Memantine

Memantine
Clinical data
Trade namesAxura, Ebixa, Namenda, others[1][2]
Other names1-Amino-3,5-dimethyladamantane; 3,5-Dimethyladamantan-1-amine; Dimethyladamantanamine; DMAA; D145; D-145
AHFS/Drugs.comMonograph
MedlinePlusa604006
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth
Drug classNMDA receptor antagonist
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • UK: POM (Prescription only)[4]
  • US: ℞-only[5][6]
  • EU: Rx-only[7]
Pharmacokinetic data
Bioavailability100%[8][9]
Protein binding45%[8][9]
MetabolismMinimal[9]
Metabolites• Memantine glucuronide[8][9]
• 6-Hydroxymemantine[8][9]
• 1-Nitrosomemantine[8][9]
Elimination half-life60–80 hours[8][9]
ExcretionUrine (57–82% unchanged)[8][9]
Identifiers
IUPAC name
  • 3,5-dimethyltricyclo[3.3.1.13,7]decan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.217.937
Chemical and physical data
FormulaC12H21N
Molar mass179.307 g·mol−1
3D model (JSmol)
SMILES
  • NC12CC3CC(C)(C1)CC(C)(C3)C2

  • as HCl: Cl.NC12CC3CC(C)(C1)CC(C)(C3)C2
InChI
  • InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3 Y
  • Key:BUGYDGFZZOZRHP-UHFFFAOYSA-N Y

  • as HCl: InChI=1S/C12H21N.ClH/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10;/h9H,3-8,13H2,1-2H3;1H
  • Key:LDDHMLJTFXJGPI-UHFFFAOYSA-N
  (verify)

Memantine, sold under the brand name Namenda among others, is a medication used to slow the progression of moderate-to-severe Alzheimer's disease.[10][11][8] It is taken by mouth.[10][8]

Common side effects include headache, constipation, sleepiness, and dizziness.[10][11] Severe side effects may include blood clots, psychosis, and heart failure.[11] It is believed to work by acting on NMDA receptors, working as a pore blocker of these ion channels.[8][10]

Memantine was first discovered in 1963.[8][12][13] It was approved for medical use in Germany in 1989, in the European Union in 2002, and in the United States in 2003.[13][10][14] It is available as a generic medication.[11] In 2022, it was the 150th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[15][16]

  1. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 753. ISBN 978-3-88763-101-7. Retrieved 12 September 2024.
  3. ^ 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.
  4. ^ "Ebixa 10 mg film-coated tablets Summary of Product Characteristics (SmPC)". (emc). 13 December 2021. Retrieved 2 May 2024.
  5. ^ "Namenda- memantine hydrochloride tablet; Namenda- memantine hydrochloride kit". DailyMed. 1 November 2018. Retrieved 2 May 2024.
  6. ^ "Namenda XR- memantine hydrochloride capsule, extended release; Namenda XR- memantine hydrochloride kit". DailyMed. 15 November 2019. Retrieved 2 May 2024.
  7. ^ "Axura EPAR". European Medicines Agency (EMA). 17 May 2002. Retrieved 27 February 2024.
  8. ^ a b c d e f g h i j k Alam S, Lingenfelter KS, Bender AM, Lindsley CW (September 2017). "Classics in Chemical Neuroscience: Memantine". ACS Chem Neurosci. 8 (9): 1823–1829. doi:10.1021/acschemneuro.7b00270. PMID 28737885.
  9. ^ a b c d e f g h Schmitt F, Ryan M, Cooper G (February 2007). "A brief review of the pharmacologic and therapeutic aspects of memantine in Alzheimer's disease". Expert Opin Drug Metab Toxicol. 3 (1): 135–141. doi:10.1517/17425255.3.1.135. PMID 17269900.
  10. ^ a b c d e "Memantine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 25 April 2019. Retrieved 3 March 2019.
  11. ^ a b c d British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 303–304. ISBN 9780857113382.
  12. ^ del Río-Sancho S (2020). "Memantine and Alzheimer's disease". Diagnosis and Management in Dementia. Elsevier. pp. 511–527. doi:10.1016/b978-0-12-815854-8.00032-x. ISBN 978-0-12-815854-8.
  13. ^ a b Herrmann N, Li A, Lanctôt K (April 2011). "Memantine in dementia: a review of the current evidence". Expert Opinion on Pharmacotherapy. 12 (5): 787–800. doi:10.1517/14656566.2011.558006. PMID 21385152.
  14. ^ Cite error: The named reference NRDD was invoked but never defined (see the help page).
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Memantine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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