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

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
Third-generation antidepressants: do they offer advantages over the SSRIs?	2001	11735614
Treating age-related changes in somatotrophic hormones, sleep, and cognition.	2001 Sep	22034239
Pathophysiology of depression and mechanisms of treatment.	2002 Mar	22033824
Mirtazepine overdose and miosis.	2003	14705856
Acute zonisamide overdose: a death revisited.	2003 Jun	12776795
Behavioral disturbances in dementia.	2003 Mar	22034255
Compliance: the impact of adverse events and tolerability on the physician's treatment decisions.	2003 Sep	14550581
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
Repeated treatment with mirtazepine induces brain-derived neurotrophic factor gene expression in rats.	2005 Dec	16391422
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
Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review.	2006 Dec	16930948
Improvement in cognitive and psychosocial functioning and self image among adolescent inpatient suicide attempters.	2006 Dec 29	17196100
Prophylaxis of migraine.	2006 Sep	19412475
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
Post-traumatic stress disorder.	2007 Aug 1	19454111
Treatment of depression as part of end-of-life care.	2008	21720540
5-HT(2A) inverse-agonists for the treatment of insomnia.	2008	18673166
Triple reuptake inhibitors: the next generation of antidepressants.	2008 Dec	19587855
A postmenopausal woman presenting with Ekbom syndrome associated with recurrent depressive disorder: a case report.	2008 Jul 22	18647415
Neuropharmacology.	2008 Oct	21593965
Triple reuptake inhibitors: a premise and promise.	2008 Sep	20046357
Routing protocols in wireless sensor networks.	2009	22291515
A new paradigm for the prediction of antidepressant treatment response.	2009	20135901
Brain-derived neurotrophic factor: role in depression and suicide.	2009	19721723
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
Mirtazapine: a review of its use in major depression and other psychiatric disorders.	2009	19453203
Incidence of major malformations in infants following antidepressant exposure in pregnancy: results of a large prospective cohort study.	2009 Apr	19321030
Brain potentials of conflict and error-likelihood following errorful and errorless learning in obsessive-compulsive disorder.	2009 Aug 12	19672309
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.	2009 Aug 7	19701261
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.	2009 Jan	19440288
Management of difficult urticaria.	2009 Jul	20161863
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	20046380
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
Fibromyalgia and myofascial pain syndrome-a dilemma.	2009 Oct	20640108
Sexual side-effects of contemporary antidepressants: review.	2009 Sep	19670052
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.	2010	22110917
Comorbidities of migraine.	2010	21188255
Local smoke-free policy development in Santa Fe, Argentina.	2010 Apr	19955534
3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders.	2010 Apr-Jun	21179345
Cancer cachexia: traditional therapies and novel molecular mechanism-based approaches to treatment.	2010 Dec	21128029
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
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.	2010 Jul-Sep	21179358
QEEG Measures in Huntington's Disease: A Pilot Study.	2010 Oct 25	21037796

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

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