Trimedoxime

General

Type : Oxime, Bisoxime, Bispyridinium

Chemical_Nomenclature : oxo-[[1-[3-[4-(oxoazaniumylmethylidene)pyridin-1-yl]propyl]pyridin-4-ylidene]methyl]azanium\;dibromide

Canonical SMILES : C1=CN(C=CC1=C[NH+]=O)CCCN2C=CC(=C[NH+]=O)C=C2.[Br-].[Br-]

InChI : InChI=1S\/C15H16N4O2.2BrH\/c20-16-12-14-2-8-18(9-3-14)6-1-7-19-10-4-15(5-11-19)13-17-21\;\;\/h2-5,8-13H,1,6-7H2\;2*1H

InChIKey : JHZHWVQTOXIXIV-UHFFFAOYSA-N,    LJYGXPCCGGSATE-UHFFFAOYSA-P

Other name(s) : TMB-4  ||  TMB4  ||  Trimedoxime  ||  Dipyroxime  ||  Dipiroxim  ||  Trimedoxime N  ||  Dipiroxim dibromide  ||  BRN 1552160  ||  6736-02-3  ||  Pyridinium, 1,1'-(1,3-propanediyl)bis(4-(hydroxyimino)methyl-  ||  oxo-[[1-[3-[4-(oxoazaniumylmethylidene)pyridin-1-yl]propyl]pyridin-4-ylidene]methyl]azanium\;dibromide


MW : 446.137

Formula : C15H18Br2N4O2

CAS_number : 56-97-3

PubChem : 5489619,    5359236

UniChem : JHZHWVQTOXIXIV-UHFFFAOYSA-N,    LJYGXPCCGGSATE-UHFFFAOYSA-P

Wikipedia : Trimedoxime_bromide

Target

Structure : No structure

Families : No family

References (46)

Title : The reactivation kinetic analysis, molecular docking, and dynamics of oximes against three V-type nerve agents inhibited four human cholinesterases - Li_2024_Chem.Biol.Interact__111061
Author(s) : Li K , Liu Y , Li Q , Guo L , Xie J
Ref : Chemico-Biological Interactions , :111061 , 2024
Abstract :
PubMedSearch : Li_2024_Chem.Biol.Interact__111061
PubMedID: 38763347

Title : Understanding the Interaction Modes and Reactivity of Trimedoxime toward MmAChE Inhibited by Nerve Agents: Theoretical and Experimental Aspects - de Castro_2020_Int.J.Mol.Sci_21_
Author(s) : de Castro AA , Polisel DA , Pereira BTL , da Cunha EFF , Kuca K , Nepovimova E , Ramalho TC
Ref : Int J Mol Sci , 21 : , 2020
Abstract :
PubMedSearch : de Castro_2020_Int.J.Mol.Sci_21_
PubMedID: 32899591

Title : The Evaluation of the Reactivating and Neuroprotective Efficacy of Two Newly Prepared Bispyridinium Oximes (K305, K307) in Tabun-Poisoned Rats-A Comparison with Trimedoxime and the Oxime K203 - Kassa_2017_Molecules_22_
Author(s) : Kassa J , Misik J , Hatlapatkova J , Karasova JZ , Sepsova V , Caisberger F , Pejchal J
Ref : Molecules , 22 : , 2017
Abstract :
PubMedSearch : Kassa_2017_Molecules_22_
PubMedID: 28696367

Title : A comparison of neuroprotective efficacy of two novel reactivators of acetylcholinesterase called K920 and K923 with the oxime K203 and trimedoxime in tabun-poisoned rats - Kassa_2017_Toxicol.Mech.Methods__1
Author(s) : Kassa J , Misik J , Hatlapatkova J , Karasova JZ
Ref : Toxicol Mech Methods , :1 , 2017
Abstract :
PubMedSearch : Kassa_2017_Toxicol.Mech.Methods__1
PubMedID: 28043192

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 : 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 : A physiologically based pharmacokinetic model for the oxime TMB-4(Trimedoxime): simulation of rodent and human data - Sterner_2013_Arch.Toxicol_87_661
Author(s) : Sterner TR , Ruark CD , Covington TR , Yu KO , Gearhart JM
Ref : Archives of Toxicology , 87 :661 , 2013
Abstract :
PubMedSearch : Sterner_2013_Arch.Toxicol_87_661
PubMedID: 23314320

Title : Pharmacokinetic study of two acetylcholinesterase reactivators, trimedoxime and newly synthesized oxime K027, in rat plasma - Karasova_2013_J.Appl.Toxicol_33_18
Author(s) : Karasova JZ , Chladek J , Hroch M , Josef F , Hnidkova D , Kuca K
Ref : J Appl Toxicol , 33 :18 , 2013
Abstract :
PubMedSearch : Karasova_2013_J.Appl.Toxicol_33_18
PubMedID: 21717485

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 : 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 : Partition of bispyridinium oximes (trimedoxime and K074) administered in therapeutic doses into different parts of the rat brain - Karasova_2011_J.Pharm.Biomed.Anal_54_1082
Author(s) : Karasova JZ , Zemek F , Bajgar J , Vasatova M , Prochazka P , Novotny L , Kuca K
Ref : J Pharm Biomed Anal , 54 :1082 , 2011
Abstract :
PubMedSearch : Karasova_2011_J.Pharm.Biomed.Anal_54_1082
PubMedID: 21146949

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 : Tabun-inhibited rat tissue and blood cholinesterases and their reactivation with the combination of trimedoxime and HI-6 in vivo - Bajgar_2010_Chem.Biol.Interact_187_287
Author(s) : Bajgar J , Karasova JZ , Kassa J , Cabal J , Fusek J , Blaha V , Tesarova S
Ref : Chemico-Biological Interactions , 187 :287 , 2010
Abstract :
PubMedSearch : Bajgar_2010_Chem.Biol.Interact_187_287
PubMedID: 20167212

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 : 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 : A comparison of the therapeutic and reactivating efficacy of newly developed oximes (K117, K127) and currently available oximes (obidoxime, trimedoxime, HI-6) in tabun-poisoned rats and mice - Kassa_2008_Drug.Chem.Toxicol_31_371
Author(s) : Kassa J , Karasova J , Musilek K , Kuca K , Jung YS
Ref : Drug & Chemical Toxicology , 31 :371 , 2008
Abstract :
PubMedSearch : Kassa_2008_Drug.Chem.Toxicol_31_371
PubMedID: 18622871

Title : Evaluation of potency of known oximes (pralidoxime, trimedoxime, HI-6, methoxime, obidoxime) to in vitro reactivate acetylcholinesterase inhibited by pesticides (chlorpyrifos and methylchlorpyrifos) and nerve agent (Russian VX) - Musilek_2007_Acta.Medica.(Hradec.Kralove)_50_203
Author(s) : Musilek K , Kuca K , Jun D
Ref : Acta Medica (Hradec Kralove) , 50 :203 , 2007
Abstract :
PubMedSearch : Musilek_2007_Acta.Medica.(Hradec.Kralove)_50_203
PubMedID: 18254274

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 : Hydrolysis of acetylthiocholine iodide and reactivation of phoxim-inhibited acetylcholinesterase by pralidoxime chloride, obidoxime chloride and trimedoxime - Zhang_2007_Arch.Toxicol_81_785
Author(s) : Zhang YH , Miyata T , Wu ZJ , Wu G , Xie LH
Ref : Archives of Toxicology , 81 :785 , 2007
Abstract :
PubMedSearch : Zhang_2007_Arch.Toxicol_81_785
PubMedID: 17534602

Title : In vitro potency of H oximes (HI-6, HLo-7), the oxime BI-6, and currently used oximes (pralidoxime, obidoxime, trimedoxime) to reactivate nerve agent-inhibited rat brain acetylcholinesterase - Kuca_2006_J.Toxicol.Environ.Health.A_69_1431
Author(s) : Kuca K , Cabal J , Kassa J , Jun D , Hrabinova M
Ref : J Toxicol Environ Health A , 69 :1431 , 2006
Abstract :
PubMedSearch : Kuca_2006_J.Toxicol.Environ.Health.A_69_1431
PubMedID: 16766478

Title : Efficacy of trimedoxime in mice poisoned with dichlorvos, heptenophos or monocrotophos - Antonijevic_2005_Basic.Clin.Pharmacol.Toxicol_96_111
Author(s) : Antonijevic B , Bokonjic D , Stojiljkovic MP , Kilibarda V , Milovanovic ZA , Nedeljkovic M , Maksimovic M
Ref : Basic Clin Pharmacol Toxicol , 96 :111 , 2005
Abstract :
PubMedSearch : Antonijevic_2005_Basic.Clin.Pharmacol.Toxicol_96_111
PubMedID: 15679473

Title : A comparison of the potency of trimedoxime and other currently available oximes to reactivate tabun-inhibited acetylcholinesterase and eliminate acute toxic effects of tabun - Kassa_2005_Biomed.Pap.Med.Fac.Univ.Palacky.Olomouc.Czech.Repub_149_419
Author(s) : Kassa J , Kuca K , Cabal J
Ref : Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub , 149 :419 , 2005
Abstract :
PubMedSearch : Kassa_2005_Biomed.Pap.Med.Fac.Univ.Palacky.Olomouc.Czech.Repub_149_419
PubMedID: 16601802

Title : Stability of mono- and bisbenzyloxime ethers of the acetylcholinesterase reactivator TMB-4(Trimedoxime) - Inkmann_1997_Pharmazie_52_764
Author(s) : Inkmann E , Holzgrabe U , Hesse KF
Ref : Pharmazie , 52 :764 , 1997
Abstract :
PubMedSearch : Inkmann_1997_Pharmazie_52_764
PubMedID: 9362091

Title : Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates - Jokanovic_1996_Toxicol.Lett_85_35
Author(s) : Jokanovic M , Maksimovic M , Kilibarda V , Jovanovic D , Savic D
Ref : Toxicology Letters , 85 :35 , 1996
Abstract :
PubMedSearch : Jokanovic_1996_Toxicol.Lett_85_35
PubMedID: 8619258

Title : Oxime effects on the rate constants of carbamylation and decarbamylation of acetylcholinesterase for pyridostigmine, physostigmine and insecticidal carbamates - Dawson_1995_Neurochem.Int_26_643
Author(s) : Dawson RM
Ref : Neurochem Int , 26 :643 , 1995
Abstract :
PubMedSearch : Dawson_1995_Neurochem.Int_26_643
PubMedID: 7670367

Title : Disposition and metabolism of acetylcholinesterase reactivators 2PAM-I, TMB4 and R665 in rats submitted to organophosphate poisoning - Garrigue_1991_Xenobiotica_21_583
Author(s) : Garrigue H , Maurizis JC , Madelmont JC , Nicolas C , Meyniel JM , Louvel A , Demerseman P , Sentenac-Roumanou H , Veyre A
Ref : Xenobiotica , 21 :583 , 1991
Abstract :
PubMedSearch : Garrigue_1991_Xenobiotica_21_583
PubMedID: 1949891

Title : [A comparative study of the therapeutic and reactivating activities of alloxime and dipyroxime in acute poisoning of animals by organophosphate pesticides] - Loboda_1990_Farmakol.Toksikol_53_64
Author(s) : Loboda Iu I
Ref : Farmakologiia i Toksikologiia , 53 :64 , 1990
Abstract :
PubMedSearch : Loboda_1990_Farmakol.Toksikol_53_64
PubMedID: 2328807

Title : Stability studies of bis(pyridiniumaldoxime) reactivators of organophosphate-inhibited acetylcholinesterase - Lin_1986_J.Pharmaceutical.Sci_75_797
Author(s) : Lin AJ , Klayman DL
Ref : Journal of Pharmaceutical Sciences , 75 :797 , 1986
Abstract :
PubMedSearch : Lin_1986_J.Pharmaceutical.Sci_75_797
PubMedID: 3772753

Title : Clinical observation and comparison of the effectiveness of several oxime cholinesterase reactivators - Xue_1985_Scand.J.Work.Environ.Health_4_46
Author(s) : Xue SZ , Ding XJ , Ding Y
Ref : Scandinavian Journal of Work, Environment & Health , 4 :46 , 1985
Abstract :
PubMedSearch : Xue_1985_Scand.J.Work.Environ.Health_4_46
PubMedID: 3914075

Title : [Trial of cholinesterase reactivators as proserine antagonists]. [Russian] - Prozorovskii_1983_Biull.Eksp.Biol.Med_96_66
Author(s) : Prozorovskii VB , Khramova EA , Ardab'eva TV
Ref : Biulleten Eksperimentalnoi Biologii i Meditsiny , 96 :66 , 1983
Abstract :
PubMedSearch : Prozorovskii_1983_Biull.Eksp.Biol.Med_96_66
PubMedID: 6354300

Title : [Effect of the organophosphorus compound neguvon on the dopamine content in the rat brain]. [Bulgarian] - Dishovski_1981_Eksp.Med.Morfol_20_62
Author(s) : Dishovski K , Panova I , Uzunov P
Ref : Eksperimentalna Meditsina i Morfologiia , 20 :62 , 1981
Abstract :
PubMedSearch : Dishovski_1981_Eksp.Med.Morfol_20_62
PubMedID: 7250022

Title : [Changes in the transverse striated musculature during treatment with the pesticide, Neguvon, and TMB-4(Trimedoxime) reactivator]. [Bulgarian] - Dzhirkolova_1979_Eksp.Med.Morfol_18_31
Author(s) : Dzhirkolova T , Dishovski K , Rusev G
Ref : Eksperimentalna Meditsina i Morfologiia , 18 :31 , 1979
Abstract :
PubMedSearch : Dzhirkolova_1979_Eksp.Med.Morfol_18_31
PubMedID: 436709

Title : [Therapy of domestic animals affected by alkylphosphates] - Benes_1979_Vet.Med_24_623
Author(s) : Benes J , Hrusovsky J , Proksova M
Ref : Vet Med , 24 :623 , 1979
Abstract :
PubMedSearch : Benes_1979_Vet.Med_24_623
PubMedID: 117593

Title : [Effect of arpenal on the EMG-potentials of the anterior tibial muscle in cats during acute phosdrine poisoning] - Mashkova_1976_Eksp.Med.Morfol_15_237
Author(s) : Mashkova D
Ref : Eksperimentalna Meditsina i Morfologii , 15 :237 , 1976
Abstract :
PubMedSearch : Mashkova_1976_Eksp.Med.Morfol_15_237
PubMedID: 1017412

Title : [Therapy of organophosphate poisoning in animals] - Benes_1976_Vet.Med_21_343
Author(s) : Benes J , Proksova M , Hrusovsky J
Ref : Vet Med , 21 :343 , 1976
Abstract :
PubMedSearch : Benes_1976_Vet.Med_21_343
PubMedID: 826002

Title : [Antidotal effect of TMB-4(Trimedoxime) compos. Spofa in sheep intoxicated with O-ethyl S-(2-dimethylaminoethyl) methyl phosphonothioate]. [Czech] - Benes_1976_Vet.Med_21_237
Author(s) : Benes J , Proksova M , Hrusovsky J
Ref : Veterinarni Medicina , 21 :237 , 1976
Abstract :
PubMedSearch : Benes_1976_Vet.Med_21_237
PubMedID: 824781

Title : [Effect of some reactivators on cholinesterase activity in the chromodacryorrhea test in rats]. [Bulgarian] - Naneva_1976_Vet.Med.Nauki_13_81
Author(s) : Naneva E
Ref : Veterinarno Meditsinski Nauki , 13 :81 , 1976
Abstract :
PubMedSearch : Naneva_1976_Vet.Med.Nauki_13_81
PubMedID: 799866

Title : [Reactivating effect of trimedoxime and obidoxime on cholinesterases inhibited in the heart and intercostal muscles of the rat during acute poisoning with O-ethyl-S-(dimethylaminethyl)-methylthiophosphonate. (A histochemical study)]. [Czech] -
Author(s) : Picha B
Ref : Sb Ved Pr Lek Fak Karlovy Univerzity Hradci Kralove , 17 :195 , 1974
PubMedID: 4620479

Title : Changes in cholinesterase activity in white rats, after several injections of TMB-4(Trimedoxime) and atropine, following treatment with parathion -
Author(s) : Boyadjiev S
Ref : Folia Medica , 16 :281 , 1974
PubMedID: 4219941

Title : [The resorption rate of TMB-4(Trimedoxime) Cl2 antidote after intramuscular administration by injection, syringe and autoinjector in control and poisoned animals] -
Author(s) : Vojvodic V , Boskovic B , Vojvodic M
Ref : Vojnosanit Pregl , 30 :239 , 1973
PubMedID: 4768015

Title : [Electron microscopic studies of the synaptic structure of the n. caudatus in the rat brain during experimental dimethyl dichlorvinyl phosphate poisoning treated with TMB-4(Trimedoxime)]. [Bulgarian] -
Author(s) : Kotev G , Dishtovski K
Ref : Eksperimentalna Meditsina i Morfologiia , 11 :141 , 1972
PubMedID: 4667628

Title : Blood concentrations of N,N' -trimethylenebis (pyridinium-4-aldoxime) (TMB-4(Trimedoxime)) and NN'-oxydimethylenebis (pyridinium-4-aldoxime) (toxogenin) after intravenous and intramuscular administration in the dos -
Author(s) : Milosevic MP , Voivodic V , Terzic M
Ref : Biochemical Pharmacology , 16 :2435 , 1967
PubMedID: 6075402

Title : The reactivatin,g and antidotal actions of N,N' -trimethylenebis (pyridinium-4-aldoxime) (TMB-4(Trimedoxime)) and N,N-oxydimethylenebis (pyridinium-4-aldoxime) (toxogenin) with particular reference to their effect on phosphorylated acetylcholinesterase in brain -
Author(s) : Hobbiger F , Voivodi V
Ref : Biochemical Pharmacology , 15 :1677 , 1966
PubMedID:

Title : Relation between the chemical structure and the acute toxicity in the series of alkyl-alkoxy derivatives of p-nitrophenyl phosphoric acid and the protective effects of PAM-2, TMB-4(Trimedoxime) and atropine -
Author(s) : Vojvodic V , Likar D , Binenfeld Z , Stevanovic M
Ref : Acta Med. Iugoslav , 15 :463 , 1961
PubMedID:

Title : Protection against lethal phosphamidon poisoning by N,N'-trimethylene bis (4-hydroximino methylpyridinium bromide) (TMB-4(Trimedoxime)) -
Author(s) : Milosevic MP , Terzic M , Vojvodic V
Ref : Archives Internationales de Pharmacodynamie et de Therapie , 132 :180 , 1961
PubMedID:

Title : Chemotherapeutic effectiveness of 1,1'-tri-methylene bis(4-formylpyridinium bromide) dioxime (TMB-4(Trimedoxime)) in experimental anti-cholinesterase poisoning -
Author(s) : Bay E , Krop S , Yates LF
Ref : Proceedings of the Society for Experimental Biology & Medicine , 98 :107 , 1958
PubMedID: 13554557