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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
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

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
Mirtazepine: heir apparent to amitriptyline?	2001 Jan-Feb	11406877
Pathophysiology of depression and mechanisms of treatment.	2002 Mar	22033824
Mirtazepine overdose and miosis.	2003	14705856
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.	2005	16156382
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].	2006	17211109
Improvement in cognitive and psychosocial functioning and self image among adolescent inpatient suicide attempters.	2006 Dec 29	17196100
Family history, early adversity and the hypothalamic-pituitary-adrenal (HPA) axis: Mediation of the vulnerability to mood disorders.	2007	19300594
[Depressive disturbances during antiviral therapy in patients with type C hepatitis].	2007	17882814
A survey of combination antidepressant use in Australia.	2007 Feb	17464630
Treatment of depression as part of end-of-life care.	2008	21720540
Toward achieving optimal response: understanding and managing antidepressant side effects.	2008	19170398
Pharmacological management of panic disorder.	2008 Feb	18728820
Neuropharmacology.	2008 Oct	21593965
Routing protocols in wireless sensor networks.	2009	22291515
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.	2009 Aug 7	19701261
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.	2010	22110917
Local smoke-free policy development in Santa Fe, Argentina.	2010 Apr	19955534
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:52 GMT 2023`
Record UNII	I2U18E6JKA
Record Status	`Validated (UNII)`
Record Version

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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