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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.[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

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
Third-generation antidepressants: do they offer advantages over the SSRIs?
2001
Behavioral disturbances in dementia.
2003 Mar
Hypertensive urgency with clonidine and mirtazepine.
2004 Sep-Oct
Mirtazapine (Remeron) as treatment for non-mechanical vomiting after gastric bypass.
2005 May
Mirtazepine for MDMA-induced depression.
2005 May-Jun
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
Post-traumatic stress disorder.
2007 Aug 1
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Triple reuptake inhibitors: the next generation of antidepressants.
2008 Dec
Pharmacological management of panic disorder.
2008 Feb
Neuropharmacology.
2008 Oct
Triple reuptake inhibitors: a premise and promise.
2008 Sep
Brain-derived neurotrophic factor: role in depression and suicide.
2009
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
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
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
Undertreatment of menopausal symptoms and novel options for comprehensive management.
2009 Nov
Algorithms for the assessment and management of insomnia in primary care.
2009 Nov 3
Sexual side-effects of contemporary antidepressants: review.
2009 Sep
Extreme thermal sensitivity and pain-induced sensitization in a fibromyalgia patient.
2010
Comorbidities of migraine.
2010
Gene expression profiling in whole blood identifies distinct biological pathways associated with obesity.
2010 Dec 1
Behavioral and developmental changes in rats with prenatal exposure of mirtazapine.
2010 Jul-Sep
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 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
  • Download
Name Type Language
ESMIRTAZAPINE MALEATE
USAN   WHO-DD  
USAN  
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
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT001294
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
PUBCHEM
6451144
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL1366933
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
USAN
RR-49
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
CAS
680993-85-5
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
NCI_THESAURUS
C76940
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
SMS_ID
100000174954
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
FDA UNII
I2U18E6JKA
Created by admin on Fri Dec 15 15:45:52 GMT 2023 , Edited by admin on Fri Dec 15 15:45:52 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY