K048

General

Type : Bispyridinium, Oxime

Chemical_Nomenclature : [1-[4-(4-carbamoylpyridin-1-ium-1-yl)butyl]pyridin-4-ylidene]methyl-oxoazanium

Canonical SMILES : C1=CN(C=CC1=C[NH+]=O)CCCC[N+]2=CC=C(C=C2)C(=O)N

InChI : InChI=1S\/C16H18N4O2\/c17-16(21)15-5-11-20(12-6-15)8-2-1-7-19-9-3-14(4-10-19)13-18-22\/h3-6,9-13H,1-2,7-8H2,(H-,17,21)\/p+2

InChIKey : KMFIVIQDYRPBBJ-UHFFFAOYSA-P

Other name(s) : 1-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium) butane dibromide  ||  K-48  ||  CHEMBL1180193


MW : 300.35

Formula : C16H20N4O2

CAS_number :

PubChem : 90659972

UniChem : KMFIVIQDYRPBBJ-UHFFFAOYSA-P

Target

Structure : No structure

Families : No family

References (26)

Title : In Vitro Evaluation of Oxidative Stress Induced by Oxime Reactivators of Acetylcholinesterase in HepG2 Cells - Vanova_2023_Chem.Res.Toxicol__
Author(s) : Vanova N , Muckova L , Kaliskova T , Lochman L , Bzonek P , Svec F
Ref : Chemical Research in Toxicology , : , 2023
Abstract :
PubMedSearch : Vanova_2023_Chem.Res.Toxicol__
PubMedID: 37950699

Title : Halogen substituents enhance oxime nucleophilicity for reactivation of cholinesterases inhibited by nerve agents - Zorbaz_2022_Eur.J.Med.Chem_238_114377
Author(s) : Zorbaz T , Malinak D , Hofmanova T , Marakovic N , Zunec S , Hrvat NM , Andrys R , Psotka M , Zandona A , Svobodova J , Prchal L , Fingler S , Katalinic M , Kovarik Z , Musilek K
Ref : Eur Journal of Medicinal Chemistry , 238 :114377 , 2022
Abstract :
PubMedSearch : Zorbaz_2022_Eur.J.Med.Chem_238_114377
PubMedID: 35526478

Title : Determination of K869, a novel oxime reactivator of acetylcholinesterase, in rat body fluids and tissues by liquid-chromatography methods: Pharmacokinetic study - Vanova_2021_J.Pharm.Sci__
Author(s) : Vanova N , Hojna A , Pejchal J , Herman D , Malinak D , Prchalova E , Musilek K , Karasova JZ
Ref : J Pharm Sci , : , 2021
Abstract :
PubMedSearch : Vanova_2021_J.Pharm.Sci__
PubMedID: 33545185

Title : The Experimental Oxime K027-A Promising Protector From Organophosphate Pesticide Poisoning. A Review Comparing K027, K048, Pralidoxime, and Obidoxime - Lorke_2019_Front.Neurosci_13_427
Author(s) : Lorke DE , Petroianu GA
Ref : Front Neurosci , 13 :427 , 2019
Abstract :
PubMedSearch : Lorke_2019_Front.Neurosci_13_427
PubMedID: 31191210

Title : Interspecies and intergender differences in acute toxicity of K-oximes drug candidates - Jacevic_2019_Chem.Biol.Interact_13ChEPon_308_312
Author(s) : Jacevic V , Nepovimova E , Kuca K
Ref : Chemico-Biological Interactions , 308 :312 , 2019
Abstract :
PubMedSearch : Jacevic_2019_Chem.Biol.Interact_13ChEPon_308_312
PubMedID: 31153983

Title : Pyridinium Oximes with Ortho-Positioned Chlorine Moiety Exhibit Improved Physicochemical Properties and Efficient Reactivation of Human Acetylcholinesterase Inhibited by Several Nerve Agents - Zorbaz_2018_J.Med.Chem_61_10753
Author(s) : Zorbaz T , Malinak D , Marakovic N , Macek Hrvat N , Zandona A , Novotny M , Skarka A , Andrys R , Benkova M , Soukup O , Katalinic M , Kuca K , Kovarik Z , Musilek K
Ref : Journal of Medicinal Chemistry , 61 :10753 , 2018
Abstract :
PubMedSearch : Zorbaz_2018_J.Med.Chem_61_10753
PubMedID: 30383374

Title : In vivo evaluation of cholinesterase activity, oxidative stress markers, cyto- and genotoxicity of K048 oxime-a promising antidote against organophosphate poisoning - Zunec_2014_Basic.Clin.Pharmacol.Toxicol_114_344
Author(s) : Zunec S , Kopjar N , Zeljezic D , Kuca K , Musilek K , Lucic Vrdoljak A
Ref : Basic Clin Pharmacol Toxicol , 114 :344 , 2014
Abstract :
PubMedSearch : Zunec_2014_Basic.Clin.Pharmacol.Toxicol_114_344
PubMedID: 24741714

Title : Reactivation of Tabun-inhibited Acetylcholinesterase Investigated by Two Oximes and Mutagenesis - Katalinic_2012_Croatica.Chem.Acta_85_209
Author(s) : Katalinic M , Kovarik Z
Ref : Croatica Chemica Acta , 85 :209\ , 2012
Abstract :
PubMedSearch : Katalinic_2012_Croatica.Chem.Acta_85_209
PubMedID:

Title : A comparison of tabun-inhibited rat brain acetylcholinesterase reactivation by three oximes (HI-6, obidoxime, and K048) in vivo detected by biochemical and histochemical techniques - Bajgar_2010_J.Enzyme.Inhib.Med.Chem_25_790
Author(s) : Bajgar J , Hajek P , Karasova JZ , Kassa J , Paseka A , Slizova D , Krs O , Kuca K , Jun D , Fusek J , Capek L
Ref : J Enzyme Inhib Med Chem , 25 :790 , 2010
Abstract :
PubMedSearch : Bajgar_2010_J.Enzyme.Inhib.Med.Chem_25_790
PubMedID: 21054236

Title : In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048 - Pohanka_2009_J.Enzyme.Inhib.Med.Chem_24_680
Author(s) : Pohanka M , Jun D , Kuca K
Ref : J Enzyme Inhib Med Chem , 24 :680 , 2009
Abstract :
PubMedSearch : Pohanka_2009_J.Enzyme.Inhib.Med.Chem_24_680
PubMedID: 18825528

Title : Effect of acetylcholinesterase oxime-type reactivators K-48 and HI-6 on human liver microsomal cytochromes P450 in vitro - Veinlichova_2009_Chem.Biol.Interact_180_449
Author(s) : Veinlichova A , Jancova P , Siller M , Anzenbacher P , Kuca K , Jun D , Fusek J , Anzenbacherova E
Ref : Chemico-Biological Interactions , 180 :449 , 2009
Abstract :
PubMedSearch : Veinlichova_2009_Chem.Biol.Interact_180_449
PubMedID: 19539805

Title : Comments on Efficacy of two new asymmetric bispyridinium oximes (K-27 and K-48) in rats exposed to diisopropylfluorophosphate: comparison with pralidoxime, obidoxime, trimedoxime, methoxime, and HI 6 -
Author(s) : Theirmann H , Worek F , Eyer P
Ref : Toxicol Mech Methods , 19 :334\; author reply 335 , 2009
PubMedID: 19778225

Title : Efficacy of two new asymmetric bispyridinium oximes (K-27 and K-48) in rats exposed to diisopropylfluorophosphate: comparison with pralidoxime, obidoxime, trimedoxime, methoxime, and HI-6 - Lorke_2009_Toxicol.Mech.Methods_19_327
Author(s) : Lorke DE , Hasan MY , Nurulain SM , Kuca K , Schmitt A , Petroianu GA
Ref : Toxicol Mech Methods , 19 :327 , 2009
Abstract :
PubMedSearch : Lorke_2009_Toxicol.Mech.Methods_19_327
PubMedID: 19778224

Title : Synthesis of monooxime-monocarbamoyl bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against tabun- and paraoxon-inhibited acetylcholinesterase - Musilek_2008_J.Enzyme.Inhib.Med.Chem_23_70
Author(s) : Musilek K , Holas O , Kuca K , Jun D , Dohnal V , Opletalova V , Dolezal M
Ref : J Enzyme Inhib Med Chem , 23 :70 , 2008
Abstract :
PubMedSearch : Musilek_2008_J.Enzyme.Inhib.Med.Chem_23_70
PubMedID: 18341256

Title : Temporal effects of newly developed oximes (K027, K048) on malathion-induced acetylcholinesterase inhibition and lipid peroxidation in mouse prefrontal cortex - da Silva_2008_Neurotoxicol_29_184
Author(s) : da Silva AP , Farina M , Franco JL , Dafre AL , Kassa J , Kuca K
Ref : Neurotoxicology , 29 :184 , 2008
Abstract :
PubMedSearch : da Silva_2008_Neurotoxicol_29_184
PubMedID: 18035420

Title : Five oximes (K-27, K-48, obidoxime, HI-6 and trimedoxime) in comparison with pralidoxime: survival in rats exposed to methyl-paraoxon - Petroianu_2007_J.Appl.Toxicol_27_453
Author(s) : Petroianu GA , Nurulain SM , Nagelkerke N , Shafiullah M , Kassa J , Kuca K
Ref : J Appl Toxicol , 27 :453 , 2007
Abstract :
PubMedSearch : Petroianu_2007_J.Appl.Toxicol_27_453
PubMedID: 17304644

Title : A comparison of the efficacy of new asymmetric bispyridinium oximes (K027, K048) with currently available oximes against tabun by in vivo methods - Kassa_2006_J.Toxicol.Environ.Health.A_69_1875
Author(s) : Kassa J , Kuca K , Cabal J , Paar M
Ref : J Toxicol Environ Health A , 69 :1875 , 2006
Abstract :
PubMedSearch : Kassa_2006_J.Toxicol.Environ.Health.A_69_1875
PubMedID: 16952906

Title : In vitro and in vivo evaluation of pyridinium oximes: mode of interaction with acetylcholinesterase, effect on tabun- and soman-poisoned mice and their cytotoxicity - Calic_2006_Toxicology_219_85
Author(s) : Calic M , Vrdoljak AL , Radic B , Jelic D , Jun D , Kuca K , Kovarik Z
Ref : Toxicology , 219 :85 , 2006
Abstract :
PubMedSearch : Calic_2006_Toxicology_219_85
PubMedID: 16332406

Title : Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: in vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon - Petroianu_2006_J.Appl.Toxicol_26_64
Author(s) : Petroianu GA , Arafat K , Kuca K , Kassa J
Ref : J Appl Toxicol , 26 :64 , 2006
Abstract :
PubMedSearch : Petroianu_2006_J.Appl.Toxicol_26_64
PubMedID: 16193529

Title : Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: survival in rats exposed to the organophosphate paraoxon - Petroianu_2006_J.Appl.Toxicol_26_262
Author(s) : Petroianu GA , Nurulain SM , Nagelkerke N , Al-Sultan MA , Kuca K , Kassa J
Ref : J Appl Toxicol , 26 :262 , 2006
Abstract :
PubMedSearch : Petroianu_2006_J.Appl.Toxicol_26_262
PubMedID: 16583462

Title : A comparison of the potency of newly developed oximes (K005, K027, K033, K048) and currently used oximes (pralidoxime, obidoxime, HI-6) to reactivate sarin-inhibited rat brain acetylcholinesterase by in vitro methods - Kuca_2005_J.Toxicol.Environ.Health.A_68_677
Author(s) : Kuca K , Cabal J , Kassa J
Ref : J Toxicol Environ Health A , 68 :677 , 2005
Abstract :
PubMedSearch : Kuca_2005_J.Toxicol.Environ.Health.A_68_677
PubMedID: 15901095

Title : New quaternary pyridine aldoximes as casual antidotes against nerve agents intoxications - Kuca_2005_Biomed.Pap.Med.Fac.Univ.Palacky.Olomouc.Czech.Repub_149_75
Author(s) : Kuca K , Bartosova L , Jun D , Patocka J , Cabal J , Kassa J , Kunesova G
Ref : Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub , 149 :75 , 2005
Abstract :
PubMedSearch : Kuca_2005_Biomed.Pap.Med.Fac.Univ.Palacky.Olomouc.Czech.Repub_149_75
PubMedID: 16170392

Title : [A comparison of the efficacy of the reactivators of acetylcholinesterase inhibited with tabun] - Cabal_2005_Ceska.Slov.Farm_54_192
Author(s) : Cabal J , Kuca K , Jun D , Bajgar J , Hrabinova M
Ref : Ceska a Slovenska Farmacie , 54 :192 , 2005
Abstract :
PubMedSearch : Cabal_2005_Ceska.Slov.Farm_54_192
PubMedID: 16124202

Title : In vitro reactivation of acetylcholinesterase inhibited by cyclosarin using bisquaternary pyridinium aldoximes K005, K033, K027 AND K048 - Kuca_2004_Acta.Medica.(Hradec.Kralove)_47_107
Author(s) : Kuca K , Sevelova-Bartosova L , Krejcova-Kunesova G
Ref : Acta Medica (Hradec Kralove) , 47 :107 , 2004
Abstract :
PubMedSearch : Kuca_2004_Acta.Medica.(Hradec.Kralove)_47_107
PubMedID: 15446359

Title : In vitro reactivation of tabun-inhibited acetylcholinesterase using new oximes--K027, K005, K033 and K048 - Kuca_2004_Cent.Eur.J.Public.Health_12 Suppl_S59
Author(s) : Kuca K , Cabal J
Ref : Central European Journal of Public Health , 12 Suppl :S59 , 2004
Abstract :
PubMedSearch : Kuca_2004_Cent.Eur.J.Public.Health_12 Suppl_S59
PubMedID: 15141981

Title : A comparison of the ability of a new bispyridinium oxime--1-(4-hydroxyiminomethylpyridinium)-4-(4-carbamoylpyridinium)butane dibromide and currently used oximes to reactivate nerve agent-inhibited rat brain acetylcholinesterase by in vitro methods - Kuca_2003_J.Enzyme.Inhib.Med.Chem_18_529
Author(s) : Kuca K , Kassa J
Ref : J Enzyme Inhib Med Chem , 18 :529 , 2003
Abstract :
PubMedSearch : Kuca_2003_J.Enzyme.Inhib.Med.Chem_18_529
PubMedID: 15008517