Mirtazapine

Mirtazapine
Clinical data
Trade namesRemeron, Mirataz, Avanza, others
Other namesMepirzapine; 6-Azamianserin; ORG-3770[1][2]
AHFS/Drugs.comMonograph
MedlinePlusa697009
License data
Pregnancy
category
Routes of
administration		By mouth, topical
Drug classNoradrenergic and specific serotonergic antidepressant (NaSSA)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability50%[8][6][9][10]
Protein binding85%[8][6][9][10]
MetabolismLiver (CYP1A2, CYP2D6, CYP3A4)[8][6][9][10][11]
MetabolitesDesmethylmirtazapine (contributes 3–10% of activity)[11][8]
Elimination half-life20–40 hours[8][6][9][10]
ExcretionUrine: 75%[8]
Feces: 15%[8][6][9][10]
Identifiers
  • (±)-5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.080.027 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3
Molar mass265.360 g·mol−1
3D model (JSmol)
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)
  • n1cccc3c1N4C(c2ccccc2C3)CN(C)CC4
  • 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.[11][12] Its effects may take up to four weeks but can also manifest as early as one to two weeks.[12][13] It is often used in cases of depression complicated by anxiety or insomnia.[11][14] The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants.[15] It is taken by mouth.[12]

Common side effects include sleepiness, dizziness, increased appetite and weight gain.[12] Serious side effects may include mania, low white blood cell count, and increased suicide among children.[12] Withdrawal symptoms may occur with stopping.[16] It is not recommended together with a monoamine oxidase inhibitor,[12] although evidence supporting the danger of this combination has been challenged.[17] It is unclear if use during pregnancy is safe.[12] How it works is not clear, but it may involve blocking certain adrenergic and serotonin receptors.[11][12] Chemically, it is a tetracyclic antidepressant,[12] and is closely related to mianserin. It also has strong antihistaminergic effects.[11][12]

Mirtazapine came into medical use in the United States in 1996.[12] The patent expired in 2004, and generic versions are available.[12][18] In 2022, it was the 105th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[19][20]

  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 "Remeron- mirtazapine tablet, film coated; Remeronsoltab- mirtazapine tablet, orally disintegrating". DailyMed. 4 March 2024. Retrieved 1 September 2024.
  7. ^ "Mirataz- mirtazapine ointment". DailyMed. 5 April 2024. Retrieved 1 September 2024.
  8. ^ 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.
  9. ^ a b c d e Cite error: The named reference AXIT was invoked but never defined (see the help page).
  10. ^ a b c d e Cite error: The named reference EMC was invoked but never defined (see the help page).
  11. ^ 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.
  12. ^ 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.
  13. ^ Cite error: The named reference Cochrane2011 was invoked but never defined (see the help page).
  14. ^ 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.
  15. ^ "[129] Mirtazapine: Update on efficacy, safety, dose response". www.ti.ubc.ca. Archived from the original on 7 May 2021. Retrieved 8 May 2021.
  16. ^ British national formulary : BNF 74 (74 ed.). British Medical Association. 2017. p. 354. ISBN 978-0857112989.
  17. ^ Cite error: The named reference pmid16342227 was invoked but never defined (see the help page).
  18. ^ 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.
  19. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  20. ^ "Mirtazapine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.