ESMIRTAZAPINE

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

[H][C@]12CN(C)CCN1C3=C(CC4=C2C=CC=C4)C=CC=N3

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
Mirtazepine: heir apparent to amitriptyline?	2001 Jan-Feb	11406877
Treating age-related changes in somatotrophic hormones, sleep, and cognition.	2001 Sep	22034239
Mirtazepine overdose and miosis.	2003	14705856
Hypertensive urgency with clonidine and mirtazepine.	2004 Sep-Oct	15345793
Antidepressants and seizures: emphasis on newer agents and clinical implications.	2005 Dec	16351676
Onset of improvement and response to mirtazapine in depression: a multicenter naturalistic study of 4771 patients.	2005 Mar	18568129
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
Post-traumatic stress disorder.	2007 Aug 1	19454111
5-HT(2A) inverse-agonists for the treatment of insomnia.	2008	18673166
Pharmacological management of panic disorder.	2008 Feb	18728820
Neuropharmacology.	2008 Oct	21593965
Triple reuptake inhibitors: a premise and promise.	2008 Sep	20046357
Routing protocols in wireless sensor networks.	2009	22291515
Mirtazapine: a review of its use in major depression and other psychiatric disorders.	2009	19453203
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
Algorithms for the assessment and management of insomnia in primary care.	2009 Nov 3	19936140
Local smoke-free policy development in Santa Fe, Argentina.	2010 Apr	19955534
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.	2010 Dec 1	21122113
Mania associated with mirtazepine treatment and mixed depression.	2010 Jan	20178094

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 `Sat Dec 16 17:07:07 UTC 2023` Edited by `admin` on `Sat Dec 16 17:07:07 UTC 2023`
Record UNII	4685R51V7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESMIRTAZAPINE

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

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

(S)-ORG 3770

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66885