K027

General

Type : Oxime, Bisoxime, Bispyridinium

Chemical_Nomenclature : 1-[3-[4-(oxoazaniumylmethylidene)-1H-pyridin-1-ium-1-yl]propyl]pyridin-1-ium-4-carboximidate

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

InChI : InChI=1S\/C15H16N4O2\/c16-15(20)14-4-10-19(11-5-14)7-1-6-18-8-2-13(3-9-18)12-17-21\/h2-5,8-12H,1,6-7H2,(H-,16,20)\/p+2

InChIKey : KCCVYOKFPFWMQG-UHFFFAOYSA-P

Other name(s) : 1-(4-hydroxyiminomethylpyridinium)-3-(4-carbamoylpyridinium) propane dibromide  ||  4-Carbamoyl-1-(3-{4-[(E)-(Hydroxyimino)methyl]pyridinium-1-Yl}propyl)pyridinium  ||  Tacarb  ||  K-27  ||  K27  ||  AC1NUT9P  ||  CHEMBL1185207  ||  DTXSID80230343


MW : 286.32

Formula : C15H18N4O2

CAS_number : 80466-19-9

PubChem : 5492534,    101237538

UniChem : KCCVYOKFPFWMQG-UHFFFAOYSA-P

Target

Structure : 2WHR

Families : No family

References (33)

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 : Encapsulation of oxime K027 into cucurbit[7]uril: In vivo evaluation of safety, absorption, brain distribution and reactivation effectiveness - Karasova_2020_Toxicol.Lett_320_64
Author(s) : Karasova JZ , Hepnarova V , Andrys R , Lisa M , Jost P , Muckova L , Pejchal J , Herman D , Jun D , Kassa J , Kuca K
Ref : Toxicol Lett , 320 :64 , 2020
Abstract :
PubMedSearch : Karasova_2020_Toxicol.Lett_320_64
PubMedID: 31794810

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 : Comparison of oximes K203 and K027 based on Benchmark dose analysis of rat diaphragmal acetylcholinesterase reactivation - Antonijevic_2019_Chem.Biol.Interact_13ChEPon_308_385
Author(s) : Antonijevic E , Musilek K , Kuca K , Djukic-Cosic D , Andjelkovic M , Djordjevic AB , Antonijevic B
Ref : Chemico-Biological Interactions , 308 :385 , 2019
Abstract :
PubMedSearch : Antonijevic_2019_Chem.Biol.Interact_13ChEPon_308_385
PubMedID: 31141677

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 silico and in vitro evaluation of two novel oximes (K378 and K727) in comparison to K-27 and pralidoxime against paraoxon-ethyl intoxication - Arshad_2018_Toxicol.Mech.Methods_28_62
Author(s) : Arshad M , Fatmi MQ , Musilek K , Hussain A , Kuca K , Petroianu G , Kalasz H , Nurulain SM
Ref : Toxicol Mech Methods , 28 :62 , 2018
Abstract :
PubMedSearch : Arshad_2018_Toxicol.Mech.Methods_28_62
PubMedID: 28722512

Title : Pharmacokinetic profile of promising acetylcholinesterase reactivators K027 and K203 in experimental pigs - Karasova_2017_Toxicol.Lett_273_20
Author(s) : Karasova JZ , Kvetina J , Tacheci I , Radochova V , Musilek K , Kuca K , Bures J
Ref : Toxicol Lett , 273 :20 , 2017
Abstract :
PubMedSearch : Karasova_2017_Toxicol.Lett_273_20
PubMedID: 28343895

Title : Therapeutic and reactivating efficacy of oximes K027 and K203 against a direct acetylcholinesterase inhibitor - Antonijevic_2016_Neurotoxicol_55_33
Author(s) : Antonijevic E , Musilek K , Kuca K , Djukic-Cosic D , Vucinic S , Antonijevic B
Ref : Neurotoxicology , 55 :33 , 2016
Abstract :
PubMedSearch : Antonijevic_2016_Neurotoxicol_55_33
PubMedID: 27177985

Title : Mini review on blood-brain barrier penetration of pyridinium aldoximes - Kalasz_2014_J.Appl.Toxicol_2_141
Author(s) : Kalasz H , Nurulain SM , Veress G , Antus S , Darvas F , Adeghate E , Adem A , Hashemi F , Tekes K
Ref : J Appl Toxicol , 2 :141 , 2014
Abstract :
PubMedSearch : Kalasz_2014_J.Appl.Toxicol_2_141
PubMedID: 25291712

Title : K-oxime (K-27): phosphylation-induced changes in logP - Petroianu_2014_Mil.Med.Sci.Lett_83_52
Author(s) : Petroianu GA , Athauda G , Darvas F , Kalasz H , Lorke DE
Ref : Military Medical Science Letters , 83 :52 , 2014
Abstract :
PubMedSearch : Petroianu_2014_Mil.Med.Sci.Lett_83_52
PubMedID:

Title : Mono-oxime bisquaternary acetylcholinesterase reactivators with prop-1,3-diyl linkage-Preparation, in vitro screening and molecular docking - Musilek_2011_Bioorg.Med.Chem_19_754
Author(s) : Musilek K , Komloova M , Holas O , Horova A , Pohanka M , Gunn-Moore F , Dohnal V , Dolezal M , Kuca K
Ref : Bioorganic & Medicinal Chemistry , 19 :754 , 2011
Abstract :
PubMedSearch : Musilek_2011_Bioorg.Med.Chem_19_754
PubMedID: 21215642

Title : The effect of oxime reactivators on muscarinic receptors: functional and binding examinations - Soukup_2011_Environ.Toxicol.Pharmacol_31_364
Author(s) : Soukup O , Kumar UK , Proska J , Bratova L , Adem A , Jun D , Fusek J , Kuca K , Tobin G
Ref : Environ Toxicol Pharmacol , 31 :364 , 2011
Abstract :
PubMedSearch : Soukup_2011_Environ.Toxicol.Pharmacol_31_364
PubMedID: 21787706

Title : Oxime reactivators and their in vivo and in vitro effects on nicotinic receptors - Soukup_2011_Physiol.Res_60_679
Author(s) : Soukup O , Krusek J , Kaniakova M , Kumar UK , Oz M , Jun D , Fusek J , Kuca K , Tobin G
Ref : Physiol Res , 60 :679 , 2011
Abstract :
PubMedSearch : Soukup_2011_Physiol.Res_60_679
PubMedID: 21574759

Title : The antidotal efficacy of the bispyridinium oximes K027 and TMB-4 against tabun poisoning in mice - Berend_2010_Chem.Biol.Interact_187_291
Author(s) : Zunec S , Radic B , Kuca K , Lucic Vrdoljak A
Ref : Chemico-Biological Interactions , 187 :291 , 2010
Abstract :
PubMedSearch : Berend_2010_Chem.Biol.Interact_187_291
PubMedID: 20138854

Title : Oxime K027: novel low-toxic candidate for the universal reactivator of nerve agent- and pesticide-inhibited acetylcholinesterase - Kuca_2010_J.Enzyme.Inhib.Med.Chem_25_509
Author(s) : Kuca K , Musilek K , Jun D , Pohanka M , Ghosh KK , Hrabinova M
Ref : J Enzyme Inhib Med Chem , 25 :509 , 2010
Abstract :
PubMedSearch : Kuca_2010_J.Enzyme.Inhib.Med.Chem_25_509
PubMedID: 20192902

Title : Reactivation of tabun-hAChE investigated by structurally analogous oximes and mutagenesis - Artursson_2009_Toxicology_265_108
Author(s) : Artursson E , Akfur C , Hornberg A , Worek F , Ekstrom F
Ref : Toxicology , 265 :108 , 2009
Abstract :
PubMedSearch : Artursson_2009_Toxicology_265_108
PubMedID: 19761810

Title : Structure of HI-6*sarin-acetylcholinesterase determined by X-ray crystallography and molecular dynamics simulation: reactivator mechanism and design - Ekstrom_2009_PLoS.One_4_e5957
Author(s) : Ekstrom F , Hornberg A , Artursson E , Hammarstrom LG , Schneider G , Pang YP
Ref : PLoS ONE , 4 :e5957 , 2009
Abstract :
PubMedSearch : Ekstrom_2009_PLoS.One_4_e5957
PubMedID: 19536291
Gene_locus related to this paper: mouse-ACHE

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 : 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 : Measurement of K-27, an oxime-type cholinesterase reactivator by high-performance liquid chromatography with electrochemical detection from different biological samples - Gyenge_2007_J.Chromatogr.A_1161_146
Author(s) : Gyenge M , Kalasz H , Petroianu GA , Laufer R , Kuca K , Tekes K
Ref : Journal of Chromatography A , 1161 :146 , 2007
Abstract :
PubMedSearch : Gyenge_2007_J.Chromatogr.A_1161_146
PubMedID: 17603065

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 : In vitro reactivation of acetylcholinesterase using the oxime K027 - Kuca_2004_Vet.Hum.Toxicol_46_15
Author(s) : Kuca K , Kassa J
Ref : Vet Hum Toxicol , 46 :15 , 2004
Abstract :
PubMedSearch : Kuca_2004_Vet.Hum.Toxicol_46_15
PubMedID: 14748409

Title : Oximes-induced reactivation of rat brain acetylcholinesterase inhibited by VX agent - Kuca_2004_Hum.Exp.Toxicol_23_167
Author(s) : Kuca K , Kassa J
Ref : Hum Exp Toxicol , 23 :167 , 2004
Abstract :
PubMedSearch : Kuca_2004_Hum.Exp.Toxicol_23_167
PubMedID: 15171567