ESMIRTAZAPINE MALEATE

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 Search

SMILES

OC(=O)\C=C/C(O)=O.[H][C@]12CN(C)CCN1C3=C(CC4=C2C=CC=C4)C=CC=N3

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

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
Pathophysiology of depression and mechanisms of treatment.	2002 Mar	22033824
Hypertensive urgency with clonidine and mirtazepine.	2004 Sep-Oct	15345793
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.	2005	16156382
Mirtazepine for MDMA-induced depression.	2005 May-Jun	16019980
Linezolid-associated serotonin syndrome after concomitant treatment with citalopram and mirtazepine in a critically ill bone marrow transplant recipient.	2005 Nov-Dec	16280409
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	16223499
[Distribution effects of orthographic similarity and priming by masked repetition].	2005 Sep	16248498
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].	2006	17211109
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
Post-traumatic stress disorder.	2007 Aug 1	19454111
A new paradigm for the prediction of antidepressant treatment response.	2009	20135901
Brain-derived neurotrophic factor: role in depression and suicide.	2009	19721723
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.	2009 Aug 7	19701261
Undertreatment of menopausal symptoms and novel options for comprehensive management.	2009 Nov	19775194
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.	2010	22110917
3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders.	2010 Apr-Jun	21179345
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.	2010 Jul-Sep	21179358

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

Name

Type

Language

ESMIRTAZAPINE MALEATE

Official Name

English

Esmirtazapine maleate [WHO-DD]

Common 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

ORG 50081

Code

English

MIRTAZAPINE MALEATE, (S)-

Common Name

English

ESMIRTAZAPINE MALEATE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29756