ESMIRTAZAPINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H19N3
Molecular Weight	265.3529
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RONZAEMNMFQXRA-MRXNPFEDSA-N

InChI=1S/C17H19N3/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/t16-/m1/s1

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18370465 | https://www.ncbi.nlm.nih.gov/pubmed/10885584 | https://www.rxlist.com/remeron-drug.htm | https://adisinsight.springer.com/drugs/800021392

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.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.	2010-12-01	21122113
Cancer cachexia: traditional therapies and novel molecular mechanism-based approaches to treatment.	2010-12	21128029
QEEG Measures in Huntington's Disease: A Pilot Study.	2010-10-25	21037796
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.	2010-04-04	21179358
Local smoke-free policy development in Santa Fe, Argentina.	2010-04	19955534
Mania associated with mirtazepine treatment and mixed depression.	2010-01	20178094
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.	2010	22110917
Comorbidities of migraine.	2010	21188255
3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders.	2009-12-21	21179345
Algorithms for the assessment and management of insomnia in primary care.	2009-11-03	19936140
Undertreatment of menopausal symptoms and novel options for comprehensive management.	2009-11	19775194
Fibromyalgia and myofascial pain syndrome-a dilemma.	2009-10	20640108
Sexual side-effects of contemporary antidepressants: review.	2009-09	19670052
Brain potentials of conflict and error-likelihood following errorful and errorless learning in obsessive-compulsive disorder.	2009-08-12	19672309
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.	2009-08-07	19701261
Management of difficult urticaria.	2009-07	20161863
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	20046380
Incidence of major malformations in infants following antidepressant exposure in pregnancy: results of a large prospective cohort study.	2009-04	19321030
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.	2009-01	19440288
Routing protocols in wireless sensor networks.	2009	22291515
A new paradigm for the prediction of antidepressant treatment response.	2009	20135901
Brain-derived neurotrophic factor: role in depression and suicide.	2009	19721723
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
Mirtazapine: a review of its use in major depression and other psychiatric disorders.	2009	19453203
Triple reuptake inhibitors: the next generation of antidepressants.	2008-12	19587855
Neuropharmacology.	2008-10	21593965
Triple reuptake inhibitors: a premise and promise.	2008-09	20046357
A postmenopausal woman presenting with Ekbom syndrome associated with recurrent depressive disorder: a case report.	2008-07-22	18647415
Pharmacological management of panic disorder.	2008-02	18728820
Outcomes after isolated mirtazapine (Remeron) supratherapeutic ingestions.	2008-01	17976774
Treatment of depression as part of end-of-life care.	2008	21720540
Toward achieving optimal response: understanding and managing antidepressant side effects.	2008	19170398
5-HT(2A) inverse-agonists for the treatment of insomnia.	2008	18673166
Post-traumatic stress disorder.	2007-08-01	19454111
"Add-On"-therapy with an individualized preparation consisting of free amino acids for patients with a major depression.	2007-06	17401733
Essential tremor.	2007-05-01	19454072
A survey of combination antidepressant use in Australia.	2007-02	17464630
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007-01	17003167
Family history, early adversity and the hypothalamic-pituitary-adrenal (HPA) axis: Mediation of the vulnerability to mood disorders.	2007	19300594
[Differentiated approach to the therapy of endogenous anxious depression].	2007	18225507
[Depressive disturbances during antiviral therapy in patients with type C hepatitis].	2007	17882814
Improvement in cognitive and psychosocial functioning and self image among adolescent inpatient suicide attempters.	2006-12-29	17196100
Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review.	2006-12	16930948
Prophylaxis of migraine.	2006-09	19412475
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].	2006	17211109
Repeated treatment with mirtazepine induces brain-derived neurotrophic factor gene expression in rats.	2005-12	16391422
Onset of improvement and response to mirtazapine in depression: a multicenter naturalistic study of 4771 patients.	2005-03	18568129
Behavioral disturbances in dementia.	2003-03	22034255
Pathophysiology of depression and mechanisms of treatment.	2002-03	22033824
Treating age-related changes in somatotrophic hormones, sleep, and cognition.	2001-09	22034239

Patents

Sample Use Guides

In Vivo Use Guide

Phase III trials: 0.5-18 mg once daily for 1-52 weeks

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:45:25 GMT 2025` Edited by `admin` on `Wed Apr 02 08:45:25 GMT 2025`
Record UNII	4685R51V7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESMIRTAZAPINE

Official Name

English

(S)-ORG 3770

Preferred Name

English

PYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-, (14BS)-

Systematic Name

English

Esmirtazapine [WHO-DD]

Common Name

English

ORG-44-20

Code

English

(+)-MIRTAZAPINE

Common Name

English

(S)-MIRTAZAPINE

Common Name

English

S-(+)-MIRTAZAPINE

Common Name

English

(S)-6-AZAMIANSERIN

Common Name

English

MIRTAZAPINE, (S)-

Common Name

English

(14BS)-1,2,3,4,10,14B-HEXAHYDRO-2-METHYLPYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE

Common Name

English

esmirtazapine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885