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, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. It was undergoing Phase III clinical trials as of 2008, and the U.S. Food and Drug Administration (FDA) approved the compound on January 22, 2010. Fampridine is also marketed as Ampyra (pronounced "am-PEER-ah," according to the maker's website) in the United States by Acorda Therapeutics 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.

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
EC Number
  • 207-987-9
KEGG
MeSH 4-Aminopyridine
PubChem CID
UNII
  • InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) Y
    Key: NUKYPUAOHBNCPY-UHFFFAOYSA-N Y
  • InChI=1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
    Key: NUKYPUAOHBNCPY-UHFFFAOYAH
SMILES
  • 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
Pharmacology
N07XX07 (WHO)
Pregnancy
category
  • AU: C
Routes of
administration
 Oral
Pharmacokinetics:
96%
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references


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