3,4-Diaminopyridine
(from PubChem) Amifampridine, or 3,4-diaminopyridine (3,4-DAP), is a quaternary ammonium compound that blocks presynaptic potassium channels, and subsequently prolongs the action potential and increases presynaptic calcium concentrations. It was first discovered in Scotland in the 1970s and its clinical effectiveness for neuromuscular disorders, including Lambert-Eaton myasthenic syndrome (LEMS), has been investigated in the 1980s Patients with LEMS develop serum antibodies against presynaptic P\/Q-type voltage-gated calcium channels, leading to decreased presynaptic calcium levels and reduced quantal release of acetylcholine. Used for treatment Botulinum neurotoxin: nature's deadliest biomolecule.
General
Type : Pyridine, Calcium Channel Antagonist
Chemical_Nomenclature :
Canonical SMILES :
InChI :
InChIKey :
Other name(s) : pyridine-3,4-diamine || Amifampridine || Firdapse || 3,4-Pyridinediamine || 3,4-DAP || CHEMBL354077 || SCHEMBL21273 || CHEBI:135948 || ZINC164000
Target
Families : No family
Protein : No protein
References (38)
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| Author(s) : Lee M , Beeson D , Palace J |
| Ref : Annals of the New York Academy of Sciences , 1412 :129 , 2018 |
| Abstract : |
| PubMedSearch : Lee_2018_Ann.N.Y.Acad.Sci_1412_129 |
| PubMedID: 29381222 |
| Title : 3,4-Diaminopyridine may improve myasthenia gravis with MuSK antibodies - |
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| Ref : Neurology , 86 :1070 , 2016 |
| PubMedID: 26873957 |
| Title : Genetic variation in aryl N-acetyltransferase results in significant differences in the pharmacokinetic and safety profiles of amifampridine (3,4-diaminopyridine) phosphate - Haroldsen_2015_Pharmacol.Res.Perspect_3_e00099 |
| Author(s) : Haroldsen PE , Garovoy MR , Musson DG , Zhou H , Tsuruda L , Hanson B , O'Neill CA |
| Ref : Pharmacol Res Perspect , 3 :e00099 , 2015 |
| Abstract : |
| PubMedSearch : Haroldsen_2015_Pharmacol.Res.Perspect_3_e00099 |
| PubMedID: 25692017 |
| Title : The Facilitatory Effect of Casearia sylvestris Sw. (guacatonga) Fractions on the Contractile Activity of Mammalian and Avian Neuromuscular Apparatus - Werner_2015_Curr.Pharm.Biotechnol_16_468 |
| Author(s) : Werner AC , Ferraz MC , Yoshida EH , Tribuiani N , Gautuz JA , Santana MN , Dezzotti BA , de Miranda VG , Foramiglio AL , Rostelato-Ferreira S , Tavares RV , Hyslop S , Oshima-Franco Y |
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| Abstract : |
| PubMedSearch : Werner_2015_Curr.Pharm.Biotechnol_16_468 |
| PubMedID: 25751174 |
| Title : The European LEMS Registry: Baseline Demographics and Treatment Approaches - Mantegazza_2015_Neurol.Ther_4_105 |
| Author(s) : Mantegazza R , Meisel A , Sieb JP , Le Masson G , Desnuelle C , Essing M |
| Ref : Neurol Ther , 4 :105 , 2015 |
| Abstract : |
| PubMedSearch : Mantegazza_2015_Neurol.Ther_4_105 |
| PubMedID: 26525537 |
| Title : Presynaptic Disorders: Lambert-Eaton Myasthenic Syndrome and Botulism - Gable_2015_Semin.Neurol_35_340 |
| Author(s) : Gable KL , Massey JM |
| Ref : Semin Neurol , 35 :340 , 2015 |
| Abstract : |
| PubMedSearch : Gable_2015_Semin.Neurol_35_340 |
| PubMedID: 26502758 |
| Title : Pharmacologic treatment of downstream of tyrosine kinase 7 congenital myasthenic syndrome - Witting_2014_JAMA.Neurol_71_350 |
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| Ref : JAMA Neurol , 71 :350 , 2014 |
| Abstract : |
| PubMedSearch : Witting_2014_JAMA.Neurol_71_350 |
| PubMedID: 24425145 |
| Title : 3,4-Diaminopyridine may improve neuromuscular block during botulism - |
| Author(s) : Friggeri A , Marcon F , Marciniak S , Lemaire-Hurtel AS , Seydi A , Ammenouche N , Levrard M , Mahjoub Y , Airapetian N , Tinturier F , Petitjean M , Dupont H |
| Ref : Crit Care , 17 :449 , 2013 |
| PubMedID: 24007658 |
| Title : Pyridostigmine but not 3,4-diaminopyridine exacerbates ACh receptor loss and myasthenia induced in mice by muscle-specific kinase autoantibody - Morsch_2013_J.Physiol_591_2747 |
| Author(s) : Morsch M , Reddel SW , Ghazanfari N , Toyka KV , Phillips WD |
| Ref : The Journal of Physiology , 591 :2747 , 2013 |
| Abstract : |
| PubMedSearch : Morsch_2013_J.Physiol_591_2747 |
| PubMedID: 23440963 |
| Title : 3,4-Diaminopyridine improves neuromuscular transmission in a MuSK antibody-induced mouse model of myasthenia gravis - Mori_2012_J.Neuroimmunol_245_75 |
| Author(s) : Mori S , Kishi M , Kubo S , Akiyoshi T , Yamada S , Miyazaki T , Konishi T , Maruyama N , Shigemoto K |
| Ref : Journal of Neuroimmunology , 245 :75 , 2012 |
| Abstract : |
| PubMedSearch : Mori_2012_J.Neuroimmunol_245_75 |
| PubMedID: 22409941 |
| Title : Recurrent COLQ mutation in congenital myasthenic syndrome - Guven_2012_Pediatr.Neurol_46_253 |
| Author(s) : Guven A , Demirci M , Anlar B |
| Ref : Pediatr Neurol , 46 :253 , 2012 |
| Abstract : |
| PubMedSearch : Guven_2012_Pediatr.Neurol_46_253 |
| PubMedID: 22490774 |
| Title : Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization - Zakhari_2011_Bioorg.Med.Chem_19_6203 |
| Author(s) : Zakhari JS , Kinoyama I , Hixon MS , Di Mola A , Globisch D , Janda KD |
| Ref : Bioorganic & Medicinal Chemistry , 19 :6203 , 2011 |
| Abstract : |
| PubMedSearch : Zakhari_2011_Bioorg.Med.Chem_19_6203 |
| PubMedID: 21975066 |
| Title : Update on treatment options for Lambert-Eaton myasthenic syndrome: focus on use of amifampridine - Lindquist_2011_Neuropsychiatr.Dis.Treat_7_341 |
| Author(s) : Lindquist S , Stangel M |
| Ref : Neuropsychiatr Dis Treat , 7 :341 , 2011 |
| Abstract : |
| PubMedSearch : Lindquist_2011_Neuropsychiatr.Dis.Treat_7_341 |
| PubMedID: 21822385 |
| Title : Beneficial effect of albuterol in congenital myasthenic syndrome with epsilon-subunit mutations - Sadeh_2011_Muscle.Nerve_44_289 |
| Author(s) : Sadeh M , Shen XM , Engel AG |
| Ref : Muscle & Nerve , 44 :289 , 2011 |
| Abstract : |
| PubMedSearch : Sadeh_2011_Muscle.Nerve_44_289 |
| PubMedID: 21721016 |
| Title : The effect of 3,4-diaminopyridine on the patients with hereditary pure cerebellar ataxia - Tsunemi_2010_J.Neurol.Sci_292_81 |
| Author(s) : Tsunemi T , Ishikawa K , Tsukui K , Sumi T , Kitamura K , Mizusawa H |
| Ref : Journal of Neurology Sci , 292 :81 , 2010 |
| Abstract : |
| PubMedSearch : Tsunemi_2010_J.Neurol.Sci_292_81 |
| PubMedID: 20181362 |
| Title : 3,4-diaminopyridine for the treatment of Lambert-Eaton myasthenic syndrome - Wirtz_2010_Expert.Rev.Clin.Immunol_6_867 |
| Author(s) : Wirtz PW , Titulaer MJ , Gerven JM , Verschuuren JJ |
| Ref : Expert Rev Clin Immunol , 6 :867 , 2010 |
| Abstract : |
| PubMedSearch : Wirtz_2010_Expert.Rev.Clin.Immunol_6_867 |
| PubMedID: 20979551 |
| Title : [Treatment approach to congenital myasthenic syndrome in a patient with acetylcholine receptor deficiency] - Ishigaki_2009_No.To.Hattatsu_41_37 |
| Author(s) : Ishigaki K , Murakami T , Ito Y , Yanagisawa A , Kodaira K , Shishikura K , Suzuki H , Hirayama Y , Osawa M |
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| Abstract : |
| PubMedSearch : Ishigaki_2009_No.To.Hattatsu_41_37 |
| PubMedID: 19172815 |
| Title : Therapeutic strategies in congenital myasthenic syndromes - Schara_2008_Neurotherapeutics_5_542 |
| Author(s) : Schara U , Lochmuller H |
| Ref : Neurotherapeutics , 5 :542 , 2008 |
| Abstract : |
| PubMedSearch : Schara_2008_Neurotherapeutics_5_542 |
| PubMedID: 19019305 |
| Title : Novel truncating RAPSN mutations causing congenital myasthenic syndrome responsive to 3,4-diaminopyridine - Banwell_2004_Neuromuscul.Disord_14_202 |
| Author(s) : Banwell BL , Ohno K , Sieb JP , Engel AG |
| Ref : Neuromuscular Disorders , 14 :202 , 2004 |
| Abstract : |
| PubMedSearch : Banwell_2004_Neuromuscul.Disord_14_202 |
| PubMedID: 15036330 |
| Title : Improvement of dy\/dy dystrophic diaphragm by 3,4-diaminopyridine - van Lunteren_2002_Muscle.Nerve_26_71 |
| Author(s) : van Lunteren E , Moyer M |
| Ref : Muscle & Nerve , 26 :71 , 2002 |
| Abstract : |
| PubMedSearch : van Lunteren_2002_Muscle.Nerve_26_71 |
| PubMedID: 12115951 |
| Title : 3,4-Diaminopyridine, an orphan drug, in the symptomatic treatment of Lambert-Eaton myasthenic syndrome - Molgo_1996_Pflugers.Arch_431_R295 |
| Author(s) : Molgo J , Guglielmi JM |
| Ref : Pflugers Arch , 431 :R295 , 1996 |
| Abstract : |
| PubMedSearch : Molgo_1996_Pflugers.Arch_431_R295 |
| PubMedID: 8739381 |
| Title : Physostigmine, but not 3,4-diaminopyridine, improves radial maze performance in memory-impaired rats - Beninger_1995_Pharmacol.Biochem.Behav_51_739 |
| Author(s) : Beninger RJ , Wirsching BA , Mallet PE , Jhamandas K , Boegman RJ |
| Ref : Pharmacol Biochem Behav , 51 :739 , 1995 |
| Abstract : |
| PubMedSearch : Beninger_1995_Pharmacol.Biochem.Behav_51_739 |
| PubMedID: 7675853 |
| Title : Treatment of stable chronic demyelinating polyneuropathy with 3,4-diaminopyridine - Russell_1995_Mayo.Clin.Proc_70_532 |
| Author(s) : Russell JW , Windebank AJ , Harper CM, Jr. |
| Ref : Mayo Clin Proc , 70 :532 , 1995 |
| Abstract : |
| PubMedSearch : Russell_1995_Mayo.Clin.Proc_70_532 |
| PubMedID: 7776711 |
| Title : 3,4-Diaminopyridine and choline increase in vivo acetylcholine release in rat striatum - Buyukuysal_1995_Eur.J.Pharmacol_281_179 |
| Author(s) : Buyukuysal RL , Ulus IH , Aydin S , Kiran BK |
| Ref : European Journal of Pharmacology , 281 :179 , 1995 |
| Abstract : |
| PubMedSearch : Buyukuysal_1995_Eur.J.Pharmacol_281_179 |
| PubMedID: 7589205 |
| Title : 3,4-Diaminopyridine facilitates norepinephrine release in chick sympathetic neurons - Huang_1995_Zhongguo.Yao.Li.Xue.Bao_16_348 |
| Author(s) : Huang HY , Zhou CW |
| Ref : Zhongguo Yao Li Xue Bao , 16 :348 , 1995 |
| Abstract : |
| PubMedSearch : Huang_1995_Zhongguo.Yao.Li.Xue.Bao_16_348 |
| PubMedID: 7668108 |
| Title : 4-Aminopyridine is superior to 3,4-diaminopyridine in the treatment of patients with multiple sclerosis - Polman_1994_Arch.Neurol_51_1136 |
| Author(s) : Polman CH , Bertelsmann FW , de Waal R , van Diemen HA , Uitdehaag BM , van Loenen AC , Koetsier JC |
| Ref : Archives of Neurology , 51 :1136 , 1994 |
| Abstract : |
| PubMedSearch : Polman_1994_Arch.Neurol_51_1136 |
| PubMedID: 7980110 |
| Title : Effects of tacrine, velnacrine (HP029), suronacrine (HP128), and 3,4-diaminopyridine on skeletal neuromuscular transmission in vitro - Braga_1991_Br.J.Pharmacol_102_909 |
| Author(s) : Braga MF , Harvey AL , Rowan EG |
| Ref : British Journal of Pharmacology , 102 :909 , 1991 |
| Abstract : |
| PubMedSearch : Braga_1991_Br.J.Pharmacol_102_909 |
| PubMedID: 1649660 |
| Title : Facilitation by 3,4-diaminopyridine of regenerative acetylcholine release from mouse motor nerve - Hong_1990_Br.J.Pharmacol_101_793 |
| Author(s) : Hong SJ , Chang CC |
| Ref : British Journal of Pharmacology , 101 :793 , 1990 |
| Abstract : |
| PubMedSearch : Hong_1990_Br.J.Pharmacol_101_793 |
| PubMedID: 1964819 |
| Title : Effects of LF-14, THA and physostigmine in rat hippocampus and cerebral cortex - Potter_1989_Neurochem.Int_14_433 |
| Author(s) : Potter PE , Nitta S , Chaudhry I , Lalezari I , Goldiner P , Foldes FF |
| Ref : Neurochem Int , 14 :433 , 1989 |
| Abstract : |
| PubMedSearch : Potter_1989_Neurochem.Int_14_433 |
| PubMedID: 20504446 |
| Title : Changes in cytosolic free calcium with 1,2,3,4-tetrahydro-5-aminoacridine, 4-aminopyridine and 3,4-diaminopyridine - Gibson_1988_Biochem.Pharmacol_37_4191 |
| Author(s) : Gibson GE , Manger T |
| Ref : Biochemical Pharmacology , 37 :4191 , 1988 |
| Abstract : |
| PubMedSearch : Gibson_1988_Biochem.Pharmacol_37_4191 |
| PubMedID: 2847755 |
| Title : Aminoglycosides and 3,4-diaminopyridine on neuromuscular block caused by botulinum type A toxin - Molgo_1987_Muscle.Nerve_10_464 |
| Author(s) : Molgo J , Lemeignan M , Thesleff S |
| Ref : Muscle & Nerve , 10 :464 , 1987 |
| Abstract : |
| PubMedSearch : Molgo_1987_Muscle.Nerve_10_464 |
| PubMedID: 3497343 |
| Title : Differential alteration of dopamine, acetylcholine, and glutamate release during anoxia and\/or 3,4-diaminopyridine treatment - Freeman_1987_Neurochem.Res_12_1019 |
| Author(s) : Freeman GB , Mykytyn V , Gibson GE |
| Ref : Neurochem Res , 12 :1019 , 1987 |
| Abstract : |
| PubMedSearch : Freeman_1987_Neurochem.Res_12_1019 |
| PubMedID: 2891059 |
| Title : Spontaneous excitatory postsynaptic currents in crayfish neuromuscular junctions in the absence and presence of serotonin and 3,4-diaminopyridine - Finger_1986_J.Comp.Physiol.A_159_13 |
| Author(s) : Finger W , Martin C |
| Ref : J Comp Physiol A , 159 :13 , 1986 |
| Abstract : |
| PubMedSearch : Finger_1986_J.Comp.Physiol.A_159_13 |
| PubMedID: 3746725 |
| Title : Interactions of Calcium Homeostasis, Acetylcholine Metabolism, Behavior and 3,4-Diaminopyridine during Aging - |
| Author(s) : Gibson GE , Peterson C |
| Ref : Advances in Behavioral Biology , 30 :191 , 1986 |
| PubMedID: |
| Title : Amelioration of age-related neurochemical and behavioral deficits by 3,4-diaminopyridine - Peterson_1983_Neurobiol.Aging_4_25 |
| Author(s) : Peterson C , Gibson GE |
| Ref : Neurobiology of Aging , 4 :25 , 1983 |
| Abstract : |
| PubMedSearch : Peterson_1983_Neurobiol.Aging_4_25 |
| PubMedID: 6877484 |
| Title : Improvement of 8-arm maze performance in aged Fischer 344 rats with 3,4-diaminopyridine - Davis_1983_Exp.Aging.Res_9_211 |
| Author(s) : Davis HP , Idowu A , Gibson GE |
| Ref : Exp Aging Res , 9 :211 , 1983 |
| Abstract : |
| PubMedSearch : Davis_1983_Exp.Aging.Res_9_211 |
| PubMedID: 6641784 |
| Title : 3,4-diaminopyridine alters acetylcholine metabolism and behavior during hypoxia - Peterson_1982_J.Pharmacol.Exp.Ther_222_576 |
| Author(s) : Peterson C , Gibson GE |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 222 :576 , 1982 |
| Abstract : |
| PubMedSearch : Peterson_1982_J.Pharmacol.Exp.Ther_222_576 |
| PubMedID: 6286925 |
| Title : Potency of 3,4-diaminopyridine and 4-aminopyridine on mammalian neuromuscular transmission and the effect of pH changes - |
| Author(s) : Molgo J , Lundh H , Thesleff S |
| Ref : European Journal of Pharmacology , 61 :25 , 1980 |
| PubMedID: 6101553 |