4-Aminopyridine

4-Aminopyridine
Names
Preferred IUPAC name
Pyridin-4-amine
Other names
4-Pyridinamine
4-Pyridylamine
Para-aminopyridine
fampridine (INN)
dalfampridine (USAN)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.262 Edit this at Wikidata
EC Number
  • 207-987-9
KEGG
MeSH 4-Aminopyridine
UNII
  • InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) checkY
    Key: NUKYPUAOHBNCPY-UHFFFAOYSA-N checkY
  • InChI=1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
    Key: NUKYPUAOHBNCPY-UHFFFAOYAH
  • n1ccc(N)cc1
Properties
C5H6N2
Molar mass 94.1146 g/mol
Appearance colourless solid
Melting point 155 to 158 °C (311 to 316 °F; 428 to 431 K)
Boiling point 273 °C (523 °F; 546 K)
polar organic solvents
Basicity (pKb) 4.83[1]
Pharmacology
N07XX07 (WHO)
Oral
Pharmacokinetics:
96%
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
4-Aminopyridine

4-Aminopyridine (4-AP, fampridine, dalfampridine) is an organic compound with the chemical formula C5H4N–NH2. The molecule is one of the three isomeric amines of pyridine. It is used as a research tool in characterizing subtypes of the potassium channel. It has also been used as a drug, to manage some of the symptoms of multiple sclerosis,[7][8] and is indicated for symptomatic improvement of walking in adults with several variations of the disease.[9] It was undergoing Phase III clinical trials as of 2008,[10] and the U.S. Food and Drug Administration (FDA) approved the compound on January 22, 2010.[11] Fampridine is also marketed as Ampyra (pronounced "am-PEER-ah," according to the maker's website) in the United States by Acorda Therapeutics[11][12] and as Fampyra in the European Union, Canada, and Australia. In Canada, the medication has been approved for use by Health Canada since February 10, 2012.[13]


  1. ^ Albert A, Goldacre R, Phillips J (1948). "455. The strength of heterocyclic bases". Journal of the Chemical Society (Resumed): 2240–2249. doi:10.1039/JR9480002240.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Fampyra 10 mg prolonged-release tablets - Summary of Product Characteristics (SmPC)". (emc). 15 August 2018. Retrieved 24 August 2020.
  4. ^ "Ampyra- dalfampridine tablet, film coated, extended release". DailyMed. 20 December 2019. Retrieved 24 August 2020.
  5. ^ Cite error: The named reference Fampyra EPAR was invoked but never defined (see the help page).
  6. ^ "Dalfampridine (Ampyra) Use During Pregnancy". Drugs.com. 22 June 2020. Retrieved 24 August 2020.
  7. ^ Solari A, Uitdehaag B, Giuliani G, Pucci E, Taus C (2002). Solari A (ed.). "Aminopyridines for symptomatic treatment in multiple sclerosis". The Cochrane Database of Systematic Reviews (4): CD001330. doi:10.1002/14651858.CD001330. PMC 7047571. PMID 12804404.
  8. ^ Korenke AR, Rivey MP, Allington DR (October 2008). "Sustained-release fampridine for symptomatic treatment of multiple sclerosis". The Annals of Pharmacotherapy. 42 (10): 1458–1465. doi:10.1345/aph.1L028. PMID 18780812. S2CID 207263182.
  9. ^ "New Drugs: Fampridine". Australian Prescriber (34): 119–123. August 2011. Archived from the original on 2012-02-27.
  10. ^ "Acorda Clinical Development and Product Pipeline". Acorda.
  11. ^ a b "FDA Approves Ampyra to Improve Walking in Adults with Multiple Sclerosis". U.S. Food and Drug Administration (FDA) (Press release). Archived from the original on Jan 12, 2017.
  12. ^ "Ampyra". National Multiple Sclerosis Society.
  13. ^ "Notice of Decision for FAMPYRA". hc-sc.gc.ca. Archived from the original on 2012-05-02. Retrieved 2012-04-21.