESMIRTAZAPINE HYDROCHLORIDE

SMILES

Cl.CN1CCN2[C@H](C1)C3=CC=CC=C3CC4=CC=CN=C24

InChI

InChIKey=SISMRXGXKXMBKT-PKLMIRHRSA-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/t16-;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula C17H19N3
Molecular Weight 265.3529
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Esmirtazapine (S-(+)mirtazapine or ORG-50081) is an enantiomer of mirtazapine (REMERON®), a high-affinity antagonist at 5-HT2/5-HT3 and H1 receptors, used in the treatment of depression. Esmirtazapine has a shorter plasma half-life than the R(−) enantiomer. Esmirtazapine is preferentially metabolized into an 8-hydroxy glucuronide. Organon was developing esmirtazapine for the treatment of hot flushes (vasomotor symptoms) associated with the menopause and insomnia.

Approval Year

PubMed

PubMed

TitleDatePubMed
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.
2010-12-01
Cancer cachexia: traditional therapies and novel molecular mechanism-based approaches to treatment.
2010-12
QEEG Measures in Huntington's Disease: A Pilot Study.
2010-10-25
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.
2010-04-04
Local smoke-free policy development in Santa Fe, Argentina.
2010-04
Mania associated with mirtazepine treatment and mixed depression.
2010-01
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.
2010
Comorbidities of migraine.
2010
3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders.
2009-12-21
Algorithms for the assessment and management of insomnia in primary care.
2009-11-03
Undertreatment of menopausal symptoms and novel options for comprehensive management.
2009-11
Fibromyalgia and myofascial pain syndrome-a dilemma.
2009-10
Sexual side-effects of contemporary antidepressants: review.
2009-09
Brain potentials of conflict and error-likelihood following errorful and errorless learning in obsessive-compulsive disorder.
2009-08-12
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.
2009-08-07
Management of difficult urticaria.
2009-07
Treatment with selective serotonin reuptake inhibitors and mirtapazine results in differential brain activation by visual erotic stimuli in patients with major depressive disorder.
2009-06
Incidence of major malformations in infants following antidepressant exposure in pregnancy: results of a large prospective cohort study.
2009-04
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.
2009-01
Routing protocols in wireless sensor networks.
2009
A new paradigm for the prediction of antidepressant treatment response.
2009
Brain-derived neurotrophic factor: role in depression and suicide.
2009
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
Mirtazapine: a review of its use in major depression and other psychiatric disorders.
2009
Triple reuptake inhibitors: the next generation of antidepressants.
2008-12
Neuropharmacology.
2008-10
Triple reuptake inhibitors: a premise and promise.
2008-09
A postmenopausal woman presenting with Ekbom syndrome associated with recurrent depressive disorder: a case report.
2008-07-22
Pharmacological management of panic disorder.
2008-02
Outcomes after isolated mirtazapine (Remeron) supratherapeutic ingestions.
2008-01
Treatment of depression as part of end-of-life care.
2008
Toward achieving optimal response: understanding and managing antidepressant side effects.
2008
5-HT(2A) inverse-agonists for the treatment of insomnia.
2008
Post-traumatic stress disorder.
2007-08-01
"Add-On"-therapy with an individualized preparation consisting of free amino acids for patients with a major depression.
2007-06
Essential tremor.
2007-05-01
A survey of combination antidepressant use in Australia.
2007-02
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007-01
Family history, early adversity and the hypothalamic-pituitary-adrenal (HPA) axis: Mediation of the vulnerability to mood disorders.
2007
[Differentiated approach to the therapy of endogenous anxious depression].
2007
[Depressive disturbances during antiviral therapy in patients with type C hepatitis].
2007
Improvement in cognitive and psychosocial functioning and self image among adolescent inpatient suicide attempters.
2006-12-29
Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review.
2006-12
Prophylaxis of migraine.
2006-09
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].
2006
Repeated treatment with mirtazepine induces brain-derived neurotrophic factor gene expression in rats.
2005-12
Onset of improvement and response to mirtazapine in depression: a multicenter naturalistic study of 4771 patients.
2005-03
Behavioral disturbances in dementia.
2003-03
Pathophysiology of depression and mechanisms of treatment.
2002-03
Treating age-related changes in somatotrophic hormones, sleep, and cognition.
2001-09
Patents

Sample Use Guides

Phase III trials: 0.5-18 mg once daily for 1-52 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:12:07 GMT 2025
Edited
by admin
on Mon Mar 31 22:12:07 GMT 2025
Record UNII
J12BQ47O1N
Record Status Validated (UNII)
Record Version
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Name Type Language
ESMIRTAZAPINE HYDROCHLORIDE
Common Name English
(S)-(+)-MIRTAZAPINE MONOHYDROCHLORIDE
Preferred Name English
MIRTAZAPINE HYDROCHLORIDE, (S)-
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), (14BS)-
Systematic Name English
Code System Code Type Description
PUBCHEM
71576069
Created by admin on Mon Mar 31 22:12:07 GMT 2025 , Edited by admin on Mon Mar 31 22:12:07 GMT 2025
PRIMARY
CAS
1448014-35-4
Created by admin on Mon Mar 31 22:12:07 GMT 2025 , Edited by admin on Mon Mar 31 22:12:07 GMT 2025
PRIMARY
FDA UNII
J12BQ47O1N
Created by admin on Mon Mar 31 22:12:07 GMT 2025 , Edited by admin on Mon Mar 31 22:12:07 GMT 2025
PRIMARY
DRUG BANK
DBSALT002352
Created by admin on Mon Mar 31 22:12:07 GMT 2025 , Edited by admin on Mon Mar 31 22:12:07 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
RACEMATE -> ENANTIOMER