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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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
α2C-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.7 pKi - 2
pKi 7.7 (Ki 1.8x10-8 M) [2]
Description: Inhibition of [3H]rauwolscine binding.
α2A-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 7.7 pKi - 2
pKi 7.7 (Ki 2x10-8 M) [2]
Description: Inhibition of [3H]rauwolscine binding.
5-HT2C receptor Primary target of this compound Hs Antagonist Antagonist 7.4 pKi - 2
pKi 7.4 (Ki 3.9x10-8 M) [2]
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 7.1 pIC50 - 3
pIC50 7.1 (IC50 8.511x10-8 M) [3]
α2B-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 6.7 pIC50 - 3
pIC50 6.7 (IC50 2.239x10-7 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