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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
Mirtazepine overdose and miosis.
2003
Behavioral disturbances in dementia.
2003 Mar
Hypertensive urgency with clonidine and mirtazepine.
2004 Sep-Oct
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.
2005
Repeated treatment with mirtazepine induces brain-derived neurotrophic factor gene expression in rats.
2005 Dec
Antidepressants and seizures: emphasis on newer agents and clinical implications.
2005 Dec
Evidence of cost-effective treatments for depression: a systematic review.
2005 Jan
Onset of improvement and response to mirtazapine in depression: a multicenter naturalistic study of 4771 patients.
2005 Mar
Mirtazapine (Remeron) as treatment for non-mechanical vomiting after gastric bypass.
2005 May
Mirtazepine for MDMA-induced depression.
2005 May-Jun
Linezolid-associated serotonin syndrome after concomitant treatment with citalopram and mirtazepine in a critically ill bone marrow transplant recipient.
2005 Nov-Dec
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
Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review.
2006 Dec
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
Toward achieving optimal response: understanding and managing antidepressant side effects.
2008
5-HT(2A) inverse-agonists for the treatment of insomnia.
2008
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
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
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.
2009 Jan
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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ACTIVE MOIETY