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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 of ESMIRTAZAPINE

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
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

PubMed

TitleDatePubMed
Treating age-related changes in somatotrophic hormones, sleep, and cognition.
2001 Sep
Pathophysiology of depression and mechanisms of treatment.
2002 Mar
Behavioral disturbances in dementia.
2003 Mar
Repeated treatment with mirtazepine induces brain-derived neurotrophic factor gene expression in rats.
2005 Dec
Onset of improvement and response to mirtazapine in depression: a multicenter naturalistic study of 4771 patients.
2005 Mar
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].
2006
Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review.
2006 Dec
Improvement in cognitive and psychosocial functioning and self image among adolescent inpatient suicide attempters.
2006 Dec 29
Prophylaxis of migraine.
2006 Sep
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
Post-traumatic stress disorder.
2007 Aug 1
A survey of combination antidepressant use in Australia.
2007 Feb
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
"Add-On"-therapy with an individualized preparation consisting of free amino acids for patients with a major depression.
2007 Jun
Essential tremor.
2007 May 1
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
Triple reuptake inhibitors: the next generation of antidepressants.
2008 Dec
Pharmacological management of panic disorder.
2008 Feb
Outcomes after isolated mirtazapine (Remeron) supratherapeutic ingestions.
2008 Jan
A postmenopausal woman presenting with Ekbom syndrome associated with recurrent depressive disorder: a case report.
2008 Jul 22
Neuropharmacology.
2008 Oct
Triple reuptake inhibitors: a premise and promise.
2008 Sep
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
Incidence of major malformations in infants following antidepressant exposure in pregnancy: results of a large prospective cohort study.
2009 Apr
Brain potentials of conflict and error-likelihood following errorful and errorless learning in obsessive-compulsive disorder.
2009 Aug 12
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.
2009 Aug 7
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.
2009 Jan
Management of difficult urticaria.
2009 Jul
Treatment with selective serotonin reuptake inhibitors and mirtapazine results in differential brain activation by visual erotic stimuli in patients with major depressive disorder.
2009 Jun
Undertreatment of menopausal symptoms and novel options for comprehensive management.
2009 Nov
Algorithms for the assessment and management of insomnia in primary care.
2009 Nov 3
Fibromyalgia and myofascial pain syndrome-a dilemma.
2009 Oct
Sexual side-effects of contemporary antidepressants: review.
2009 Sep
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.
2010
Comorbidities of migraine.
2010
Local smoke-free policy development in Santa Fe, Argentina.
2010 Apr
3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders.
2010 Apr-Jun
Cancer cachexia: traditional therapies and novel molecular mechanism-based approaches to treatment.
2010 Dec
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.
2010 Dec 1
Mania associated with mirtazepine treatment and mixed depression.
2010 Jan
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.
2010 Jul-Sep
QEEG Measures in Huntington's Disease: A Pilot Study.
2010 Oct 25
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 Tue Oct 22 05:59:45 UTC 2019
Edited
by admin
on Tue Oct 22 05:59:45 UTC 2019
Record UNII
4685R51V7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESMIRTAZAPINE
INN   WHO-DD  
INN  
Official 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
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
ESMIRTAZAPINE [WHO-DD]
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
(S)-ORG 3770
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
NCI_THESAURUS C29756
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1366933
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
CAS
61337-87-9
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
ECHA (EC/EINECS)
262-714-0
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
INN
8620
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
PUBCHEM
3085218
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
NCI_THESAURUS
C76963
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
WIKIPEDIA
ESMIRTAZAPINE
Created by admin on Tue Oct 22 05:59:45 UTC 2019 , Edited by admin on Tue Oct 22 05:59:45 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
Scientific Literature
Related Record Type Details
ACTIVE MOIETY