Esmirtazapine
PubChem CID
3085218
Structure
Molecular Formula
Synonyms
- Esmirtazapine
- (S)-Mirtazapine
- 61337-87-9
- (+)-Mirtazapine
- Esmirtazapine [INN]
Molecular Weight
265.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-08-09
- Modify:2025-01-11
Description
Esmirtazapine, known by the standardized identifier SCH 900265, was under development by Organon to treat insomnia and vasomotor symptoms associated with menopause. Esmirtazapine is the (S)-(+)-enantiomer of mirtazapine and possesses similar overall pharmacology. This includes inverse agonist activity of H1 and 5-HT2 receptors and antagonism of α2-adrenergic receptors. Merck has terminated its internal clinical development program for esmirtazapine as of March 2010.
ESMIRTAZAPINE is a small molecule drug with a maximum clinical trial phase of III (across all indications) and has 2 investigational indications.
A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.
Chemical Structure Depiction
(7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
RONZAEMNMFQXRA-MRXNPFEDSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CN1CCN2[C@H](C1)C3=CC=CC=C3CC4=C2N=CC=C4
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C17H19N3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
61364-37-2
- (N-methyl-11C)mirtazapine
- (S)-Mirtazapine
- 6 Azamianserin
- 6-azamianserin
- esmirtazapine
- mirtazapine
- Norset
- ORG 3770
- Org 50081
- ORG-3770
- ORG3770
- Remergil
- Remeron
- Rexer
- Zispin
- Esmirtazapine
- (S)-Mirtazapine
- 61337-87-9
- (+)-Mirtazapine
- Esmirtazapine [INN]
- S-Mirtazapine
- Mirtazapine, (s)-
- (s)-6-azamianserin
- (s)-org 3770
- Org-44-20
- (S)-1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
- Org 44-20
- UNII-4685R51V7M
- EINECS 262-714-0
- 4685R51V7M
- S-(+)-MIRTAZAPINE
- ESMIRTAZAPINE [WHO-DD]
- (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
- (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
- (14BS)-1,2,3,4,10,14B-HEXAHYDRO-2-METHYLPYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE
- PYRAZINO(2,1-A)PYRIDO(2,3-C)(2)BENZAZEPINE, 1,2,3,4,10,14B-HEXAHYDRO-2-METHYL-, (14BS)-
- esmirtazapina
- esmirtazapinum
- (R)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
- (7S)-5-methyl-2,5,19-triazatetracyclo(13.4.0.02,?.0?,13)nonadeca-1(15),8,10,12,16,18-hexaene
- (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,?.0?,13]nonadeca-1(15),8,10,12,16,18-hexaene
- (N-methyl-11C)mirtazapine
- (S)-Mirtazapine-13C-d3
- BIDD:PXR0200
- SCHEMBL49330
- CHEMBL1366933
- HY-B0352A
- RONZAEMNMFQXRA-MRXNPFEDSA-N
- DTXSID001029320
- GLXC-15311
- PDSP1_001530
- PDSP2_001514
- AKOS040736264
- DB06678
- DA-48862
- MS-23753
- CS-0086936
- NS00087199
- G17036
- Q3058085
- (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.0?,?.0?,??]nonadeca-1(15),8,10,12,16,18-hexaene
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
265.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
265.157897619 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
265.157897619 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
19.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
345
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
114 to 116
Soluble in methanol and chloroform mg/mL (20 °C)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
PubMed Count
Investigated for use/treatment in insomnia and sleep disorders.
Adrenergic alpha-2 Receptor Antagonists
Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)
Histamine H1 Antagonists
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)
Serotonin 5-HT3 Receptor Antagonists
Drugs that bind to but do not activate SEROTONIN 5-HT3 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT3 RECEPTOR AGONISTS. (See all compounds classified as Serotonin 5-HT3 Receptor Antagonists.)
Antidepressive Agents
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)
Anti-Anxiety Agents
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)
Serotonin 5-HT2 Receptor Antagonists
Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes. (See all compounds classified as Serotonin 5-HT2 Receptor Antagonists.)
10 hours
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=RONZAEMNMFQXRA-MRXNPFEDSA-N
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusEsmirtazapine [INN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0061337879ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useEsmirtazapinehttps://www.drugbank.ca/drugs/DB06678
- EPA DSSTox(S)-1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepinehttps://comptox.epa.gov/dashboard/DTXSID001029320CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-notice(S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepinehttps://echa.europa.eu/substance-information/-/substanceinfo/100.056.994(R)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepinehttps://echa.europa.eu/substance-information/-/substanceinfo/100.057.013
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsESMIRTAZAPINEhttps://www.dgidb.org/drugs/ncit:C76963
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licenceESMIRTAZAPINEhttps://platform.opentargets.org/drug/CHEMBL1366933
- EU Clinical Trials Register
- Japan Chemical Substance Dictionary (Nikkaji)
- Metabolomics Workbench
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Thieme ChemistryLICENSEThe Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc-nd/4.0/
- Wikidataesmirtazapinehttps://www.wikidata.org/wiki/Q3058085
- WikipediaEsmirtazapinehttps://en.wikipedia.org/wiki/Esmirtazapine
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlMirtazapinehttps://www.ncbi.nlm.nih.gov/mesh/2028243Adrenergic alpha-2 Receptor Antagonistshttps://www.ncbi.nlm.nih.gov/mesh/68058669Histamine H1 Antagonistshttps://www.ncbi.nlm.nih.gov/mesh/68006634Serotonin 5-HT3 Receptor Antagonistshttps://www.ncbi.nlm.nih.gov/mesh/68058831Antidepressive Agentshttps://www.ncbi.nlm.nih.gov/mesh/68000928Anti-Anxiety Agentshttps://www.ncbi.nlm.nih.gov/mesh/68014151Serotonin 5-HT2 Receptor Antagonistshttps://www.ncbi.nlm.nih.gov/mesh/68058830
- PubChem
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 390751309https://pubchem.ncbi.nlm.nih.gov/substance/390751309
- NCBI
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