Structure via PubChem · Public domain (PubChem)
esmirtazapine
Sign in to saveAlso known as (S)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
Esmirtazapine (ORG-50,081) is a tetracyclic antidepressant drug that was under development by Organon for the treatment of insomnia and vasomotor symptoms (e.g., hot flashes) associated with menopause. Esmirtazapine is the (S)-(+)-enantiomer of mirtazapine and possesses similar overall pharmacology, including inverse agonist actions at H1 and 5-HT2 receptors and antagonist actions at α2-adrenergic receptors.
Chemical data
- Formula
- C17H19N3
- Molecular weight
- 265.35 g/mol
- 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
- CN1CCN2[C@H](C1)C3=CC=CC=C3CC4=C2N=CC=C4
- InChIKey
- RONZAEMNMFQXRA-MRXNPFEDSA-N
- XLogP
- 3.3
- Polar surface area
- 19.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- mirtazapine
- Mass
- 265.157897608
Show 4 more facts
- chemical formula
- C₂₁H₂₃N₃O₄
- Commons category
- Esmirtazapine
- isomeric SMILES
- CN1CCN2c3c(cccn3)Cc4ccccc4[C@H]2C1
- canonical SMILES
- CN1CCN2c3ncccc3Cc3ccccc3C2C1
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Esmirtazapine (ORG-50,081) is a tetracyclic antidepressant drug that was under development by Organon for the treatment of insomnia and vasomotor symptoms (e.g., hot flashes) associated with menopause. Esmirtazapine is the (S)-(+)-enantiomer of mirtazapine and possesses similar overall pharmacology, including inverse agonist actions at H1 and 5-HT2 receptors and antagonist actions at α2-adrenergic receptors.
Notably, esmirtazapine has a shorter half life of around 10 hours, compared to R-mirtazapine and racemic mixture, which has a half-life of 18–40 hours. Merck has run several studies on low dose (3–4.5 mg) esmirtazapine for the treatment of insomnia. It is attractive for treating insomnia since it is a potent H1-inhibitor and a 5-HT2A antagonist. Unlike low-dose mirtazapine, the half life (10 hours) is short enough that next-day sedation may be manageable, however, for people with CYP2D6 polymorphisms, which constitute a sizable fraction of the population, the half-life is expected to be quite a bit longer. Merck researchers claimed that the incidence of next-day sedation was not a problem in one of their studies, but this claim has been challenged (15% of patients complained of daytime sleepiness vs 3.5% in the placebo group).
Excerpted from Wikipedia’s “esmirtazapine” article, available under the CC BY-SA 4.0 licence.