mirtazapine   Click here for help

GtoPdb Ligand ID: 7241

Synonyms: ORG-3770 | Remeron®
Approved drug
mirtazapine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Mirtazapine is a tetracyclic antidepressant with complex polypharmacology involving certain adrenergic and serotonin receptors [1]. It also has strong antihistamine effects.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: mirtazapine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 19.37
Molecular weight 265.16
XLogP 3.02
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCN2C(C1)c1ccccc1Cc1c2nccc1
Isomeric SMILES CN1CCN2C(C1)c1ccccc1Cc1c2nccc1
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
InChI Key RONZAEMNMFQXRA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
Mirtazapine has affinity for several GPCRs, but has highest measurable affinity for the α2-adrenoceptors (IC50 order of potency: 2A>2C>2B [3]) and the serotonin 5-HT2A and 5-HT2C receptors (Ki order of potency 2C>2A>7>1A [2,4]).
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2C receptor Primary target of this compound Hs Antagonist Antagonist 7.4 pKi - 2
⤷ pKi 7.4 (Ki 3.9x10-8 M) [2]
α2C-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.0 – 7.7 pKi - 2,6
⤷ pKi 7.0 – 7.7 [2,6]
Description: Inhibition of [3H]rauwolscine binding.
5-HT2A receptor Primary target of this compound Hs Antagonist Antagonist 7.2 pKi - 2
⤷ pKi 7.2 (Ki 6.9x10-8 M) [2]
α2A-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 6.8 – 7.1 pKi - 2,6
⤷ pKi 6.8 – 7.1 [2,6]
Description: Inhibition of [3H]rauwolscine binding.
α2B-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 6.1 – 6.7 pKi - 3,6
⤷ pKi 6.1 – 6.7 [3,6]
α2A-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.1 pIC50 - 3
⤷ pIC50 7.1 (IC50 8.511x10-8 M) [3]
α2C-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 6.7 pIC50 - 3
⤷ pIC50 6.7 (IC50 1.995x10-7 M) [3]
Ligand mentioned in the following text fields
Adrenoceptors overview