Esmirtazapine
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Identification
- Generic Name
- Esmirtazapine
- DrugBank Accession Number
- DB06678
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 265.36
Monoisotopic: 265.157897624 - Chemical Formula
- C17H19N3
- Synonyms
- (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
- Esmirtazapine
- External IDs
- ORG-44-20
- ORG-4420
- ORG-50,081
- SCH 900265
Pharmacology
- Indication
Investigated for use/treatment in insomnia and sleep disorders.
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHistamine H1 receptor inverse agonistHumans U5-hydroxytryptamine receptor 2 inverse agonistHumans UAlpha-2 adrenergic receptors antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
10 hours
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Esmirtazapine is combined with 1,2-Benzodiazepine. Abatacept The metabolism of Esmirtazapine can be increased when combined with Abatacept. Abiraterone The metabolism of Esmirtazapine can be decreased when combined with Abiraterone. Acebutolol The metabolism of Esmirtazapine can be decreased when combined with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Esmirtazapine is combined with Aceclofenac. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Esmirtazapine hydrochloride J12BQ47O1N 1448014-35-4 SISMRXGXKXMBKT-PKLMIRHRSA-N Esmirtazapine maleate I2U18E6JKA 680993-85-5 RPUBHMMISKEXSR-MLCLTIQSSA-N
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic alpha-2 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Anti-Anxiety Agents
- Antidepressive Agents
- Antidepressive Agents, Tetracyclic
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Dibenzazepines
- Heterocyclic Compounds, Fused-Ring
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Neurotransmitter Agents
- Psychotropic Drugs
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT3 Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as piperazinoazepines. These are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperazinoazepines
- Sub Class
- Not Available
- Direct Parent
- Piperazinoazepines
- Alternative Parents
- Benzazepines / Dialkylarylamines / N-methylpiperazines / Azepines / Aralkylamines / Pyridines and derivatives / Imidolactams / Benzenoids / Heteroaromatic compounds / Trialkylamines show 3 more
- Substituents
- 1,4-diazinane / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzazepine / Benzenoid / Dialkylarylamine / Heteroaromatic compound show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 4685R51V7M
- CAS number
- 61337-87-9
- InChI Key
- RONZAEMNMFQXRA-MRXNPFEDSA-N
- InChI
- 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
- IUPAC Name
- (7S)-5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene
- SMILES
- [H][C@]12CN(C)CCN1C1=C(CC3=CC=CC=C23)C=CC=N1
References
- General References
- Teegarden BR, Al Shamma H, Xiong Y: 5-HT(2A) inverse-agonists for the treatment of insomnia. Curr Top Med Chem. 2008;8(11):969-76. [Article]
- Lewis V: Undertreatment of menopausal symptoms and novel options for comprehensive management. Curr Med Res Opin. 2009 Nov;25(11):2689-98. doi: 10.1185/03007990903240519. [Article]
- External Links
- PubChem Compound
- 3085218
- PubChem Substance
- 310264876
- ChemSpider
- 2342166
- ChEMBL
- CHEMBL1366933
- ZINC
- ZINC000000968310
- Wikipedia
- Esmirtazapine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Dyssomnias / Insomnia / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Initiation and Maintenance Disorders 1 3 Completed Treatment Dyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorder; Elderly 1 3 Completed Treatment Dyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorders 1 3 Completed Treatment Insomnia 3 3 Completed Treatment Menopause / Postmenopausal Syndrome / Vasomotor Symptoms Associated With Menopause 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 114 to 116 Not Available water solubility Soluble in methanol and chloroform mg/mL (20 °C) Not Available - Predicted Properties
Property Value Source Water Solubility 1.1 mg/mL ALOGPS logP 2.9 ALOGPS logP 3.21 Chemaxon logS -2.4 ALOGPS pKa (Strongest Basic) 6.67 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 19.37 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 82.66 m3·mol-1 Chemaxon Polarizability 30.4 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-d9130d64adb6310701ef Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-913f8dc5f10907fef80b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-ddf46a43b9349fff4853 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0290000000-ae221826622a8b4e10ab Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05ts-0390000000-57dcefce42b9772033aa Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-2890000000-1abfa3040fba16eff924 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 161.34653 predictedDeepCCS 1.0 (2019) [M+H]+ 163.70451 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.79767 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsHistamine H1 receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inverse agonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inverse agonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Components:
Name | UniProt ID |
---|---|
5-hydroxytryptamine receptor 2A | P28223 |
5-hydroxytryptamine receptor 2B | P41595 |
5-hydroxytryptamine receptor 2C | P28335 |
References
- Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Components:
Name | UniProt ID |
---|---|
Alpha-2A adrenergic receptor | P08913 |
Alpha-2B adrenergic receptor | P18089 |
Alpha-2C adrenergic receptor | P18825 |
References
- Ivgy-May N, Ruwe F, Krystal A, Roth T: Esmirtazapine in non-elderly adult patients with primary insomnia: efficacy and safety from a randomized, 6-week sleep laboratory trial. Sleep Med. 2015 Jul;16(7):838-44. doi: 10.1016/j.sleep.2015.04.001. Epub 2015 Apr 16. [Article]
Enzymes
1. DetailsCytochrome P450 2D6
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Ramaekers JG, Conen S, de Kam PJ, Braat S, Peeters P, Theunissen EL, Ivgy-May N: Residual effects of esmirtazapine on actual driving performance: overall findings and an exploratory analysis into the role of CYP2D6 phenotype. Psychopharmacology (Berl). 2011 May;215(2):321-32. doi: 10.1007/s00213-010-2149-4. Epub 2011 Jan 19. [Article]
- Link [Link]
Drug created at March 19, 2008 16:48 / Updated at February 02, 2024 22:52