fampridine   Click here for help

GtoPdb Ligand ID: 2416

Synonyms: 4-aminopyridine | 4-AP | Ampyra® | EL-970
Approved drug
fampridine is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: Fampridine is the INN for this compound, whereas its USAN is dalfampridine.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 38.91
Molecular weight 94.05
XLogP -0.05
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES Nc1ccncc1
Isomeric SMILES Nc1ccncc1
InChI InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
1. Fedida D, Wible B, Wang Z, Fermini B, Faust F, Nattel S, Brown AM. (1993)
Identity of a novel delayed rectifier current from human heart with a cloned K+ channel current.
Circ Res, 73 (1): 210-6. [PMID:8508531]
2. Finol-Urdaneta RK, Strüver N, Terlau H. (2006)
Molecular and Functional Differences between Heart mKv1.7 Channel Isoforms.
J Gen Physiol, 128 (1): 133-45. [PMID:16801386]
3. Gordon E, Cohen JL, Engel R, Abbott GW. (2006)
1,4-Diazabicyclo[2.2.2]octane derivatives: a novel class of voltage-gated potassium channel blockers.
Mol Pharmacol, 69 (3): 718-26. [PMID:16317109]
4. Grissmer S, Nguyen AN, Aiyar J, Hanson DC, Mather RJ, Gutman GA, Karmilowicz MJ, Auperin DD, Chandy KG. (1994)
Pharmacological characterization of five cloned voltage-gated K+ channels, types Kv1.1, 1.2, 1.3, 1.5, and 3.1, stably expressed in mammalian cell lines.
Mol Pharmacol, 45 (6): 1227-34. [PMID:7517498]
5. Holmqvist MH, Cao J, Hernandez-Pineda R, Jacobson MD, Carroll KI, Sung MA, Betty M, Ge P, Gilbride KJ, Brown ME et al.. (2002)
Elimination of fast inactivation in Kv4 A-type potassium channels by an auxiliary subunit domain.
Proc Natl Acad Sci USA, 99 (2): 1035-40. [PMID:11805342]
6. Isbrandt D, Leicher T, Waldschütz R, Zhu X, Luhmann U, Michel U, Sauter K, Pongs O. (2000)
Gene structures and expression profiles of three human KCND (Kv4) potassium channels mediating A-type currents I(TO) and I(SA).
Genomics, 64 (2): 144-54. [PMID:10729221]
7. Juvin V, Penna A, Chemin J, Lin YL, Rassendren FA. (2007)
Pharmacological characterization and molecular determinants of the activation of transient receptor potential V2 channel orthologs by 2-aminoethoxydiphenyl borate.
Mol Pharmacol, 72 (5): 1258-68. [PMID:17673572]
8. Kalman K, Nguyen A, Tseng-Crank J, Dukes ID, Chandy G, Hustad CM, Copeland NG, Jenkins NA, Mohrenweiser H, Brandriff B et al.. (1998)
Genomic organization, chromosomal localization, tissue distribution, and biophysical characterization of a novel mammalian Shaker-related voltage-gated potassium channel, Kv1.7.
J Biol Chem, 273 (10): 5851-7. [PMID:9488722]
9. Kirsch GE, Drewe JA. (1993)
Gating-dependent mechanism of 4-aminopyridine block in two related potassium channels.
J Gen Physiol, 102 (5): 797-816. [PMID:8301258]
10. Korenke AR, Rivey MP, Allington DR. (2008)
Sustained-release fampridine for symptomatic treatment of multiple sclerosis.
Ann Pharmacother, 42 (10): 1458-65. [PMID:18780812]
11. Krapivinsky G, Medina I, Eng L, Krapivinsky L, Yang Y, Clapham DE. (1998)
A novel inward rectifier K+ channel with unique pore properties.
Neuron, 20 (5): 995-1005. [PMID:9620703]
12. Lang R, Lee G, Liu W, Tian S, Rafi H, Orias M, Segal AS, Desir GV. (2000)
KCNA10: a novel ion channel functionally related to both voltage-gated potassium and CNG cation channels.
Am J Physiol Renal Physiol, 278 (6): F1013-21. [PMID:10836990]
13. Lien CC, Martina M, Schultz JH, Ehmke H, Jonas P. (2002)
Gating, modulation and subunit composition of voltage-gated K(+) channels in dendritic inhibitory interneurones of rat hippocampus.
J Physiol (Lond.), 538 (Pt 2): 405-19. [PMID:11790809]
14. Schmalz F, Kinsella J, Koh SD, Vogalis F, Schneider A, Flynn ER, Kenyon JL, Horowitz B. (1998)
Molecular identification of a component of delayed rectifier current in gastrointestinal smooth muscles.
Am J Physiol, 274 (5 Pt 1): G901-11. [PMID:9612272]
15. Solari A, Uitdehaag B, Giuliani G, Pucci E, Taus C. (2001)
Aminopyridines for symptomatic treatment in multiple sclerosis.
Cochrane Database Syst Rev, (4): CD001330. [PMID:11687106]
16. Stühmer W, Ruppersberg JP, Schröter KH, Sakmann B, Stocker M, Giese KP, Perschke A, Baumann A, Pongs O. (1989)
Molecular basis of functional diversity of voltage-gated potassium channels in mammalian brain.
EMBO J, 8 (11): 3235-44. [PMID:2555158]
17. Vega-Saenz de Miera E, Moreno H, Fruhling D, Kentros C, Rudy B. (1992)
Cloning of ShIII (Shaw-like) cDNAs encoding a novel high-voltage-activating, TEA-sensitive, type-A K+ channel.
Proc Biol Sci, 248 (1321): 9-18. [PMID:1381835]
18. Yeung SY, Ohya S, Sergeant GP, Pucovský V, Greenwood IA. (2006)
Pharmacological and molecular evidence for the involvement of Kv4.3 in ultra-fast activating K+ currents in murine portal vein myocytes.
Br J Pharmacol, 149 (6): 676-86. [PMID:17016508]