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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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.
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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 )
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View more via ChEBI Ontology
2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
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mirtazapina
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ChEBI
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mirtazapine
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ChEBI
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mirtazapinum
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ChEBI
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1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepine
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ChemIDplus
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Mirtazapine
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KEGG COMPOUND
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1816
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DrugCentral
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2980
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VSDB
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C07570
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KEGG COMPOUND
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D00563
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KEGG DRUG
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DB00370
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DrugBank
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DE2614406
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Patent
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LSM-1706
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LINCS
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Mirtazapine
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Wikipedia
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US4062848
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Patent
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549345
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Beilstein Registry Number
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Beilstein
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61337-67-5
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CAS Registry Number
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ChemIDplus
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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] It has become obvious that fluorinated drugs have a significant role in medicinal applications. In this study, the fluorination of mirtazapine antidepressant drug was investigated using density functional theory calculations. We found that the intramolecular hydrogen bonding and charge transfers of the mirtazapine drug were influenced by fluorine substitution. Our results also reveal that the fluorination altered the stability, solubility, and molecular polarity of the mirtazapine antidepressant drug. Moreover, our results show that the electronic spectra of fluorinated derivatives of the mirtazapine exhibit a red shift toward higher wavelengths compared to the original antidepressant drug. Our calculations show that the difference between G value of the gas and water (ΔG) of fluorinated derivatives of the mirtazapine drug was negative. We also found that the fluorination can increases the first hyperpolarizability of the mirtazapine antidepressant drug. Our results present an efficient strategy to improve the nonlinear optical responses of the antidepressant drugs. Consequently, the results of present study show that the fluorination of mirtazapine could be considered as a promising strategy to design antidepressant drugs with better pharmacological properties.Communicated by Ramaswamy H. Sarma. | 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]
IntroductionB cells are important regulators of both adaptive and innate immunity. The normal liver contains significant numbers of B cells, and their numbers increase dramatically in immune-mediated liver diseases. Our previous observations suggest a hepatoprotective effect of the antidepressant mirtazapine in human and experimental immune-mediated liver disease. Therefore, we performed a series of experiments to determine the impact of mirtazapine treatment on hepatic B cell homeostasis, as reflected by B cell number, trafficking and phenotype using flow cytometry (FCM) and intravital microscopy (IVM) analysis. Mirtazapine treatment rapidly induced a significant reduction in total hepatic B cell numbers, paralleled by a compositional shift in the predominant hepatic B cell subtype from B2 to B1. This shift in hepatic B cells induced by mirtazapine treatment was associated with a striking increase in total hepatic levels of the chemokine CXCL10, and increased production of CXCL10 by hepatic macrophages and dendritic cells. Furthermore, mirtazapine treatment led to an upregulation of CXCR3, the cognate chemokine receptor for CXCL10, on hepatic B cells that remained in the liver post-mirtazapine. A significant role for CXCR3 in the hepatic retention of B cells post-mirtazapine was confirmed using CXCR3 receptor blockade. In addition, B cells remaining in the liver post-mirtazapine produced lower amounts of the proinflammatory Th1-like cytokines IFNγ, TNFα, and IL-6, and increased amounts of the Th2-like cytokine IL-4, after stimulation in vitro.ConclusionMirtazapine treatment rapidly alters hepatic B cell populations, enhancing hepatic retention of CXCR3-expressing innate-like B cells that generate a more anti-inflammatory cytokine profile. Mirtazapine-induced hepatic B cell shifts could potentially represent a novel therapeutic approach to immune-mediated liver diseases characterized by B cell driven pathology. | 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] Mirtazapine is an antidepressant drug, used to treat depression, but also, in some specific conditions, to treat obsessive-compulsive disorder and anxiety. Although mirtazapine is not a hypnotic, it can make the subject feel drowsy. Children under the age of 18 should not take mirtazapine, but for some very special diseases, a physician can prescribe it for a limited period of time. The authors report a case involving 2 children (7- and 9-year-old) who were administered mirtazapine without consent by the mother, who was under daily therapy with this antidepressant. Hair specimens, collected from the children were tested by liquid chromatography coupled to tandem mass spectrometry for mirtazapine and its metabolite, N-desmethylmirtazapine, on 3 × 1 cm segments. The hair test results (3 × 1 cm segments) have demonstrated that both children have been repetitively exposed to mirtazapine for approximately the last 3 months before hair collection, with concentrations in the range 1.32-3.79 and 0.64-2.54 ng/mg for mirtazapine and N-desmethylmirtazapine, respectively. Environmental contamination was ruled out as the measured concentrations are highly variable according to the pattern of drug distribution and the washes were negative. Hair testing for drugs appears as an excellent diagnostic tool for child protection toward drug exposure. | 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] While mirtazapine is primarily prescribed for major depressive disorder, it is less commonly prescribed for anorexia related to various disease states. Mirtazapine is associated with few adverse events but potential for a discontinuation syndrome does exist. Here we describe a case of a 53-year-old man prescribed mirtazapine 15 mg/day for appetite stimulation who experienced anxiousness, nausea, tremor, loss of appetite, lack of desire for food, and an 8-pound weight loss after abrupt, inadvertent discontinuation. Symptom onset was acute and presented within 48-hours of stopping his medication. Mirtazapine was restarted at the same dose after 14 days of ongoing symptoms and his symptoms subsided immediately. Scant literature exists to highlight the potentially serious adverse events associated with abrupt mirtazapine discontinuation, even at low doses, and this case contributes to advocating for the need of mirtazapine taper when medication cessation is being considered. | 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] We report a sudden death of an infant due to mirtazapine poisoning. A 15-day-old newborn boy was found dead when he was sleeping beside his mother who had suffered from panic disorder for approximately 1 year. After giving birth, she complained of palpitations and shaky hands, and was prescribed mirtazapine. The deceased newborn weighed 3,282 g and his height was 55 cm. There were no autopsy findings related to the death. The mirtazapine concentration as quantitated by liquid chromatography-tandem mass spectrometry analysis was 620 ng/mL in right heart blood, and was approximately 10 times higher than the therapeutic level in adults. Because transfer of mirtazapine into breast milk is low, mirtazapine was likely administered intentionally to the newborn. Based on the newborn's immature renal, liver, and blood-brain barrier function, the cause of death was attributed to mirtazapine poisoning. Poison-related homicide in the infant is rare. We report the first case of intentional mirtazapine poisoning case in a newborn. | Rissardo JP, Caprara ALF (2020) Mirtazapine-associated movement disorders: A literature review. Tzu chi medical journal 32, 318-330 [PubMed:33163376] [show Abstract] Mirtazapine (MTZ) is an atypical antidepressant approved by the FDA, which mechanism of action involves the antagonism of alpha-2, H1, 5-HT2A, 5-HT2C, and 5-HT3 receptors. In this context, the aim of this literature review is to evaluate the clinical epidemiological profile, pathological mechanisms, and management of MTZ-associated movement disorders (MDs). Relevant reports of six databases were identified and assessed by two reviewers without language restriction. Fifty-two reports containing 179 cases from 20 countries were assessed. The mean age was 57 year (range, 17-85). The majority of the individuals were female (60%) and of European origin. The mean time from MTZ start to symptom onset was 7.54 days; the time from management to MD improvement was within one week in 82.60% of the individuals. The MDs associated with MTZ were 69 restless legs syndrome (RLS), 35 tremors, 10 akathisia (AKT), 9 periodic limb MD, 6 dystonia, 4 rapid eye movement sleep behavior disorders, 3 dyskinesia, 2 parkinsonism, and 1 tic, and in the group not clearly identified, 18 restlessness, 15 hyperkinesis, and 1 extrapyramidal symptom. In the literature, the majority of the reports lack important information about the neurological examination. The management should be the MTZ withdrawal, except in RLS that other options are possible. In AKT, the MTZ should not be rechallenge, and if available, the prescription of a benzodiazepine may reduce recovery time. | 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]
ObjectiveMirtazapine is an a2A antagonist and mixed 5-HT2/5-HT3 antagonist that has been proposed as a potential treatment for obstructive sleep apnea (OSA). A small, randomized, controlled trial has previously found an approximate halving in the severity of OSA with daily doses of 4.5 and 15 mg. We aimed to confirm and extend these findings in 2 randomized placebo-controlled, proof-of-concept trials.MethodsTwo randomized, double-blind, placebo-controlled trials of mirtazapine for OSA (apnea-hypopnea index 10-40/h). Study 1: 3-way crossover, dose-finding study testing the self-administration of mirtazapine (7.5, 15, 30, and/or 45 mg) or placebo 30 minutes prior to bedtime for 2 weeks at each dose. Twenty patients were randomly assigned to 1 of 6 different dose-sequence groups, with each patient exposed to a maximum of 3 doses. Study 2: 3-arm, randomized, parallel-group trial of mirtazapine at 15 mg or mirtazapine 15 mg + Compound CD0012 or placebo for 4 weeks in 65 patients with OSA.ResultsTwo patients withdrew from Study 1 after complaints of unacceptable lethargy. Fifteen patients were withdrawn from study 2, 7 after complaints of unacceptable lethargy or other side-effects. No measurement of sleep apnea improved due to mirtazapine in either study. Weight gain was significantly greater on mirtazapine than on placebo in both trials.ConclusionsMirtazapine did not improve sleep apnea in either trial. Mirtazapine caused weight gain, which may further worsen OSA. Therefore, mirtazapine is not recommended for the treatment of OSA. | 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]
BackgroundMirtazapine is a novel piperazinoazepine antidepressant, unrelated to any known class of antidepressants. Currently, apart from a few case reports and case series in the literature, there are no studies evaluating the safety of this drug during pregnancy.ObjectiveTo determine whether mirtazapine increases the risk for major malformations in newborns when used by pregnant women.MethodThe study design was prospective, with 2 comparison groups: disease-matched pregnant women diagnosed with depression taking other antidepressants and pregnant women exposed to nonteratogens. The primary outcome was major malformations in neonates; secondary endpoints included spontaneous abortions, therapeutic abortions, gestational age at birth, and mean birth weight. Women were recruited from 5 teratogen information services in Toronto, Canada; Farmington, Conn., U.S.A.; Jerusalem, Israel; Rome, Italy; Sydney, Australia; and from the Drug Safety Research Unit in Southampton, United Kingdom. Women were recruited into the study from June 2002 to August 2005.ResultsWe were able to follow 104 pregnancy outcomes in each drug group. There were 77 live births, 1 stillbirth, 20 spontaneous abortions, 6 therapeutic abortions, and 2 major malformations in the mirtazapine group. The mean +/- SD birth weight was 3335 +/- 654 g and the mean +/- SD gestational age at delivery was 38.9 +/- 2.5 weeks. Most (95%) of the women took mirtazapine in the first trimester, but only 25% of the women took it throughout pregnancy. The differences among the 3 groups were in the rate of spontaneous abortions, which was higher in both antidepressant groups (19% in the mirtazapine group and 17% in the other antidepressant group) than in the nonteratogen group (11%), but none of the differences were statistically significant. The rate of preterm births (prior to 37 weeks' gestation) was also higher in the mirtazapine group (10%) and in the other antidepressant group (7%) than in the nonteratogen group (2%). The difference was statistically significant between the mirtazapine group and the nonteratogen group (p = .04).ConclusionMirtazapine does not appear to increase the baseline rate of major malformations of 1% to 3%. However, the higher number of spontaneous abortions in the antidepressant groups confirms the higher rates of spontaneous abortions in pregnant women taking antidepressant medications found in previous studies. | 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] There is currently available evidence that suggests that drugs combining 2 synergistic mechanisms of action (e.g., enhancement of both noradrenergic and serotonergic neurotransmission) may yield superior therapeutic efficacy compared with a single therapeutic mechanism of highly selective agents such as selective serotonin reuptake inhibitors (SSRIs). The differences in antidepressant efficacy favoring dual-acting drugs may exist in particular for 3 difficult-to-treat groups of patients: those with endogenous depression, those with severe depression, or hospitalized depressed patients. Mirtazapine differs from other new dual-acting antidepressants by not being a reuptake inhibitor. Its antidepressant activity may be related to a direct enhancement of noradrenergic neurotransmission by blockade of alpha2-autoreceptors. The rapid increase in serotonin (5-HT) synaptic levels by blockade of alpha2-heteroreceptors indirectly enhances 5-HT1A-mediated neurotransmission since 5-HT2 and 5-HT3 are blocked by mirtazapine. The antidepressant efficacy of mirtazapine was established in several placebo-controlled trials. Currently available evidence suggests that mirtazapine is effective in all levels of severity of depressive illness, as well as is in a broad range of symptoms associated with depression. |
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