CHEBI:6950 - mirtazapine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name mirtazapine
ChEBI ID CHEBI:6950
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB0463388, ChemicalBook:CB7463387, eMolecules:591516, Selleckchem:mirtazapine-remeron-avanza
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Mirtazapine, sold under the brand name Remeron among others, is an atypical tetracyclic antidepressant, and as such is used primarily to treat depression. Its effects may take up to four weeks but can also manifest as early as one to two weeks. It is often used in cases of depression complicated by anxiety or insomnia. The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants. It is taken by mouth. Common side effects include sleepiness, dizziness, increased appetite and weight gain. Serious side effects may include mania, low white blood cell count, and increased suicide among children. Withdrawal symptoms may occur with stopping. It is not recommended together with a monoamine oxidase inhibitor, although evidence supporting the danger of this combination has been challenged. It is unclear if use during pregnancy is safe. How it works is not clear, but it may involve blocking certain adrenergic and serotonin receptors. Chemically, it is a tetracyclic antidepressant, and is closely related to mianserin. It also has strong antihistaminergic effects. Mirtazapine came into medical use in the United States in 1996. The patent expired in 2004, and generic versions are available. In 2022, it was the 105th most commonly prescribed medication in the United States, with more than 6 million prescriptions.
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Formula C17H19N3
Net Charge 0
Average Mass 265.35290
Monoisotopic Mass 265.15790
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
InChIKey RONZAEMNMFQXRA-UHFFFAOYSA-N
SMILES CN1CCN2C(C1)c1ccccc1Cc1cccnc21
Roles Classification
Biological Role(s): alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
Application(s): alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
oneirogen
Any substance that produces or enhances dream-like states of consciousness.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
(via tetracyclic antidepressant )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mirtazapine (CHEBI:6950) has role α-adrenergic antagonist (CHEBI:37890)
mirtazapine (CHEBI:6950) has role anxiolytic drug (CHEBI:35474)
mirtazapine (CHEBI:6950) has role H1-receptor antagonist (CHEBI:37955)
mirtazapine (CHEBI:6950) has role histamine antagonist (CHEBI:37956)
mirtazapine (CHEBI:6950) has role oneirogen (CHEBI:146270)
mirtazapine (CHEBI:6950) has role serotonergic antagonist (CHEBI:48279)
mirtazapine (CHEBI:6950) is a benzazepine (CHEBI:35676)
mirtazapine (CHEBI:6950) is a tetracyclic antidepressant (CHEBI:50940)
IUPAC Name
2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
INNs Sources
mirtazapina ChEBI
mirtazapine ChEBI
mirtazapinum ChEBI
Synonyms Sources
1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepine ChemIDplus
Mirtazapine KEGG COMPOUND
Manual Xrefs Databases
1816 DrugCentral
2980 VSDB
C07570 KEGG COMPOUND
D00563 KEGG DRUG
DB00370 DrugBank
DE2614406 Patent
LSM-1706 LINCS
Mirtazapine Wikipedia
US4062848 Patent
View more database links
Registry Numbers Types Sources
549345 Beilstein Registry Number Beilstein
61337-67-5 CAS Registry Number ChemIDplus
Citations
Yang Y, Guangrong Z, Xiaojing W, Gu W (2022)
Fine-tuning pharmacological properties of mirtazapine antidepressant drug: a theoretical study.
Journal of biomolecular structure & dynamics 40, 7274-7282 [PubMed:33685359]
[show Abstract]
Almishri W, Davis RP, Shaheen AA, Altonsy MO, Jenne CN, Swain MG (2021)
The Antidepressant Mirtazapine Rapidly Shifts Hepatic B Cell Populations and Functional Cytokine Signatures in the Mouse.
Frontiers in immunology 12, 622537 [PubMed:33841403]
[show Abstract]
Kintz P, Raul JS, Ameline A (2021)
Evidence of repeated mirtazapine poisoning in children by hair analysis.
Journal of forensic sciences 66, 1165-1170 [PubMed:33559900]
[show Abstract]
McGowan KE, March KL, Finch CK (2021)
The Hunger for Mirtazapine: A Discontinuation Syndrome.
Journal of pain & palliative care pharmacotherapy 35, 113-116 [PubMed:33856954]
[show Abstract]
Sasao A, Yonemitsu K, Ohtsu Y, Tsutsumi H, Furukawa S, Kimura-Mishima S, Nishitani Y (2021)
High blood mirtazapine concentration in a newborn - A case of suspected postpartum infanticide.
Legal medicine (Tokyo, Japan) 48, 101830 [PubMed:33422759]
[show Abstract]
Rissardo JP, Caprara ALF (2020)
Mirtazapine-associated movement disorders: A literature review.
Tzu chi medical journal 32, 318-330 [PubMed:33163376]
[show Abstract]
Marshall NS, Yee BJ, Desai AV, Buchanan PR, Wong KK, Crompton R, Melehan KL, Zack N, Rao SG, Gendreau RM, Kranzler J, Grunstein RR (2008)
Two randomized placebo-controlled trials to evaluate the efficacy and tolerability of mirtazapine for the treatment of obstructive sleep apnea.
Sleep 31, 824-831 [PubMed:18548827]
[show Abstract]
Djulus J, Koren G, Einarson TR, Wilton L, Shakir S, Diav-Citrin O, Kennedy D, Voyer Lavigne S, De Santis M, Einarson A (2006)
Exposure to mirtazapine during pregnancy: a prospective, comparative study of birth outcomes.
The Journal of clinical psychiatry 67, 1280-1284 [PubMed:16965209]
[show Abstract]
Laakmann G, Schüle C, Baghai T, Waldvogel E, Bidlingmaier M, Strasburger C (2000)
Mirtazapine: an inhibitor of cortisol secretion that does not influence growth hormone and prolactin secretion.
Journal of clinical psychopharmacology 20, 101-103 [PubMed:10653218]
Gorman JM (1999)
Mirtazapine: clinical overview.
The Journal of clinical psychiatry 60 Suppl 17, 9-13; discussion 46-8 [PubMed:10446735]
[show Abstract]
Last Modified
08 July 2021