Esmirtazapine
Identification
- Name
- Esmirtazapine
- Accession Number
- DB06678
- 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Esmirtazapine (DB06678)
- 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
- External IDs
- ORG-44-20
- ORG-4420
- ORG-50,081
- SCH 900265
Pharmacology
- Indication
Investigated for use/treatment in insomnia and sleep disorders.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Unlock Additional DataAbatacept 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. Acemetacin The risk or severity of hypertension can be increased when Esmirtazapine is combined with Acemetacin. Acenocoumarol The risk or severity of adverse effects can be increased when Esmirtazapine is combined with Acenocoumarol. Acetaminophen The metabolism of Esmirtazapine can be decreased when combined with Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Esmirtazapine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Esmirtazapine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Esmirtazapine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- 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
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][[email protected]]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. [PubMed:18673166]
- 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. [PubMed:19775194]
- External Links
- PubChem Compound
- 3085218
- PubChem Substance
- 310264876
- ChemSpider
- 2342166
- ChEMBL
- CHEMBL1366933
- ZINC
- ZINC000000968310
- Wikipedia
- Esmirtazapine
Clinical Trials
- Clinical Trials
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 1 3 Completed Treatment Menopause / Vasomotor Symptoms 1 3 Terminated Treatment Dyssomnias / Psychiatric Disorder NOS / Sleep disorders and disturbances / Sleep Disorders, Intrinsic / Sleep Initiation and Maintenance Disorders 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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. [PubMed:26047892]
- 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. [PubMed:26047892]
- 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. [PubMed:26047892]
Enzymes
- 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. [PubMed:21246188]
- Link [Link]
Drug created on March 19, 2008 10:48 / Updated on June 12, 2020 10:52
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