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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N3.C4H4O4
Molecular Weight 381.425
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ESMIRTAZAPINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN1CCN2[C@H](C1)C3=CC=CC=C3CC4=CC=CN=C24

InChI

InChIKey=RPUBHMMISKEXSR-MLCLTIQSSA-N
InChI=1S/C17H19N3.C4H4O4/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20;5-3(6)1-2-4(7)8/h2-8,16H,9-12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Third-generation antidepressants: do they offer advantages over the SSRIs?
2001
Mirtazepine: heir apparent to amitriptyline?
2001 Jan-Feb
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
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.
2005
Mirtazapine (Remeron) as treatment for non-mechanical vomiting after gastric bypass.
2005 May
Mirtazepine for MDMA-induced depression.
2005 May-Jun
Chiral resolution and binding study of 1,3,4,14b-tetrahydro-2,10-dimethyl-2H,10H-pyrazino[2,1-d]pyrrolo[1,2-b] [1,2,5]benzotriazepine (10-methyl-10-azaaptazepine) and 2-methyl-1,3,4,14b-tetrahydro-2H-pyrazino[2,1-d]pyrrolo[1,2-b] [1,2,5]benzothiadiazepine 10,10-dioxide (tiaaptazepine).
2005 Nov-Dec
[Distribution effects of orthographic similarity and priming by masked repetition].
2005 Sep
Prophylaxis of migraine.
2006 Sep
Family history, early adversity and the hypothalamic-pituitary-adrenal (HPA) axis: Mediation of the vulnerability to mood disorders.
2007
Post-traumatic stress disorder.
2007 Aug 1
Essential tremor.
2007 May 1
Treatment of depression as part of end-of-life care.
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
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
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 01:37:43 UTC 2019
Edited
by admin
on Tue Oct 22 01:37:43 UTC 2019
Record UNII
I2U18E6JKA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESMIRTAZAPINE MALEATE
USAN   WHO-DD  
USAN  
Official Name English
(+)-(14BS)-2-METHYL-1,2,3,4,10,14B-HEXAHYDROPYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE (2Z)-BUTENEDIOATE
Common Name English
ORG-50081
Code English
PYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-, (14BS)-, (2Z)-2-BUTENEDIOATE (1:1)
Common Name English
ESMIRTAZAPINE MALEATE [WHO-DD]
Common Name English
ORG 50081
Code English
MIRTAZAPINE MALEATE, (S)-
Common Name English
ESMIRTAZAPINE MALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Tue Oct 22 01:37:43 UTC 2019 , Edited by admin on Tue Oct 22 01:37:43 UTC 2019
Code System Code Type Description
PUBCHEM
6451144
Created by admin on Tue Oct 22 01:37:43 UTC 2019 , Edited by admin on Tue Oct 22 01:37:43 UTC 2019
PRIMARY
ChEMBL
CHEMBL1366933
Created by admin on Tue Oct 22 01:37:43 UTC 2019 , Edited by admin on Tue Oct 22 01:37:43 UTC 2019
PRIMARY
CAS
680993-85-5
Created by admin on Tue Oct 22 01:37:43 UTC 2019 , Edited by admin on Tue Oct 22 01:37:43 UTC 2019
PRIMARY
NCI_THESAURUS
C76940
Created by admin on Tue Oct 22 01:37:43 UTC 2019 , Edited by admin on Tue Oct 22 01:37:43 UTC 2019
PRIMARY
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