K203

General

Type : Oxime, Bispyridinium

Chemical_Nomenclature : [1-[(E)-4-(4-carbamoylpyridin-1-ium-1-yl)but-2-enyl]pyridin-4-ylidene]methyl-oxoazanium

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

InChI : InChI=1S\/C16H16N4O2\/c17-16(21)15-5-11-20(12-6-15)8-2-1-7-19-9-3-14(4-10-19)13-18-22\/h1-6,9-13H,7-8H2,(H-,17,21)\/p+2\/b2-1+

InChIKey : UILZOFLNCNKRGW-OWOJBTEDSA-P

Other name(s) : (E)-1-(4-carbamoylpyridinium)-4-(4-hydroxyiminomethyl-pyridinium)-but-2-ene dibromide  ||  K-203  ||  CHEMBL1182443  ||  STL301833  ||  ZINC28861846  ||  AKOS022133526  ||  4-carbamoyl-1-[(2E)-4-{4-[(E)-(hydroxyimino)methyl]pyridinium-1-yl}but-2-en-1-yl]pyridinium  ||  AKOS016372534  ||  HY-146959  ||  CS-0459568


MW : 298.33

Formula : C16H18N4O2

CAS_number :

PubChem : 71700369,    135846071

UniChem : UILZOFLNCNKRGW-OWOJBTEDSA-P

Target

Structure : No structure

Families : No family

References (35)

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 : 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 : Slight difference in the isomeric oximes K206 and K203 makes huge difference for the reactivation of organophosphorus-inhibited AChE: Theoretical and experimental aspects - Polisel_2019_Chem.Biol.Interact_13ChEPon_309_108671
Author(s) : Polisel DA , de Castro AA , Mancini DT , da Cunha EFF , Franca TCC , Ramalho TC , Kuca K
Ref : Chemico-Biological Interactions , 309 :108671 , 2019
Abstract :
PubMedSearch : Polisel_2019_Chem.Biol.Interact_13ChEPon_309_108671
PubMedID: 31207225

Title : Oxime K203: a drug candidate for the treatment of tabun intoxication - Gorecki_2019_Arch.Toxicol_93_673
Author(s) : Gorecki L , Soukup O , Kucera T , Malinak D , Jun D , Kuca K , Musilek K , Korabecny J
Ref : Archives of Toxicology , 93 :673 , 2019
Abstract :
PubMedSearch : Gorecki_2019_Arch.Toxicol_93_673
PubMedID: 30564897

Title : A newly developed oxime K203 is the most effective reactivator of tabun-inhibited acetylcholinesterase - Kuca_2018_BMC.Pharmacol.Toxicol_19_8
Author(s) : Kuca K , Musilek K , Jun D , Karasova JZ , Nepovimova E , Soukup O , Hrabinova M , Mikler J , Franca TCC , da Cunha EFF , de Castro AA , Valis M , Ramalho TC
Ref : BMC Pharmacol Toxicol , 19 :8 , 2018
Abstract :
PubMedSearch : Kuca_2018_BMC.Pharmacol.Toxicol_19_8
PubMedID: 29467029

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 : 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 : A comparison of the reactivating and therapeutic efficacy of two newly developed oximes (K727 and K733) with oxime k203 and trimedoxime in tabun-poisoned rats and mice - Kassa_2015_Basic.Clin.Pharmacol.Toxicol_116_367
Author(s) : Kassa J , Sepsova V , Tumova M , Horova A , Musilek K
Ref : Basic Clin Pharmacol Toxicol , 116 :367 , 2015
Abstract :
PubMedSearch : Kassa_2015_Basic.Clin.Pharmacol.Toxicol_116_367
PubMedID: 25225130

Title : Universality of Oxime K203 for Reactivation of Nerve Agent-Inhibited AChE - Kuca_2015_Med.Chem_11_683
Author(s) : Kuca K , Hrabinova M , Jun D , Musilek K , Penhaker M , Krejcar O , Soukup O
Ref : Med Chem , 11 :683 , 2015
Abstract :
PubMedSearch : Kuca_2015_Med.Chem_11_683
PubMedID: 25845909

Title : In vitro reactivation kinetics of paraoxon- and DFP-inhibited electric eel AChE using mono- and bis-pyridinium oximes - Gupta_2014_Arch.Toxicol_88_381
Author(s) : Gupta B , Sharma R , Singh N , Kuca K , Acharya JR , Ghosh KK
Ref : Archives of Toxicology , 88 :381 , 2014
Abstract :
PubMedSearch : Gupta_2014_Arch.Toxicol_88_381
PubMedID: 24065055

Title : The evaluation of the reactivating and therapeutic efficacy of two novel oximes (K361 and K378) in comparison with the oxime K203 and trimedoxime in tabun-poisoned rats and mice - Kassa_2014_Toxicol.Mech.Methods_24_173
Author(s) : Kassa J , Sepsova V , Tumova M , Musilek K , Horova A
Ref : Toxicol Mech Methods , 24 :173 , 2014
Abstract :
PubMedSearch : Kassa_2014_Toxicol.Mech.Methods_24_173
PubMedID: 24295433

Title : The evaluation of the reactivating and therapeutic efficacy of three novel bispyridinium oximes (K454, K456, K458) in comparison with the oxime K203 and trimedoxime in tabun-poisoned rats and mice - Kassa_2013_Toxicol.Mech.Methods_23_94
Author(s) : Kassa J , Sepsova V , Musilek K , Horova A
Ref : Toxicol Mech Methods , 23 :94 , 2013
Abstract :
PubMedSearch : Kassa_2013_Toxicol.Mech.Methods_23_94
PubMedID: 22901042

Title : Combined approach to demonstrate acetylcholinesterase activity changes in the rat brain following tabun intoxication and its treatment - Bajgar_2012_Toxicol.Mech.Methods_22_60
Author(s) : Bajgar J , Hajek P , Kassa J , Slizova D , Krs O , Karasova JZ , Fusek J , Capek L , Voicu VA
Ref : Toxicol Mech Methods , 22 :60 , 2012
Abstract :
PubMedSearch : Bajgar_2012_Toxicol.Mech.Methods_22_60
PubMedID: 21851296

Title : The ability of oxime mixtures to increase the reactivating and therapeutic efficacy of antidotal treatment of cyclosarin poisoning in rats and mice - Kassa_2012_Acta.Medica.(Hradec.Kralove)_55_27
Author(s) : Kassa J , Karasova JZ , Pavlikova R , Caisberger F , Bajgar J
Ref : Acta Medica (Hradec Kralove) , 55 :27 , 2012
Abstract :
PubMedSearch : Kassa_2012_Acta.Medica.(Hradec.Kralove)_55_27
PubMedID: 22696932

Title : Two possibilities how to increase the efficacy of antidotal treatment of nerve agent poisonings - Kassa_2012_Mini.Rev.Med.Chem_12_24
Author(s) : Kassa J , Musilek K , Karasova JZ , Kuca K , Bajgar J
Ref : Mini Rev Med Chem , 12 :24 , 2012
Abstract :
PubMedSearch : Kassa_2012_Mini.Rev.Med.Chem_12_24
PubMedID: 22360668

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 : Biochemical insight into soman intoxication and treatment with atropine, HI-6, trimedoxime, and K203 in a rat model - Pohanka_2011_Bratisl.Lek.Listy_112_539
Author(s) : Pohanka M , Pikula J , Kuca K , Kassa J
Ref : Bratislavske Lekarske Listy , 112 :539 , 2011
Abstract :
PubMedSearch : Pohanka_2011_Bratisl.Lek.Listy_112_539
PubMedID: 21954536

Title : The benefit of combinations of oximes for the reactivating and therapeutic efficacy of antidotal treatment of sarin poisoning in rats and mice - Kassa_2011_Basic.Clin.Pharmacol.Toxicol_109_30
Author(s) : Kassa J , Karasova JZ , Sepsova V , Caisberger F
Ref : Basic Clin Pharmacol Toxicol , 109 :30 , 2011
Abstract :
PubMedSearch : Kassa_2011_Basic.Clin.Pharmacol.Toxicol_109_30
PubMedID: 21235715

Title : A comparison of the reactivating and therapeutic efficacy of chosen combinations of oximes with individual oximes against VX in rats and mice - Kassa_2011_Int.J.Toxicol_30_562
Author(s) : Kassa J , Karasova JZ , Sepsova V , Caisberger F , Bajgar J
Ref : Int J Toxicol , 30 :562 , 2011
Abstract :
PubMedSearch : Kassa_2011_Int.J.Toxicol_30_562
PubMedID: 22013137

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 : A Comparison of Neuroprotective Efficacy of the Oxime K203 and its Fluorinated Analogue (KR-22836) with Obidoxime in Tabun-Poisoned Rats - Kassa_2010_Basic.Clin.Pharmacol.Toxicol_107_861
Author(s) : Kassa J , Karasova JZ , Tesarova S , Musilek K , Kuca K , Jung YS
Ref : Basic Clin Pharmacol Toxicol , 107 :861 , 2010
Abstract :
PubMedSearch : Kassa_2010_Basic.Clin.Pharmacol.Toxicol_107_861
PubMedID: 22545968

Title : A comparison of reactivating and therapeutic efficacy of the oxime K203 and its fluorinated analog (KR-22836) with currently available oximes (obidoxime, trimedoxime, HI-6) against tabun in rats and mice - Kassa_2010_J.Enzyme.Inhib.Med.Chem_25_480
Author(s) : Kassa J , Karasova JZ , Caisberger F , Musilek K , Kuca K , Jung YS
Ref : J Enzyme Inhib Med Chem , 25 :480 , 2010
Abstract :
PubMedSearch : Kassa_2010_J.Enzyme.Inhib.Med.Chem_25_480
PubMedID: 20233085

Title : Monooxime-monocarbamoyl Bispyridinium Xylene-Linked Reactivators of Acetylcholinesterase-Synthesis, In vitro and Toxicity Evaluation, and Docking Studies - Musilek_2010_ChemMedChem_5_247
Author(s) : Musilek K , Holas O , Misik J , Pohanka M , Novotny L , Dohnal V , Opletalova V , Kuca K
Ref : ChemMedChem , 5 :247 , 2010
Abstract :
PubMedSearch : Musilek_2010_ChemMedChem_5_247
PubMedID: 20058292

Title : Interactions of pyridinium oximes with acetylcholinesterase - Sinko_2010_Chem.Biol.Interact_187_172
Author(s) : Sinko G , Brglez J , Kovarik Z
Ref : Chemico-Biological Interactions , 187 :172 , 2010
Abstract :
PubMedSearch : Sinko_2010_Chem.Biol.Interact_187_172
PubMedID: 20417629

Title : The influence of combinations of oximes on the reactivating and therapeutic efficacy of antidotal treatment of tabun poisoning in rats and mice - Kassa_2010_J.Appl.Toxicol_30_120
Author(s) : Kassa J , Karasova JZ , Pavlikova R , Misik J , Caisberger F , Bajgar J
Ref : J Appl Toxicol , 30 :120 , 2010
Abstract :
PubMedSearch : Kassa_2010_J.Appl.Toxicol_30_120
PubMedID: 19746406

Title : A comparison of reactivating and therapeutic efficacy of newly-developed oximes (K156, K203) and commonly used oximes (obidoxime, HI-6) in cyclosarin-poisoned rats and mice - Kassa_2009_Toxicol.Mech.Methods_19_346
Author(s) : Kassa J , Karasova JZ , Musilek K , Kuca K
Ref : Toxicol Mech Methods , 19 :346 , 2009
Abstract :
PubMedSearch : Kassa_2009_Toxicol.Mech.Methods_19_346
PubMedID: 19778210

Title : Evaluation of oxime k203 as antidote in tabun poisoning - Kovarik_2009_Arh.Hig.Rada.Toksikol_60_19
Author(s) : Kovarik Z , Vrdoljak AL , Zunec S , Katalinic M , Kuc K , Musilek K , Radic B
Ref : Arh Hig Rada Toksikol , 60 :19 , 2009
Abstract :
PubMedSearch : Kovarik_2009_Arh.Hig.Rada.Toksikol_60_19
PubMedID: 19329372

Title : Effect of seven newly synthesized and currently available oxime cholinesterase reactivators on cyclosarin-intoxicated rats - Karasova_2009_Int.J.Mol.Sci_10_3065
Author(s) : Karasova JZ , Kassa J , Musilek K , Pohanka M , Novotny L , Kuca K
Ref : Int J Mol Sci , 10 :3065 , 2009
Abstract :
PubMedSearch : Karasova_2009_Int.J.Mol.Sci_10_3065
PubMedID: 19742125

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 : An evaluation of therapeutic and reactivating effects of newly developed oximes (K156, K203) and commonly used oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice - Kassa_2008_Toxicology_243_311
Author(s) : Kassa J , Karasova J , Musilek K , Kuca K
Ref : Toxicology , 243 :311 , 2008
Abstract :
PubMedSearch : Kassa_2008_Toxicology_243_311
PubMedID: 18054821

Title : Design of a potent reactivator of tabun-inhibited acetylcholinesterase--synthesis and evaluation of (E)-1-(4-carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibromide (K203) - Musilek_2007_J.Med.Chem_50_5514
Author(s) : Musilek K , Jun D , Cabal J , Kassa J , Gunn-Moore F , Kuca K
Ref : Journal of Medicinal Chemistry , 50 :5514 , 2007
Abstract :
PubMedSearch : Musilek_2007_J.Med.Chem_50_5514
PubMedID: 17924614

Title : Monooxime reactivators of acetylcholinesterase with (E)-but-2-ene linker: preparation and reactivation of tabun- and paraoxon-inhibited acetylcholinesterase - Musilek_2007_Bioorg.Med.Chem_15_6733
Author(s) : Musilek K , Holas O , Jun D , Dohnal V , Gunn-Moore F , Opletalova V , Dolezal M , Kuca K
Ref : Bioorganic & Medicinal Chemistry , 15 :6733 , 2007
Abstract :
PubMedSearch : Musilek_2007_Bioorg.Med.Chem_15_6733
PubMedID: 17764957