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| Systematic (IUPAC) name | |
|---|---|
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(±)-2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
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| Clinical data | |
| Trade names | Remeron, Avanza, Axit, Mirtazon, Zispin |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a697009 |
| Licence data | US FDA:link |
| Pregnancy category |
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| Legal status |
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| Routes of administration |
Oral |
| Pharmacokinetic data | |
| Bioavailability | 50%[1][2][3][4] |
| Protein binding | 85%[1][2][3][4] |
| Metabolism | Liver (CYP1A2, CYP2D6 and CYP3A4)[1][2][3][4][5] |
| Biological half-life | 20–40 hours[1][2][3][4] |
| Excretion | Urine (75%)[1] Faeces (15%)[1][2][3][4] |
| Identifiers | |
| CAS Number | 61337-67-5 Y |
| ATC code | N06AX11 |
| PubChem | CID 4205 |
| IUPHAR/BPS | 7241 |
| DrugBank | DB00370 Y |
| ChemSpider | 4060 Y |
| UNII | A051Q2099Q N |
| KEGG | D00563 Y |
| ChEBI | CHEBI:6950 N |
| ChEMBL | CHEMBL654 Y |
| Synonyms | 6-Azamianserin, Org 3770 |
| Chemical data | |
| Formula | C17H19N3 |
| Molar mass | 265.35 g/mol |
| Chirality | 1 : 1 mixture (racemate) |
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SMILES
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InChI
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| Physical data | |
| Density | 1.22 g/cm3 |
| Melting point | 114 to 116 °C (237 to 241 °F) |
| Boiling point | 432 °C (810 °F) |
| Solubility in water | Soluble in methanol and chloroform mg/mL (20 °C) |
| NY (what is this?) (verify) | |
Mirtazapine (brand names: Avanza, Axit, Calixta, Mirtaz, Mirtazon, Remeron, Zispin)[6] is a noradrenergic and specific serotonergic antidepressant (NaSSA) introduced by Organon International in the United States in 1996,[2] and is used primarily in the treatment of depression. It is also commonly used as an anxiolytic, hypnotic, antiemetic and appetite stimulant. In structure, mirtazapine can also be classified as a tetracyclic antidepressant (TeCA) and is the 6-aza analogue of mianserin.[6] It is also racemic—occurs as a combination of both (R)- and (S)-stereoisomers, both of which are active.[6]
Its patent expired in 2004, so generic versions are available.[7]
Contents
- 1 Medical uses
- 1.1 Approved and off-label
- 1.2 Investigational
- 1.3 Feline and canine
- 1.4 Efficacy and tolerability
- 2 Adverse reactions
- 2.1 Side effects
- 2.2 Discontinuation
- 2.3 Overdose
- 3 Pharmacology
- 3.1 Binding profile
- 3.2 Correspondence to clinical effects
- 4 Pharmacokinetics
- 4.1 Dosage
- 4.2 Interactions
- 5 Chemistry
- 6 See also
- 7 References
- 8 Further reading
- 9 External links
Medical uses
Approved and off-label
Mirtazapine's primary use is the treatment of major depressive disorder and other mood disorders.[8][9]
However, it has also been found useful in alleviating the following conditions and may be prescribed off-label for their treatment:
- Generalized anxiety disorder[5][10]
- Social anxiety disorder[11][12]
- Obsessive-compulsive disorder[11][13]
- Panic disorder[11][14][15]
- Post-traumatic stress disorder[11]
- Low appetite/underweight[16][17][18]
- Insomnia[19][20]
- Nausea/vomiting[21][22][23]
- Itching[24][25]
- Headaches and migraine[22][26][27]
Investigational
Mirtazapine has had literature published on its efficacy in the experimental treatment of these conditions:
- Sleep apnoea/hypopnoea[28][29]
- Inappropriate sexual behaviour and other secondary symptoms of autistic spectrum conditions and other pervasive developmental disorders[30][31][32][33]
- Antipsychotic-induced akathisia[34][35]
- Drug withdrawal, dependence and detoxification[36]
- Negative, depressive and cognitive symptoms of schizophrenia (as an adjunct)[37][38]
- A case report has been published in which mirtazapine reduced visual hallucinations in a patient with Parkinson's disease psychosis (PDP).[39] This is in alignment with recent findings that inverse agonists at the 5-HT2A receptors are efficacious in attenuating the symptoms of Parkinson's disease psychosis. As is supported by the common practice of prescribing low-dose quetiapine and clozapine for PDP—doses too low to antagonise the D2 receptor, but sufficiently high doses to inversely agonise the 5-HT2A receptors.[40]
Feline and canine
Mirtazapine is sometimes prescribed as an appetite stimulant for cats or dogs experiencing anorexia due to medical conditions such as chronic kidney disease. It is especially useful for treating combined poor appetite and nausea in cats and dogs.[41][42]
Efficacy and tolerability
In clinical studies, mirtazapine has been found to be an effective antidepressant with a generally tolerable side-effect profile relative to other antidepressants.[43]
In a major meta-analysis published in 2009 that compared the efficacy and tolerability of 12 second-generation antidepressants, mirtazapine was found to be superior to all of the included selective serotonin reuptake inhibitors (SSRIs), serotonin-norepinephrine reuptake inhibitors (SNRIs), reboxetine and bupropion in terms of antidepressant efficacy, while it was average in regard to tolerability.[43] However, its superior efficacy over the other medications in the top four (escitalopram, sertraline and venlafaxine) did not reach statistical significance.[43]
Compared to earlier antidepressants, mirtazapine has been found to be significantly superior to trazodone,[44] while it has been shown to be approximately equivalent in efficacy to several of the tricyclic antidepressants including amitriptyline, doxepin and clomipramine, though with a much improved tolerability profile.[5][45] However, two other studies found mirtazapine to be significantly inferior to imipramine, another TCA.[46][47] One study compared the combination of venlafaxine and mirtazapine to the monoamine oxidase inhibitor (MAOI) tranylcypromine alone and found them to be similarly effective, though tranylcypromine was much less tolerable in regard to side effects and drug interactions.[48]
In general, all antidepressants, including mirtazapine, require at least a week for their therapeutic benefits on depressive and anxious symptoms to become apparent.[49][50] Mirtazapine has a faster onset of antidepressant action when compared to SSRIs, with an initial reduction in affective symptoms being seen within the first week of treatment, and the maximal change in improvement occurring over the course of the first two weeks, however ingesting small doses sporadically can cause some of the same short term side effects as opiates such as minor pain relief as well as constricting of the pupils.[49][51]
Adverse reactions
A box of Mirtazapine-Sandoz
Side effects
Information sources:[2][3][4][52][53][54]
- Very common (≥10% incidence) adverse effects
- Constipation (13%)
- Dry mouth (25%)
- Increased appetite (17%)
- Somnolence (54%), sedation, sleepiness
- Weight gain (≥7% weight gain, only in pediatrics is this very common)
- Weight gain (≥7% weight gain, in 8% of adult trial participants)
- Common (1%≤ incidence <10%) adverse effects
- ALT (SGPT) level raised (2%)
- Asthenia (8%)
- Disturbance in thinking (3%)
- Dizziness (7%)
- Peripheral oedema
- Serum triglycerides raised (increases to 500 mg/dL (5,65 mmol/L) or greater: 6%)
- Uncommon (0.1%≤ incidence <1%)
- Headache
- Rare (incidence <0.1%)
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- Unknown frequency
- Diarrhea
- Nausea
Mirtazapine is not considered to have a risk of many of the side effects often associated with other antidepressants like the SSRIs, and may actually improve certain ones when taken in conjunction with them.[5][45] These adverse effects include decreased appetite, weight loss, insomnia, nausea and vomiting, diarrhoea, urinary retention, increased body temperature, excessive sweating, pupil dilation and sexual dysfunction.[5][45]
In general, some antidepressants, especially SSRIs, can paradoxically exacerbate some peoples' depression or anxiety or cause suicidal ideation.[55] Despite its sedating action, mirtazapine is also believed to be capable of this, so in the United States and certain other countries, it carries a black box label warning of these potential effects.
Discontinuation
Mirtazapine and other antidepressants may cause a withdrawal syndrome upon discontinuation.[5][56][57] A gradual and slow reduction in dose is recommended to minimize withdrawal symptoms.[58] Effects of sudden cessation of treatment with mirtazapine may include depression, anxiety, panic attacks, vertigo, restlessness, irritability, decreased appetite, insomnia, diarrhoea, nausea, vomiting, flu-like symptoms such as allergies and pruritus, headaches and sometimes hypomania or mania.[56][59][60][61][62]
Overdose
Mirtazapine is considered to be relatively safe in the event of an overdose,[50] although it is considered slightly more toxic in overdose than most of the SSRIs (except citalopram).[63] Unlike the TCAs, mirtazapine showed no significant cardiovascular adverse effects at 7 to 22 times the maximum recommended dose.[45] Case reports of overdose with as much as 30 to 50 times the standard dose described the drug as relatively nontoxic, compared to TCAs.[64][65]
Twelve reported fatalities have been attributed to mirtazapine overdose.[66][67] The fatal toxicity index (deaths per million prescriptions) for mirtazapine is 3.1 (95% CI: 0.1 to 17.2). This is similar to that observed with SSRIs.[68]
Pharmacology
Binding profile
Mirtazapine is an antagonist/inverse agonist at the following receptors:[69][70]
| Molecular target | Binding affinity, Ki (nM)[71] | Notes |
|---|---|---|
| 5-HT2A receptor | 69 | The (S)-(+) enantiomer is responsible for this antagonism.[6] |
| 5-HT2B receptor | ? | ~20-fold lower than for 5-HT2A/5-HT2C[72] |
| 5-HT2C receptor | 39 | Inverse agonist[73] The (S)-(+) enantiomer is responsible for this action.[6] |
| 5-HT3 receptor | ? | Similar to 5-HT2A/5-HT2C (mouse neuroblastoma cell)[74] R-(–) enantiomer antagonises the 5-HT3 receptor.[6] |
| 5-HT7 receptor | 265 | |
| α1-adrenergic receptor | 500 | [75] |
| α2A-adrenergic receptor | 20 | The S-(+) enantiomer is responsible for this antagonism at autoreceptors.[6] Heteroreceptors are blocked by both the (S)-(+) and (R)-(–) enantiomers.[3] |
| α2C-adrenergic receptor | 18 | The S-(+) enantiomer is responsible for this antagonism at autoreceptors.[6] Heteroreceptors are blocked by both the (S)-(+) and (R)-(–) enantiomers.[3] |
| D1 receptor | 4167 | |
| D2 receptor | >5454 | |
| D3 receptor | 5723 | |
| H1 receptor | 1.6 | [76] |
| mACh receptors | 670 | [75] |
All affinities listed were assayed using human materials except those for α1-adrenergic and mACh that are for rat tissues, due to human values being unavailable.[69][70]
Mirtazapine has recently been found to act as a weak (EC50 7.2 μM) κ-opioid receptor partial agonist.[77]
Correspondence to clinical effects
Antagonization of the α2-adrenergic receptors, which function largely as autoreceptors and heteroreceptors enhances adrenergic and serotonergic neurotransmission, the notable ones being central 5-HT1A receptor-mediated transmission in the dorsal raphe nucleus and hippocampus; hence, mirtazapine's classification as a NaSSA. Indirect α1-adrenoceptor-mediated enhancement of 5-HT cell firing and direct blockade of inhibitory α2-heteroreceptors located on 5-HT terminals are held responsible for the increase in extracellular 5-HT.[5][8][78][79][80] Because of this, mirtazapine has been said to be a functional "indirect agonist" of the 5-HT1A receptor.[79] Increased activation of the central 5-HT1A receptor is thought to be a major mediator of efficacy of most antidepressant drugs.[81] Unlike most conventional antidepressants, however, at clinically used doses mirtazapine has no appreciable affinity for the serotonin, norepinephrine, or dopamine transporters and thus lacks any significant effects as a reuptake inhibitor of these neurotransmitters,[82] nor does it have any significant inhibitory effects on monoamine oxidase.[83]
Antagonism of the 5-HT2 subfamily of receptors and inverse agonism of the 5-HT2C receptor appears to be in part responsible for mirtazapine's efficacy in the treatment of depressive states.[84][85] The 5-HT2C receptor is known to inhibit the release of the neurotransmitters dopamine and norepinephrine in various parts of the brains of rodents, notably in reward pathways such as the ventral tegmental area.[86][87] Accordingly, it was shown that by blocking the α2-adrenergic receptors and 5-HT2C receptors mirtazapine disinhibited dopamine and norepinephrine activity in these areas in rats.[88] In addition, mirtazapine's antagonism of 5-HT2A receptors has beneficial effects on anxiety, sleep and appetite, as well as sexual function regarding the latter receptor.[5][45] The newest research however has shown that mirtazapine is actually an inverse agonist of the 5-HT2C receptor. 5-HT2C inverse agonists have been shown to inhibit mesoaccumbens dopamine outflow[89] attenuating the rewarding properties of various substances like morphine. This inhibition of dopamine may be stronger than thought as substances with 5-HT2C inverse agonist properties may have more activity to regulate dopamine neurotransmission than ones with competitive antagonism.[90] With its newly understood properties of 5-HT2C inverse agonism, it is being investigated and shown to lower drug seeking behaviour, conditioned place preference and the rewarding effects of substances such as methamphetamine in various human and animal studies.[73][91][92] It is also being investigated to help in substance abuse disorders with withdrawal effects and remission rates.[73][93] but some studies have shown mixed benefit.[73][94][95]
Antagonism of the 5-HT3 receptor, an action mirtazapine shares with the approved antiemetic ondansetron, significantly improves pre-existing symptoms of nausea, vomiting, diarrhea, and irritable bowel syndrome in afflicted individuals.[96] Mirtazapine may be used as an inexpensive antiemetic alternative to ondansetron.[23] Blockade of the 5-HT3 receptors has also shown to improve anxiety and to be effective in the treatment of drug addiction in several studies.[97] In conjunction with substance abuse counseling, mirtazapine has been investigated for the purpose of reducing methamphetamine use in dependent individuals with success.[91] In contrast to mirtazapine, the SSRIs, SNRIs, MAOIs, and some TCAs increase the general activity of the 5-HT2A, 5-HT2C, and 5-HT3 receptors leading to a host of negative changes and side-effects, the most prominent of which including anorexia, insomnia, sexual dysfunction (loss of libido and anorgasmia), nausea, and diarrhoea, among others. As a result, it is often combined with these drugs to reduce their side-effect profile and to produce a stronger antidepressant effect.[45][48][98][99][100][101]
Mirtazapine is a very strong H1 receptor inverse agonist and, as a result, it can cause powerful sedative and hypnotic effects.[5] After a short period of chronic treatment, however, the H1 receptor tends to desensitize and the antihistamine effects become more tolerable. Many patients may also dose at night to avoid the effects, and this appears to be an effective strategy for combating them. Blockade of the H1 receptor may improve pre-existing allergies, pruritus, nausea, and insomnia in afflicted individuals. It may also contribute to weight gain, however.[102] In contrast to the H1 receptor, mirtazapine has very low affinity for the mACh receptors, although anticholinergic side effects like dry mouth, constipation, and mydriasis are still commonly seen in clinical practise.[103]
Like many other antidepressants, mirtazapine has been found to have antinociceptive properties in mice.[104] However, unlike most other antidepressants, though similarly to venlafaxine, these effects are mostly mediated through downstream modulation of the endogenous opioid system, of which in the case of mirtazapine the μ-opioid and κ3-opioid receptors are mainly involved.[104] Interestingly, while virtually all antidepressants differ little in their maximal effectiveness in the treatment of major depression, mirtazapine and venlafaxine have demonstrated superior efficacy in treating severe types of depression such as psychotic depression and treatment-resistant depression.[104] This may be due to their unique influence on the opioid system, which is a property that may give them an advantage over other antidepressants in cases of severe depressive symptomatology.[104]
Pharmacokinetics
The (S)-(+)-enantiomer has a plasma half-life of 9.9±3 hours and the (R)-(–)-enantiomer has a plasma half-life of 18±2.5 hours.[1] The overall elimination half-life is 20–40 hours.
Dosage
Mirtazapine is typically prescribed in doses for humans of 15, 30 and 45 mg. However, clinical doses as high as 120 mg have been reported in the medical literature.[105]
Interactions
Concurrent use with inhibitors or inducers of the cytochrome (CYP) P450 isoenzymes CYP1A2, CYP2D6, and/or CYP3A4 can result in altered concentrations of mirtazapine, as these are the main enzymes responsible for its metabolism.[1][5] As examples, fluoxetine and paroxetine, inhibitors of these enzymes, are known to modestly increase mirtazapine levels, while carbamazepine, an inducer, considerably decreases them.[1]
According to information from the manufacturers, mirtazapine should not be started within two weeks of any MAOI usage; likewise, MAOIs should not be administered within two weeks of discontinuing mirtazapine.[106] However, a single study regarding the combination reported it does not result in any incidence of serotonin-related toxicity.[107] In addition, a case report claimed that mirtazapine can actually be used to treat serotonin syndrome.[108] Mirtazapine in combination with an SSRI, SNRI, or TCA as an augmentation strategy is considered to be relatively safe and is often employed therapeutically,[45][48][98][99][100] with a combination of venlafaxine and mirtazapine sometimes referred to as “California rocket fuel”.[109]
Another case report described mirtazapine as inducing hypertension in a clonidine-treated patient, likely due to occupancy of α2-autoreceptors by mirtazapine limiting the efficacy of concurrent clonidine therapy.[110]
Liver and moderate renal impairment have been reported to decrease the oral clearance of mirtazapine by about 30%; severe renal impairment decreases it by 50%.[1]
Chemistry
Mirtazapine is a racemic mixture of enantiomers. The (S)-(+)-enantiomer is known as esmirtazapine.
A four-step chemical synthesis of mirtazapine has been published.[111][112]
See also
- Aptazapine
- Mianserin
- Setiptiline
References
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- ^ a b Ravindran LN, Eisfeld BS, Kennedy SH (Feb 2008). "Combining mirtazapine and duloxetine in treatment-resistant depression improves outcomes and sexual function". Journal of Clinical Psychopharmacology 28 (1): 107–8. doi:10.1097/JCP.0b013e318160d609. PMID 18204355. [unreliable medical source?]
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- ^ Burrows GD, Kremer CM (Apr 1997). "Mirtazapine: clinical advantages in the treatment of depression". Journal of Clinical Psychopharmacology. 17 Suppl 1: 34S–39S. doi:10.1097/00004714-199704001-00005. PMID 9090576.
- ^ a b c d Schreiber S, Bleich A, Pick CG (2002). "Venlafaxine and mirtazapine: different mechanisms of antidepressant action, common opioid-mediated antinociceptive effects--a possible opioid involvement in severe depression?". Journal of Molecular Neuroscience 18 (1-2): 143–9. doi:10.1385/JMN:18:1-2:143. PMID 11931344.
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- ^ Mirtazapine monograph
- ^ Gillman PK (Jun 2006). "A review of serotonin toxicity data: implications for the mechanisms of antidepressant drug action". Biological Psychiatry 59 (11): 1046–51. doi:10.1016/j.biopsych.2005.11.016. PMID 16460699.
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- ^ US patent 4062848, Van der Burg WJ, "Tetracyclic compounds", published 1977-12-13, issued 1977-12-13
Further reading
- Stimmel GL, Dopheide JA, Stahl SM (1997). "Mirtazapine: an antidepressant with noradrenergic and specific serotonergic effects". Pharmacotherapy 17 (1): 10–21. doi:10.1002/j.1875-9114.1997.tb03674.x. PMID 9017762.
- Anttila SA, Leinonen EV (2001). "A review of the pharmacological and clinical profile of mirtazapine". CNS Drug Reviews 7 (3): 249–64. doi:10.1111/j.1527-3458.2001.tb00198.x. PMID 11607047.
External links
- Mirtazapine - Drugs.com
- Remeron - Rxlist.com
- Mirtazapine - MedicineNet.com
- Mirtazapine - MedlinePlus
- Mirtazapine - About.com
- U.S. National Library of Medicine: Drug Information Portal - Mirtazapine
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UpToDate Contents
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- 1. 成人の精神刺激薬使用障害への薬物療法 pharmacotherapy for stimulant use disorders in adults
- 2. 非定型抗うつ薬：薬理学、投与方法、および副作用 atypical antidepressants pharmacology administration and side effects
- 3. 癌における食欲不振および悪液質の薬理学的マネージメント pharmacologic management of cancer anorexia cachexia
- 4. 妊娠中の抗うつ薬のリスク：選択的セロトニン再取り込み阻害剤以外の薬剤 risks of antidepressants during pregnancy drugs other than selective serotonin reuptake inhibitors
- 5. 進行性多巣性白質脳症：治療および予後 progressive multifocal leukoencephalopathy treatment and prognosis
English Journal
- Validation of a dried blood spot method for therapeutic drug monitoring of citalopram, mirtazapine and risperidone and its active metabolite 9-hydroxyrisperidone using HPLC-MS.
- Weber J1, Oberfeld S2, Bonse A2, Telger K3, Lingg R4, Hempel G5.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2017 Jun 5;140:347-354. doi: 10.1016/j.jpba.2017.02.061. Epub 2017 Mar 27.
- PMID 28395245
- Treatment options for hyperemesis gravidarum.
- Abramowitz A1, Miller ES2, Wisner KL2.
- Archives of women's mental health.Arch Womens Ment Health.2017 Jun;20(3):363-372. doi: 10.1007/s00737-016-0707-4. Epub 2017 Jan 9.
- PMID 28070660
- Reversing glioma malignancy: a new look at the role of antidepressant drugs as adjuvant therapy for glioblastoma multiforme.
- Bielecka-Wajdman AM1, Lesiak M2, Ludyga T3, Sieroń A2, Obuchowicz E3.
- Cancer chemotherapy and pharmacology.Cancer Chemother Pharmacol.2017 Jun;79(6):1249-1256. doi: 10.1007/s00280-017-3329-2. Epub 2017 May 12.
- PMID 28500556
Japanese Journal
- レメロン(新薬のプロフィル)
- ファルマシア 46(2), 156-157, 2010-02-01
- NAID 110009891076
Related Links
- MSD株式会社のレメロン錠15mg（中枢神経用薬）、一般名ミルタザピン(Mirtazapine) の効果と副作用、写真、保管方法等を掲載。 ... レメロン錠15mg 薬には効果（ベネフィット）だけでなく副作用（リスク）があります。副作用をなるべく ...
- レメロン,リフレックスとは?ミルタザピンの効能,副作用等を説明,ジェネリックや薬価も調べられる(おくすり110番:薬事典版) ... 成分（一般名） ： ミルタザピン 製品例 ： レメロン錠15mg、リフレックス錠15mg ・・その他(ジェネリック) & 薬価
Related Pictures
★リンクテーブル★
| リンク元 | 「ミルタザピン」 |
「ミルタザピン」
特徴
- ノルアドレナリン作動性・特異的セロトニン作動性抗うつ薬
- シナプス前部の自己受容体のα2受容体を阻害し、セロトニン・ノルアドレナリン放出を促進。立ち上がりが早く、胃腸症状や性機能障害が少ない。
適応
- うつ病、うつ状態
禁忌
- 1. 本剤の成分に対して過敏症の既往歴のある患者
- 2. MAO阻害剤を投与中あるいは投与中止後２週間以内の患者
副作用
- うつ病・うつ状態の患者を対象とした国内臨床試験において、総症例330例中273例（82.7％）、914件に臨床検査値を含む副作用が報告された。その主なものは傾眠165例（50.0％）、口渇68例（20.6％）、倦怠感50例（15.2％）、便秘42例（12.7％）、アラニン・アミノトランスフェラーゼ増加41例（12.4％）であった（承認時）。
添付文書
- レメロン錠
- リフレックス錠15mg