RS194B
General
Type : Uncharged Oxime, Oxime, Azepane
Chemical_Nomenclature : N-[2-(azepan-1-yl)ethyl]-2-hydroxyiminoacetamide
Canonical SMILES : C1CCCN(CC1)CCNC(=O)C=NO
InChI : InChI=1S\/C10H19N3O2\/c14-10(9-12-15)11-5-8-13-6-3-1-2-4-7-13\/h9,15H,1-8H2,(H,11,14)
InChIKey : VIABFASHQHHYNB-UHFFFAOYSA-N
Other name(s) : RS-194B || AC1OAKUK || Oprea1_728133 || SCHEMBL15963820 || MCULE-3450389482 || 2-(Hydroxyimino)-iV-(2-(azepan-l-yl)ethyl)acetamide
MW : 214.5
Formula : C10H19N3O2
CAS_number :
PubChem : 6831267
UniChem : VIABFASHQHHYNB-UHFFFAOYSA-N
References (18)
| Title : A single post-exposure oxime RS194B treatment rapidly reactivates acetylcholinesterase and reverses acute symptoms in macaques exposed to diethylphosphorothioate parathion and chlorpyrifos insecticides - Rosenberg_2023_J.Neurochem_17thISCM_ |
| Author(s) : Rosenberg YJ , Garcia K , Diener J , Sullivan D , Donahue S , Mao L , Lees J , Jiang X , Urban LA , Momper JD , Ho KY , Taylor P |
| Ref : Journal of Neurochemistry , : , 2023 |
| Abstract : |
| PubMedSearch : Rosenberg_2023_J.Neurochem_17thISCM_ |
| PubMedID: 36786545 |
| Title : Covalent inhibition of hAChE by organophosphates causes homodimer dissociation through long-range allosteric effects - Blumenthal_2021_J.Biol.Chem__ |
| Author(s) : Blumenthal DK , Cheng X , Fajer M , Ho KY , Rohrer J , Gerlits O , Taylor P , Juneja P , Kovalevsky A , Radic Z |
| Ref : Journal of Biological Chemistry , :101007 , 2021 |
| Abstract : |
| PubMedSearch : Blumenthal_2021_J.Biol.Chem__ |
| PubMedID: 34324828 |
| Gene_locus related to this paper: human-ACHE |
| Title : Enhancing target tissue levels and diminishing plasma clearance of ionizing zwitterionic antidotes in organophosphate exposures - Shyong_2021_J.Pharmacol.Exp.Ther__ |
| Author(s) : Shyong YJ , Sepulveda Y , Garcia A , Samskey NM , Radic Z , Sit R , Sharpless KB , Momper JD , Taylor P |
| Ref : Journal of Pharmacology & Experimental Therapeutics , : , 2021 |
| Abstract : |
| PubMedSearch : Shyong_2021_J.Pharmacol.Exp.Ther__ |
| PubMedID: 34145064 |
| Title : Molecular Modeling Study of Uncharged Oximes Compared to HI-6 and 2-PAM Inside Human AChE Sarin and VX Conjugates - Souza_2020_ACS.Omega_5_4490 |
| Author(s) : Souza FR , Rodrigues Garcia D , Cuya T , Pimentel AS , Goncalves ADS , Alencastro RB , Franca TCC |
| Ref : ACS Omega , 5 :4490 , 2020 |
| Abstract : |
| PubMedSearch : Souza_2020_ACS.Omega_5_4490 |
| PubMedID: 32175496 |
| Title : Rational design, synthesis and evaluation of uncharged, smart bis-oxime antidotes of organophosphate-inhibited human acetylcholinesterase - Gorecki_2020_J.Biol.Chem_295_4079 |
| Author(s) : Gorecki L , Gerlits O , Kong X , Cheng X , Blumenthal DK , Taylor P , Ballatore C , Kovalevsky A , Radic Z |
| Ref : Journal of Biological Chemistry , 295 :4079 , 2020 |
| Abstract : |
| PubMedSearch : Gorecki_2020_J.Biol.Chem_295_4079 |
| PubMedID: 32019865 |
| Gene_locus related to this paper: human-ACHE |
| Title : Positron emission tomography evaluation of oxime countermeasures in live rats using the tracer O-(2-[(18) F]fluoroethyl)-O-(p-nitrophenyl)methylphosphonate [(18) F]-VXS - Hayes_2020_Ann.N.Y.Acad.Sci__ |
| Author(s) : Hayes TR , Blecha JE , Chao CK , Huynh TL , VanBrocklin HD , Zinn KR , Taylor P , Gerdes JM , Thompson CM |
| Ref : Annals of the New York Academy of Sciences , : , 2020 |
| Abstract : |
| PubMedSearch : Hayes_2020_Ann.N.Y.Acad.Sci__ |
| PubMedID: 32436233 |
| Title : Assessment of ionizable, zwitterionic oximes as reactivating antidotal agents for organophosphate exposure - Taylor_2019_Chem.Biol.Interact_13ChEPon_308_194 |
| Author(s) : Taylor P , Yan-Jye S , Momper J , Hou W , Camacho-Hernandez GA , Radic Z , Rosenberg YJ , Kovarik Z , Sit R , Sharpless KB |
| Ref : Chemico-Biological Interactions , 308 :194 , 2019 |
| Abstract : |
| PubMedSearch : Taylor_2019_Chem.Biol.Interact_13ChEPon_308_194 |
| PubMedID: 31100277 |
| Title : Influence of gauche effect on uncharged oxime reactivators for the reactivation of tabun-inhibited AChE: quantum chemical and steered molecular dynamics studies - Ghosh_2018_J.Comput.Aided.Mol.Des_32_793 |
| Author(s) : Ghosh S , Jana K , Ganguly B |
| Ref : J Comput Aided Mol Des , 32 :793 , 2018 |
| Abstract : |
| PubMedSearch : Ghosh_2018_J.Comput.Aided.Mol.Des_32_793 |
| PubMedID: 29980922 |
| Title : Post-exposure treatment with the oxime RS194B rapidly reactivates and reverses advanced symptoms of lethal inhaled paraoxon in macaques - Rosenberg_2018_Toxicol.Lett_293_229 |
| Author(s) : Rosenberg YJ , Wang J , Ooms T , Rajendran N , Mao L , Jiang X , Lees J , Urban L , Romper J , Sepulveda Y , Shyong YJ , Taylor P |
| Ref : Toxicol Lett , 293 :229 , 2017 |
| Abstract : |
| PubMedSearch : Rosenberg_2018_Toxicol.Lett_293_229 |
| PubMedID: 29129799 |
| Title : Post-exposure treatment with the oxime RS194B rapidly reverses early and advanced symptoms in macaques exposed to sarin vapor - Rosenberg_2017_Chem.Biol.Interact_274_50 |
| Author(s) : Rosenberg YJ , Mao L , Jiang X , Lees J , Zhang L , Radic Z , Taylor P |
| Ref : Chemico-Biological Interactions , 274 :50 , 2017 |
| Abstract : |
| PubMedSearch : Rosenberg_2017_Chem.Biol.Interact_274_50 |
| PubMedID: 28693885 |
| Title : The biodistribution and pharmacokinetics of the oxime acetylcholinesterase reactivator RS194B in guinea pigs - Malfatti_2017_Chem.Biol.Interact_277_159 |
| Author(s) : Malfatti MA , Enright HA , Be NA , Kuhn EA , Hok S , McNerney MW , Lao V , Nguyen TH , Lightstone FC , Carpenter TS , Bennion BJ , Valdez CA |
| Ref : Chemico-Biological Interactions , 277 :159 , 2017 |
| Abstract : |
| PubMedSearch : Malfatti_2017_Chem.Biol.Interact_277_159 |
| PubMedID: 28941624 |
| Title : Planarian cholinesterase: in vitro characterization of an evolutionarily ancient enzyme to study organophosphorus pesticide toxicity and reactivation - Hagstrom_2017_Arch.Toxicol_91_2837 |
| Author(s) : Hagstrom D , Hirokawa H , Zhang L , Radic Z , Taylor P , Collins ES |
| Ref : Archives of Toxicology , 91 :2837 , 2016 |
| Abstract : |
| PubMedSearch : Hagstrom_2017_Arch.Toxicol_91_2837 |
| PubMedID: 27990564 |
| Gene_locus related to this paper: dugja-CHE1 , dugja-CHE2 |
| Title : Quaternary and tertiary aldoxime antidotes for organophosphate exposure in a zebrafish model system - Schmidt_2015_Toxicol.Appl.Pharmacol_284_197 |
| Author(s) : Schmidt HR , Radic Z , Taylor P , Fradinger EA |
| Ref : Toxicol Appl Pharmacol , 284 :197 , 2015 |
| Abstract : |
| PubMedSearch : Schmidt_2015_Toxicol.Appl.Pharmacol_284_197 |
| PubMedID: 25701203 |
| Title : A comprehensive evaluation of the efficacy of leading oxime therapies in guinea pigs exposed to organophosphorus chemical warfare agents or pesticides - Wilhelm_2014_Toxicol.Appl.Pharmacol_281_254 |
| Author(s) : Wilhelm CM , Snider TH , Babin MC , Jett DA , Platoff GE, Jr. , Yeung DT |
| Ref : Toxicol Appl Pharmacol , 281 :254 , 2014 |
| Abstract : |
| PubMedSearch : Wilhelm_2014_Toxicol.Appl.Pharmacol_281_254 |
| PubMedID: 25448441 |
| Title : Mechanism of interaction of novel uncharged, centrally active reactivators with OP-hAChE conjugates - Radic_2013_Chem.Biol.Interact_203_67 |
| Author(s) : Radic Z , Sit RK , Garcia E , Zhang LM , Zunec S , Kovarik Z , Amitai G , Fokin VV , Sharpless KB , Taylor P |
| Ref : Chemico-Biological Interactions , 203 :67 , 2013 |
| Abstract : |
| PubMedSearch : Radic_2013_Chem.Biol.Interact_203_67 |
| PubMedID: 22975155 |
| Title : Centrally acting oximes in reactivation of tabun-phosphoramidated AChE - Kovarik_2013_Chem.Biol.Interact_203_77 |
| Author(s) : Kovarik Z , Macek Hrvat N , Sit RK , Radic Z , Fokin VV , Sharpless KB , Taylor P |
| Ref : Chemico-Biological Interactions , 203 :77 , 2013 |
| Abstract : |
| PubMedSearch : Kovarik_2013_Chem.Biol.Interact_203_77 |
| PubMedID: 22960624 |
| Title : Refinement of structural leads for centrally acting oxime reactivators of phosphylated cholinesterases - Radic_2012_J.Biol.Chem_287_11798 |
| Author(s) : Radic Z , Sit RK , Kovarik Z , Zunec S , Garcia E , Zhang L , Amitai G , Green C , Radic B , Fokin VV , Sharpless KB , Taylor P |
| Ref : Journal of Biological Chemistry , 287 :11798 , 2012 |
| Abstract : |
| PubMedSearch : Radic_2012_J.Biol.Chem_287_11798 |
| PubMedID: 22343626 |
| Title : New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases - Sit_2011_J.Biol.Chem_286_19422 |
| Author(s) : Sit RK , Radic Z , Gerardi V , Zhang L , Garcia E , Katalinic M , Amitai G , Kovarik Z , Fokin VV , Sharpless KB , Taylor P |
| Ref : Journal of Biological Chemistry , 286 :19422 , 2011 |
| Abstract : |
| PubMedSearch : Sit_2011_J.Biol.Chem_286_19422 |
| PubMedID: 21464125 |