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
Target
Structure : No structure
Families : No family
References (36)
| Title : Halogenated monopyridinium oximes are less effective in reactivation of phosphylated cholinesterases than bisquaternary oximes - Kohoutova_2024_Bioorg.Chem_153_107904 |
| Author(s) : Kohoutova Z , Prchalova E , Andrys R , Knittelova K , Formanova M , Hofmanova T , Psotka M , Musilek K , Derat E , Malinak D |
| Ref : Bioorg Chem , 153 :107904 , 2024 |
| Abstract : |
| PubMedSearch : Kohoutova_2024_Bioorg.Chem_153_107904 |
| PubMedID: 39467508 |
| 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 , Macek Hrvat N , 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 : 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 : 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 : 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 : 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 : 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 : 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 |