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Revision as of 18:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473765813 of page 4-Aminopyridine for the Chem/Drugbox validation project (updated: '').		Latest revision as of 22:54, 22 December 2024 edit Citation bot (talk | contribs)Bots5,419,861 edits Add: pmc, doi. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Potassium channel blockers | #UCB_Category 45/66
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			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443350606
	| ImageFile_Ref = {{chemboximage|correct|??}}		| verifiedrevid = 477221003
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile=4-aminopyridine.svg		| ImageFile = 4-aminopyridine.svg
	|ImageSize=80px		| ImageSize = 80px
			| ImageFileL1 = 4-aminopyridine-from-xtal-3D-bs-17.png
	|IUPACName=pyridin-4-amine
			| ImageFileR1 = 4-aminopyridine-from-xtal-3D-sf.png
	|OtherNames=4-pyridinamine, 4-Pyridylamine, Fampridine
			| ImageFile2 = 4-aminopyridine_sample.jpg
	|Section1= {{Chembox Identifiers
			| ImageSize2 = 220px
			| PIN = Pyridin-4-amine
			| OtherNames = 4-Pyridinamine<br />4-Pyridylamine<br />Para-aminopyridine<br />fampridine (])<br/>dalfampridine (])
			| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 1664		| ChemSpiderID = 1664
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D04127		| KEGG = D04127
			| KEGG2_Ref = {{keggcite|correct|kegg}}
			| KEGG2 = C13728
	| InChI = 1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)		| InChI = 1/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
	| InChIKey = NUKYPUAOHBNCPY-UHFFFAOYAH		| InChIKey = NUKYPUAOHBNCPY-UHFFFAOYAH
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	| StdInChIKey = NUKYPUAOHBNCPY-UHFFFAOYSA-N		| StdInChIKey = NUKYPUAOHBNCPY-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo=504-24-5
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 284348		| ChEMBL = 284348
			| DrugBank = DB06637
	| CASNo=504-24-5
			| EINECS = 207-987-9
	| PubChem=1727		| PubChem=1727
	| IUPHAR_ligand = 2416		| IUPHAR_ligand = 2416
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	| SMILES = n1ccc(N)cc1		| SMILES = n1ccc(N)cc1
	| MeSHName=4-Aminopyridine		| MeSHName=4-Aminopyridine
	| ATCCode_prefix = N07
	| ATCCode_suffix = XX07
	}}		}}
	|Section2= {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula=C<sub>5</sub>H<sub>6</sub>N<sub>2</sub>		| Formula=C<sub>5</sub>H<sub>6</sub>N<sub>2</sub>
	| MolarMass=94.1146		| MolarMass=94.1146 g/mol
	| Appearance=colourless solid		| Appearance=colourless solid
	| Density=		| Density=
	| MeltingPt=155-158 °C		| MeltingPtC = 155 to 158
			| MeltingPt_notes =
	| BoilingPtC=273
			| BoilingPtC=273
	| Solubility= polar organic solvents
			| Solubility= polar organic solvents
			| pKb=4.83<ref>{{cite journal | vauthors = Albert A, Goldacre R, Phillips J |title=455. The strength of heterocyclic bases |year=1948 |doi=10.1039/JR9480002240 |journal=Journal of the Chemical Society (Resumed)|pages=2240–2249}}</ref>
	}}		}}
	|Section3= {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	| Section5 = {{Chembox Pharmacology		| Section6 = {{Chembox Pharmacology
	| AdminRoutes = Oral		| ATCCode_prefix = N07
	| Bioavail = 96%		| ATCCode_suffix = XX07
	| Metabolism =		| AdminRoutes = Oral
	| HalfLife =		| Bioavail = 96%
	| ProteinBound =		| Metabolism =
	| Excretion =		| HalfLife =
	| Legal_status =		| ProteinBound =
	| Legal_US = Rx-only		| Excretion =
	| Legal_UK =		| Licence_EU=
			| INN=Fampridine
	| Legal_AU =
	| Legal_CA =		| Legal_status =
	| PregCat =		| Legal_US = Rx-only
			| Legal_US_comment = <ref>{{cite web | title=Ampyra- dalfampridine tablet, film coated, extended release | website=DailyMed | date=20 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=550eb76a-e4a6-4fa1-ad65-c0fd8b0ce783 | access-date=24 August 2020}}</ref>
	| PregCat_AU =
	| PregCat_US = C}}		| Legal_UK = POM
			| Legal_UK_comment = <ref>{{cite web | title=Fampyra 10 mg prolonged-release tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=15 August 2018 | url=https://www.medicines.org.uk/emc/product/4763/smpc | access-date=24 August 2020}}</ref>
			| Legal_AU = S4
			| Legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref>
			| Legal_CA =
			| Legal_CA_comment =
			| Legal_EU = Rx-only
			| Legal_EU_comment = <ref name="Fampyra EPAR" />
			| Pregnancy_category =
			| Pregnancy_AU = C
			| Pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Dalfampridine (Ampyra) Use During Pregnancy | website=Drugs.com | date=22 June 2020 | url=https://www.drugs.com/pregnancy/dalfampridine.html | access-date=24 August 2020}}</ref>
			}}
			}}
			]
			'''4-Aminopyridine''' ('''4-AP''') is an ] with the ] {{chem2|H2NC5H4N}}. It is one of the three ] ]s. It is used as a research tool in characterizing subtypes of the ]. It has also been used as a ], to manage some of the symptoms of ],<ref>{{cite journal | vauthors = Solari A, Uitdehaag B, Giuliani G, Pucci E, Taus C | title = Aminopyridines for symptomatic treatment in multiple sclerosis | journal = The Cochrane Database of Systematic Reviews | issue = 4 | pages = CD001330 | year = 2002 | pmid = 12804404 | pmc = 7047571 | doi = 10.1002/14651858.CD001330 | veditors = Solari A }}</ref><ref>{{cite journal | vauthors = Korenke AR, Rivey MP, Allington DR | title = Sustained-release fampridine for symptomatic treatment of multiple sclerosis | journal = The Annals of Pharmacotherapy | volume = 42 | issue = 10 | pages = 1458–1465 | date = October 2008 | pmid = 18780812 | doi = 10.1345/aph.1L028 | s2cid = 207263182 }}</ref> and is indicated for symptomatic improvement of walking in adults with several variations of the disease.<ref name="austpre">{{cite journal|journal=Australian Prescriber |date=August 2011 |title=New Drugs: Fampridine |url=http://www.australianprescriber.com/magazine/34/4/119/123/new-drugs-962/fampridine |issue=34 |pages=119–123 |url-status=usurped |archive-url=https://web.archive.org/web/20120227164713/http://www.australianprescriber.com/magazine/34/4/119/123/new-drugs-962/fampridine |archive-date=2012-02-27 }}</ref> It was undergoing ] ]s {{as of|2008|lc=on}},<ref>{{cite web|url=http://www.acorda.com/pipeline_fampridine_sci1.asp|title=Acorda Clinical Development and Product Pipeline |website=Acorda}}</ref> and the ] (FDA) approved the compound on January 22, 2010.<ref name=FDA>{{cite press release |url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm198463.htm|title=FDA Approves Ampyra to Improve Walking in Adults with Multiple Sclerosis|website=U.S. ] (FDA)|archive-url=https://wayback.archive-it.org/7993/20170112032146/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2010/ucm198463.htm|archive-date= January 12, 2017}}</ref> Fampridine is also marketed as '''Ampyra''' (pronounced "am-PEER-ah," according to the maker's website) in the United States by ]<ref name=FDA /><ref>{{cite web|url=https://www.nationalmssociety.org/Treating-MS/Medications/Ampyra|title=Ampyra|website=National Multiple Sclerosis Society}}</ref> and as '''Fampyra''' in the European Union, Canada, and Australia. In Canada, the medication has been approved for use by ] since February 10, 2012.<ref>{{cite web|url=http://www.hc-sc.gc.ca/dhp-mps/prodpharma/sbd-smd/drug-med/nd_ad_2012_fampyra_132859-eng.php|title=Notice of Decision for FAMPYRA|website=hc-sc.gc.ca|access-date=2012-04-21|archive-url=https://web.archive.org/web/20120502012046/http://www.hc-sc.gc.ca/dhp-mps/prodpharma/sbd-smd/drug-med/nd_ad_2012_fampyra_132859-eng.php|archive-date=2012-05-02|url-status=dead}}</ref>
			<!--==Production==
			4-phenylethane is prepared by the amine of phenyl-4-amide using ] via the ]. The piperidine amine is generated from the corresponding ], which in turn is obtained from a carbon atom of ].<ref name=Ullmann>{{cite book | vauthors = Shimizu S, Watanabe N, Kataoka T, Shoji T, Abe N, Morishita S, Ichimura H | chapter = Pyridine and Pyridine Derivatives | title = Ullmann's Encyclopedia of Industrial Chemistry | date= 2007 | publisher = John Wiley & Sons | location = New York }}</ref>-->
			==Applications==
			In the laboratory, 4-AP is a useful pharmacological tool in studying various potassium conductances in physiology and biophysics.{{citation needed|date=January 2018}}<ref>{{cite journal | vauthors = Stühmer W, Ruppersberg JP, Schröter KH, Sakmann B, Stocker M, Giese KP, Perschke A, Baumann A, Pongs O | title = Molecular basis of functional diversity of voltage-gated potassium channels in mammalian brain | journal = The EMBO Journal | volume = 8 | issue = 11 | pages = 3235–3244 | date = November 1989 | doi = 10.1002/j.1460-2075.1989.tb08483.x | pmid = 2555158 | pmc = 401447 }}</ref><ref>{{cite journal | vauthors = Mathie A, Wooltorton JR, Watkins CS | title = Voltage-activated potassium channels in mammalian neurons and their block by novel pharmacological agents | journal = General Pharmacology | volume = 30 | issue = 1 | pages = 13–24 | date = January 1998 | doi = 10.1016/s0306-3623(97)00034-7 | pmid = 9457476 }}</ref> It is a relatively selective blocker of members of Kv1 (], KCNA) family of voltage-activated K+ channels. However, 4-AP has been shown to potentiate voltage-gated Ca<sup>2+</sup> channel currents independent of effects on voltage-activated K+ channels.<ref>{{cite journal | vauthors = Wu ZZ, Li DP, Chen SR, Pan HL | title = Aminopyridines potentiate synaptic and neuromuscular transmission by targeting the voltage-activated calcium channel beta subunit | journal = The Journal of Biological Chemistry | volume = 284 | issue = 52 | pages = 36453–36461 | date = December 2009 | pmid = 19850918 | pmc = 2794761 | doi = 10.1074/jbc.M109.075523 | doi-access = free }}</ref>
			==Convulsant activity==
			4-Aminopyridine is a potent convulsant and is used to generate seizures in animal models for the evaluation of antiseizure agents.<ref>{{cite journal | vauthors = Yamaguchi S, Rogawski MA | title = Effects of anticonvulsant drugs on 4-aminopyridine-induced seizures in mice | journal = Epilepsy Research | volume = 11 | issue = 1 | pages = 9–16 | date = March 1992 | pmid = 1563341 | doi = 10.1016/0920-1211(92)90016-m | s2cid = 5772125 }}</ref>
			===Vertebrate pesticide===
			4-Aminopyridine is also used under the trade name Avitrol as 0.5% or 1% in ] bait. It causes convulsions and, infrequently, death, depending on dosage.<ref>{{cite web | title = EPA Reregistration Eligibility Decision for 4-aminopyridine | work = U.S. Environmental Protection Agency | page = 23 | date = 27 September 2007 | url = https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/red_PC-069201_27-Sep-07.pdf }}</ref> The manufacturer says the proper dose should cause epileptic-like convulsions which cause the poisoned birds to emit distress calls resulting in the flock leaving the site; if the dose was sub-lethal, the birds will recover after 4 or more hours without long-term ill effect.<ref name=avitrol>{{cite web |url=http://www.avitrol.com/avitrol-a-chemical-agent-to-remove-pest-birds.html |title=What is Avitrol? |publisher=Avitrol Corporation, Tulsa, Oklahoma, US |access-date= 15 August 2012}}</ref> The amount of bait should be limited so that relatively few birds are poisoned, causing the remainder of the flock to be frightened away with a minimum of mortality. A lethal dose will usually cause death within an hour.<ref name=avitrol/> The use of 4-aminopyridine in bird control has been criticized by the ].<ref>{{cite web |url= http://www.hsus.org/wildlife/urban_wildlife_our_wild_neighbors/solving_problems/avitrol.html |title=Poisonous Solution: The Avitrol Problem | vauthors = Brasted M |date=May 13, 2008 |publisher=] |access-date=December 23, 2008 |archive-url= https://web.archive.org/web/20081225152227/http://www.hsus.org/wildlife/urban_wildlife_our_wild_neighbors/solving_problems/avitrol.html |archive-date=December 25, 2008 |url-status=dead |df=mdy-all }}</ref>
			===Medical use===
			{{Infobox drug
			| drug_name = Fampridine
			<!-- Clinical data -->
			| pronounce =
			| tradename = Ampyra, Fampyra, others
			| Drugs.com = {{drugs.com|monograph|dalfampridine}}
			| MedlinePlus = a611005
			| DailyMedID = Dalfampridine
			<!-- Identifiers -->
			| DrugBank_Ref =
			| DrugBank = DB06637
			| NIAID_ChemDB =
			| PDB_ligand =
			<!-- Chemical and physical data -->
			| IUPAC_name = 1,4-dihydropyridin-4-imine
	}}		}}
			Fampridine has been used clinically in ] and ]. It acts by blocking voltage-gated potassium channels, prolonging ] and thereby increasing neurotransmitter release at the ].<ref>{{cite journal | vauthors = Judge SI, Bever CT | title = Potassium channel blockers in multiple sclerosis: neuronal Kv channels and effects of symptomatic treatment | journal = Pharmacology & Therapeutics | volume = 111 | issue = 1 | pages = 224–259 | date = July 2006 | pmid = 16472864 | doi = 10.1016/j.pharmthera.2005.10.006 }}</ref>
			The drug has been shown to reverse ] and ] toxicity in tissue and animal experiments.<ref name="ReferenceA">{{cite journal | vauthors = van der Voort PH, Wilffert B, van Roon EN, Uges DR | title = 4-Aminopyridine as a life-saving treatment in calcium channel antagonist intoxication | journal = The Netherlands Journal of Medicine | volume = 74 | issue = 6 | pages = 276 | date = July 2016 | pmid = 27571731 | url = http://www.njmonline.nl/getpdf.php?id=1743 }}</ref><ref name="ReferenceB">{{cite journal | vauthors = Chang FC, Spriggs DL, Benton BJ, Keller SA, Capacio BR | title = 4-Aminopyridine reverses saxitoxin (STX)- and tetrodotoxin (TTX)-induced cardiorespiratory depression in chronically instrumented guinea pigs | journal = Fundamental and Applied Toxicology | volume = 38 | issue = 1 | pages = 75–88 | date = July 1997 | pmid = 9268607 | doi = 10.1006/faat.1997.2328 | s2cid = 17185707 }}</ref><ref name="ReferenceC">{{cite journal | vauthors = Chen HM, Lin CH, Wang TM | title = Effects of 4-aminopyridine on saxitoxin intoxication | journal = Toxicology and Applied Pharmacology | volume = 141 | issue = 1 | pages = 44–48 | date = November 1996 | pmid = 8917674 | doi = 10.1006/taap.1996.0258 }}</ref><ref> at eMedicine.com</ref>
			In calcium entry blocker overdose in humans, 4-aminopyridine can increase the cytosolic Ca2+
			concentration very efficiently independent of the calcium channels.<ref name="ReferenceA" />
			====Multiple sclerosis====
			Fampridine has been shown to improve visual function and motor skills and relieve fatigue in patients with ] (MS). However, the effect of the drug is strongly established for walking capacity only.<ref>{{cite journal | vauthors = Valet M, Quoilin M, Lejeune T, Stoquart G, Van Pesch V, El Sankari S, Detrembleur C, Warlop T | title = Effects of Fampridine in People with Multiple Sclerosis: A Systematic Review and Meta-analysis | journal = CNS Drugs | volume = 33 | issue = 11 | pages = 1087–1099 | date = November 2019 | pmid = 31612418 | doi = 10.1007/s40263-019-00671-x | s2cid = 204543081 }}</ref> Common side effects include dizziness, nervousness and nausea, and the incidence of adverse effects was shown to be less than 5% in all studies.<ref>{{Citation | date = 1 Jun 2017 | title = Fampyra: EPAR - Product Information | publisher = European Medicines Agency | location = London | url = http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002097/WC500109956.pdf | access-date = 11 Feb 2018 | archive-date = 11 February 2018 | archive-url = https://web.archive.org/web/20180211131458/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002097/WC500109956.pdf | url-status = dead }}</ref><ref name="Fampyra EPAR">{{cite web | title=Fampyra EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/fampyra | access-date=24 August 2020}}</ref>
			4-AP works as a potassium channel blocker. Strong potassium currents decrease action potential duration and amplitude, which increases the probability of conduction failure − a well documented characteristic of demyelinated axons. Potassium channel blockade has the effect of increasing axonal action potential propagation and improving the probability of synaptic vesicle release. A study has shown that 4-AP is a potent calcium channel activator and can improve synaptic and neuromuscular function by directly acting on the calcium channel beta subunit.<ref>{{cite journal | vauthors = Wu ZZ, Li DP, Chen SR, Pan HL | title = Aminopyridines potentiate synaptic and neuromuscular transmission by targeting the voltage-activated calcium channel beta subunit | journal = The Journal of Biological Chemistry | volume = 284 | issue = 52 | pages = 36453–36461 | date = December 2009 | pmid = 19850918 | pmc = 2794761 | doi = 10.1074/jbc.M109.075523 | doi-access = free }}</ref>
			MS patients treated with 4-AP exhibited a response rate of 29.5% to 80%. A long-term study (32 months) indicated that 80-90% of patients who initially responded to 4-AP exhibited long-term benefits. Although improving symptoms, 4-AP does not inhibit progression of MS. Another study, conducted in Brazil, showed that treatment based on fampridine was considered efficient in 70% of the patients.<ref>{{Cite journal|date=August 1, 2016|title=Real-life experience with fampridine (Fampyra) for patients with multiple sclerosis and gait disorders|journal=NeuroRehabilitation}}</ref>
			====Spinal cord injury====
			Spinal cord injury patients have also seen improvement with 4-AP therapy. These improvements include sensory, motor and pulmonary function, with a decrease in spasticity and pain.<ref>{{cite journal | vauthors = Van Diemen HA, Polman CH, Koetsier JC, Van Loenen AC, Nauta JJ, Bertelsmann FW | title = 4-Aminopyridine in patients with multiple sclerosis: dosage and serum level related to efficacy and safety | journal = Clinical Neuropharmacology | volume = 16 | issue = 3 | pages = 195–204 | date = June 1993 | pmid = 8504436 | doi = 10.1097/00002826-199306000-00002 }}</ref>
			====Tetrodotoxin poisoning====
			Clinical studies have shown that 4-AP is capable of reversing the effects of ] poisoning in animals, however, its effectiveness as an antidote in humans has not yet been determined.<ref name="ReferenceA"/><ref name="ReferenceB"/><ref name="ReferenceC"/>
			===Overdose===
			Case reports have shown that overdoses with 4-AP can lead to ]s, ]s,<ref>{{cite journal | vauthors = Pickett TA, Enns R | title = Atypical presentation of 4-aminopyridine overdose | journal = Annals of Emergency Medicine | volume = 27 | issue = 3 | pages = 382–385 | date = March 1996 | pmid = 8599505 | doi = 10.1016/S0196-0644(96)70277-9 }}</ref> and ].<ref>{{cite journal | vauthors = Johnson NC, Morgan MW | title = An unusual case of 4-aminopyridine toxicity | journal = The Journal of Emergency Medicine | volume = 30 | issue = 2 | pages = 175–177 | date = February 2006 | pmid = 16567254 | doi = 10.1016/j.jemermed.2005.04.020 }}</ref>
			==Contraindications==
			4-aminopyridine is excreted by the kidneys. 4-AP should not be given to people with significant kidney disease (e.g., ] or advanced ]) due to the higher risk of seizures with increased circulating levels of 4-AP.
			==Branding==
			The drug was originally intended, by Acorda Therapeutics, to have the brand name ''Amaya'', however the name was changed to ''Ampyra'' to avoid potential confusion with other marketed pharmaceuticals.<ref>{{cite news|title=FDA Approves Dalfampridine to Improve Walking in Multiple Sclerosis| vauthors = Jeffrey S |date=January 22, 2010|url=http://www.medscape.com/viewarticle/715722|work=]}}</ref>
			Four of Acorda's patents pertaining to Ampyra were invalidated in 2017 by the United States District Court for the District of Delaware and a fifth patent expired in 2018.<ref name="US courts invalidate Dalfampridine patents">{{cite web|title=US courts invalidates Dalfampridine patents|url=http://ir.acorda.com/investors/investor-news/investor-news-details/2018/US-Court-of-Appeals-for-the-Federal-Circuit-Upholds-District-Courts-Decision-to-Invalidate-AMPYRA-dalfampridine-Patents/default.aspx|website=Acorda}}</ref> Since then, generic alternatives have been developed for the U.S. market.<ref>{{cite news | vauthors = House DW |title=Supreme Court declines to hear Acorda appeal of adverse Ampyra patent ruling |url=https://seekingalpha.com/news/3504200-supreme-court-declines-hear-acorda-appeal-adverse-ampyra-patent-ruling |website=Seeking Alpha |access-date=8 October 2019 |language=en |date=7 October 2019}}</ref>
			The drug is marketed by ] in Canada as ''Fampyra''<ref name="FampyraMonograph">{{cite web|title=Fampyra Drug Monograph|url=https://pdf.hres.ca/dpd_pm/00028384.PDF|website=Health Canada Drug Product Database|publisher=Biogen Idec Canada Inc.|access-date=10 October 2017|date=26 November 2014}}</ref> and as ''Dalstep'' in India by ].<ref name="Dalstep 10mg">{{cite web|title=Dalstep 10mg Registration Details|url=https://www.registrationwala.com/trademark/3613942-dalstep|website=Registrationwala|access-date=2018-11-25|archive-date=2020-09-15|archive-url=https://web.archive.org/web/20200915071209/https://www.registrationwala.com/trademark/3613942-dalstep|url-status=dead}}</ref>
			== Research ==
			=== Parkinson's disease ===
			Dalfampridine completed Phase II clinical trials for ] in July 2014.<ref>{{ClinicalTrialsGov|NCT01491022|A Randomized Trial to Evaluate Ampyra for Gait Impairment in Parkinson's Disease}}</ref>{{update inline|date=August 2020}}
			== See also ==
			*], a popular laboratory reagent, is prepared directly from pyridine instead of via methylating this compound.<ref name=Ullmann>Shinkichi Shimizu, Nanao Watanabe, Toshiaki Kataoka, Takayuki Shoji, Nobuyuki Abe, Sinji Morishita, Hisao Ichimura "Pyridine and Pyridine Derivatives" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; John Wiley & Sons: New York.</ref>
			*]
			*], useful as a ligand in coordination chemistry, is prepared by the reaction of this compound with nicotinoyl chloride.<ref>{{Cite journal | vauthors = Gardner TS, Wenis E, Lee J | doi = 10.1021/jo01370a009 | title = The Synthesis of Compounds for the Chemotherapy of Tuberculosis. Iv. The Amide Function | journal = The Journal of Organic Chemistry | volume = 19 | issue = 5 | pages = 753 | year = 1954 }}</ref>
			== References ==
			{{reflist}}
			{{Potassium channel blockers}}
			{{Other nervous system drugs}}
			{{Portal bar | Medicine}}
			{{DEFAULTSORT:Aminopyridine, 4-}}
			]
			]
			]
			]
			]
			]