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Mirtazapine information


Mirtazapine
Clinical data
Trade namesRemeron, Mirataz, Avanza, others
Other namesMepirzapine; 6-Azamianserin; ORG-3770[1][2]
AHFS/Drugs.comMonograph
MedlinePlusa697009
License data
  • US DailyMed: Mirtazapine
Pregnancy
category
  • AU: B3[3]
Routes of
administration
By mouth (tablets), topical
Drug classNoradrenergic and specific serotonergic antidepressant (NaSSA)
ATC code
  • N06AX11 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[5]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[4]Rx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability50%[6][7][8][9]
Protein binding85%[6][7][8][9]
MetabolismLiver (CYP1A2, CYP2D6, CYP3A4)[6][7][8][9][10]
MetabolitesDesmethylmirtazapine (contributes 3–10% of activity)[10][6]
Elimination half-life20–40 hours[6][7][8][9]
ExcretionUrine: 75%[6]
Feces: 15%[6][7][8][9]
Identifiers
IUPAC name
  • (±)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
CAS Number
  • 85650-52-8 checkY
PubChem CID
  • 4205
IUPHAR/BPS
  • 7241
DrugBank
  • DB00370 checkY
ChemSpider
  • 4060 checkY
UNII
  • A051Q2099Q
KEGG
  • D00563 checkY
ChEBI
  • CHEBI:6950 checkY
ChEMBL
  • ChEMBL654 checkY
CompTox Dashboard (EPA)
  • DTXSID0023325 Edit this at Wikidata
ECHA InfoCard100.080.027 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3
Molar mass265.360 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
Density1.22 g/cm3
Melting point114 to 116 °C (237 to 241 °F)
Boiling point432 °C (810 °F)
Solubility in waterSoluble in methanol and chloroform mg/mL (20 °C)
SMILES
  • n1cccc3c1N4C(c2ccccc2C3)CN(C)CC4
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 checkY
  • Key:RONZAEMNMFQXRA-UHFFFAOYSA-N checkY
  (verify)

Mirtazapine, sold under the brand name Remeron among others, is an atypical tetracyclic antidepressant, and as such is used primarily to treat depression.[10][11] Its effects may take up to four weeks, but can also manifest as early as one to two weeks.[11][12] It is often used in cases of depression complicated by anxiety or insomnia.[10][13] The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants.[14] It is taken by mouth.[11]

Common side effects include sleepiness, dizziness, increased appetite and weight gain.[11] Serious side effects may include mania, low white blood cell count, and increased suicide among children.[11] Withdrawal symptoms may occur with stopping.[15] It is not recommended together with a monoamine oxidase inhibitor,[11] although evidence supporting the danger of this combination has been challenged.[16] It is unclear if use during pregnancy is safe.[11] How it works is not clear, but it may involve blocking certain adrenergic and serotonin receptors.[10][11] Chemically, it is a tetracyclic antidepressant,[11] and is closely related to mianserin. It also has strong antihistaminergic effects.[10][11]

Mirtazapine came into medical use in the United States in 1996.[11] The patent expired in 2004, and generic versions are available.[11][17] In 2021, it was the 124th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[18][19]

  1. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  3. ^ "Mirtazapine Use During Pregnancy". Drugs.com. 23 September 2019. Archived from the original on 22 August 2020. Retrieved 4 March 2020.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  6. ^ a b c d e f g Timmer CJ, Sitsen JM, Delbressine LP (June 2000). "Clinical pharmacokinetics of mirtazapine". Clinical Pharmacokinetics. 38 (6): 461–474. doi:10.2165/00003088-200038060-00001. PMID 10885584. S2CID 27697181.
  7. ^ a b c d e "REMERON (mirtazapine) tablet, film coated [Organon Pharmaceuticals USA]". DailyMed. Organon Pharmaceuticals USA. October 2012. Archived from the original on 10 January 2021. Retrieved 24 October 2013.
  8. ^ a b c d e Cite error: The named reference AXIT was invoked but never defined (see the help page).
  9. ^ a b c d e Cite error: The named reference EMC was invoked but never defined (see the help page).
  10. ^ a b c d e f Anttila SA, Leinonen EV (2001). "A review of the pharmacological and clinical profile of mirtazapine". CNS Drug Reviews. 7 (3): 249–264. doi:10.1111/j.1527-3458.2001.tb00198.x. PMC 6494141. PMID 11607047.
  11. ^ a b c d e f g h i j k l "Mirtazapine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 10 January 2021. Retrieved 20 November 2018.
  12. ^ Cite error: The named reference Cochrane2011 was invoked but never defined (see the help page).
  13. ^ Nutt DJ (June 2002). "Tolerability and safety aspects of mirtazapine". Human Psychopharmacology. 17 (Suppl 1): S37–S41. doi:10.1002/hup.388. PMID 12404669. S2CID 23699759.
  14. ^ "[129] Mirtazapine: Update on efficacy, safety, dose response". www.ti.ubc.ca. Archived from the original on 7 May 2021. Retrieved 8 May 2021.
  15. ^ British national formulary : BNF 74 (74 ed.). British Medical Association. 2017. p. 354. ISBN 978-0857112989.
  16. ^ Cite error: The named reference pmid16342227 was invoked but never defined (see the help page).
  17. ^ Schatzberg AF, Cole JO, DeBattista C (2010). "3". Manual of Clinical Psychopharmacology (7th ed.). Arlington, VA: American Psychiatric Publishing. ISBN 978-1-58562-377-8.
  18. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  19. ^ "Mirtazapine - Drug Usage Statistics". ClinCalc. Archived from the original on 20 October 2020. Retrieved 14 January 2024.

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Mirtazapine

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Tetracyclic antidepressant

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classified as a TCA and grouped with the secondary amines Mianserin (Tolvon) Mirtazapine (Remeron) Setiptiline (Tecipul) Drugs that contain four rings not all...

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Esmirtazapine

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associated with menopause. Esmirtazapine is the (S)-(+)-enantiomer of mirtazapine and possesses similar overall pharmacology, including inverse agonist...

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Mianserin

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a tetracyclic antidepressant (TeCA). Mianserin is closely related to mirtazapine, both chemically and in terms of its actions and effects, although there...

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Antidepressants in Japan

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approval of mirtazapine in Japan, a drug on the market in many Western countries since 1994. Meiji Seika is commercializing mirtazapine (brand name Reflex)...

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Antiemetic

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(Benadryl) Dimenhydrinate (Gravol, Dramamine) Doxylamine (Bonjesta, Unisom) Mirtazapine (Remeron) is an antidepressant that also has antiemetic effects. It is...

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Akathisia

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if the akathisia was caused by an antipsychotic. The antidepressant mirtazapine has demonstrated benefit, but is also known to have caused akathisia...

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Appetite stimulant

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agonists — mirtazapine, olanzapine, quetiapine, amitriptyline, cyproheptadine, lurasidone H1 receptor antagonists/inverse agonists — mirtazapine, olanzapine...

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Atypical antidepressant

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antidepressants include agomelatine, bupropion, iprindole, mianserin, mirtazapine, nefazodone, opipramol, tianeptine, and trazodone. The agents vilazodone...

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Somnolence

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– for instance, sedating tricyclic antidepressants Amitriptyline and mirtazapine. Somnolence is less common with SSRIs and SNRIs as well as MAOIs. Antihistamines...

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Miosis

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Zofran Some cancer chemotherapy drugs, including camptothecin derivatives Mirtazapine, a noradrenergic and specific serotonergic antidepressant (NaSSA) Some...

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Serotonin receptor antagonist

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irritable bowel syndrome: Alosetron Cilansetron Also, the antidepressant mirtazapine acts as a 5-HT3 antagonist. Although some non-selective serotonin antagonists...

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Tetracyclic

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tetracyclic antidepressants Benzoctamine Loxapine Mazindol Mianserin Mirtazapine Tricyclic Heterocyclic Wheatley, David (1982-05-01). "A new weight-reducing...

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List of antidepressants

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Maprotiline (Ludiomil) Mianserin (Tolvon) Mirtazapine (Remeron) Setiptiline (Tecipul) Mianserin, mirtazapine, and setiptiline are also sometimes described...

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Hypnotic

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medicines off-label if they have sedating effects. Examples of these include mirtazapine (an antidepressant), clonidine (an older antihypertensive drug), quetiapine...

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Rilmenidine

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Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil...

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Oneirogen

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and Ramelteon may cause vivid dreams as a side effect[citation needed] Mirtazapine, paroxetine, and varenicline often cause vivid dreams. [citation needed]...

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MDMA

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(e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics...

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Arthralgia

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Ketamine

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Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide...

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Fentanyl

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Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH Nalfurafine Nalmefene...

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List of psychiatric medications

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Methaqualone

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Antihistamine

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commonly used as an antiemetic) Mianserin (tetracyclic antidepressant) Mirtazapine (tetracyclic antidepressant, also has antiemetic and appetite-stimulating...

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nimetazepam for this purpose. Antidepressants such as trazodone and mirtazapine or Z-drugs like zopiclone and zolpidem are first line treatment for insomnia...

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