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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 of ESMIRTAZAPINE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Behavioral disturbances in dementia.
2003 Mar
Compliance: the impact of adverse events and tolerability on the physician's treatment decisions.
2003 Sep
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
[Distribution effects of orthographic similarity and priming by masked repetition].
2005 Sep
[Compliance in psychiatry: results of a survey of depressed patients using orally disintegrating tablet].
2006
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
[Differentiated approach to the therapy of endogenous anxious depression].
2007
[Depressive disturbances during antiviral therapy in patients with type C hepatitis].
2007
Post-traumatic stress disorder.
2007 Aug 1
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
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
Triple reuptake inhibitors: the next generation of antidepressants.
2008 Dec
Pharmacological management of panic disorder.
2008 Feb
Outcomes after isolated mirtazapine (Remeron) supratherapeutic ingestions.
2008 Jan
A postmenopausal woman presenting with Ekbom syndrome associated with recurrent depressive disorder: a case report.
2008 Jul 22
Routing protocols in wireless sensor networks.
2009
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
Early presentation following overdose of modified-release paracetamol (Panadol Osteo) with biphasic and prolonged paracetamol absorption.
2009 Aug 7
Ethyl carbamate in alcoholic beverages from Mexico (tequila, mezcal, bacanora, sotol) and Guatemala (cuxa): market survey and risk assessment.
2009 Jan
Sexual side-effects of contemporary antidepressants: review.
2009 Sep
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.
2010
Local smoke-free policy development in Santa Fe, Argentina.
2010 Apr
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.
2010 Dec 1
Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Sat Dec 16 17:07:07 GMT 2023
Record UNII
4685R51V7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESMIRTAZAPINE
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
NCI_THESAURUS C29756
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1366933
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
CAS
61337-87-9
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
262-714-0
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
DRUG BANK
DB06678
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
INN
8620
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID001029320
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
PUBCHEM
3085218
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
FDA UNII
4685R51V7M
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
SMS_ID
100000174926
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
NCI_THESAURUS
C76963
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
WIKIPEDIA
ESMIRTAZAPINE
Created by admin on Sat Dec 16 17:07:08 GMT 2023 , Edited by admin on Sat Dec 16 17:07:08 GMT 2023
PRIMARY
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