MMB-4
General
Type : Oxime, Bisoxime, Bispyridinium
Chemical_Nomenclature : 1,1'-methylene bis[4-[(hydroxyimino)methyl] pyridinium]dibromide
Canonical SMILES : C1=CN(C=CC1=C[NH+]=O)CN2C=CC(=C[NH+]=O)C=C2.[Br-].[Br-]
InChI : InChI=1S\/C13H12N4O2.2BrH\/c18-14-9-12-1-5-16(6-2-12)11-17-7-3-13(4-8-17)10-15-19\;\;\/h1-10H,11H2\;2*1H
InChIKey : ZKQNRRLCBJUEBC-UHFFFAOYSA-N
Other name(s) : Methoxime || MMB4 || oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]pyridin-4-ylidene]methyl]azanium\;dibromide || N,N'-monomethylenebis(pyridiniumaldoxime) || CHEMBL451825 || MMB4 DMS
MW : 418.08
Formula : C13H14Br2N4O2
CAS_number :
PubChem : 5489503
UniChem : ZKQNRRLCBJUEBC-UHFFFAOYSA-N
References (16)
| 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 : Structural and dynamic effects of paraoxon binding to human acetylcholinesterase by X-ray crystallography and inelastic neutron scattering - Gerlits_2022_Structure_30_1538 |
| Author(s) : Gerlits O , Fajer M , Cheng X , Blumenthal DK , Radic Z , Kovalevsky A |
| Ref : Structure , 30 :1538 , 2022 |
| Abstract : |
| PubMedSearch : Gerlits_2022_Structure_30_1538 |
| PubMedID: 36265484 |
| Gene_locus related to this paper: human-ACHE |
| Title : Room temperature crystallography of human acetylcholinesterase bound to a substrate analogue 4K-TMA: Towards a neutron structure - Gerlits_2021_Curr.Res.Struct.Biol_3_206 |
| Author(s) : Gerlits O , Blakeley MP , Keen DA , Radic Z , Kovalevsky A |
| Ref : Current Research in Structural Biology , 3 :206 , 2021 |
| Abstract : |
| PubMedSearch : Gerlits_2021_Curr.Res.Struct.Biol_3_206 |
| PubMedID: 34541552 |
| Gene_locus related to this paper: human-ACHE |
| Title : The oximes HI-6 and MMB-4 fail to reactivate soman-inhibited human and guinea pig AChE: A kinetic in vitro study - Worek_2018_Toxicol.Lett_293_216 |
| Author(s) : Worek F , Thiermann H , Wille T |
| Ref : Toxicol Lett , 293 :216 , 2018 |
| Abstract : |
| PubMedSearch : Worek_2018_Toxicol.Lett_293_216 |
| PubMedID: 28993240 |
| Title : Evaluating the broad-spectrum efficacy of the acetylcholinesterase oximes reactivators MMB4 DMS, HLo-7 DMS, and 2-PAM Cl against phorate oxon, sarin, and VX in the Hartley guinea pig - Wilhelm_2018_Neurotoxicol_68_142 |
| Author(s) : Wilhelm CM , Snider TH , Babin MC , Platoff GE, Jr. , Jett DA , Yeung DT |
| Ref : Neurotoxicology , 68 :142 , 2018 |
| Abstract : |
| PubMedSearch : Wilhelm_2018_Neurotoxicol_68_142 |
| PubMedID: 30056178 |
| Title : Comparative Toxicokinetics of MMB4 DMS in Rats, Rabbits, Dogs, and Monkeys Following Single and Repeated Intramuscular Administration - Hong_2013_Int.J.Toxicol_32_38S |
| Author(s) : Hong SP , Gibbs ST , Kobs DJ , Hawk MA , Croutch CR , Osheroff MR , Johnson JD , Burback BL |
| Ref : Int J Toxicol , 32 :38S , 2013 |
| Abstract : |
| PubMedSearch : Hong_2013_Int.J.Toxicol_32_38S |
| PubMedID: 23929448 |
| Title : Evaluations of In Vitro Metabolism, Drug-Drug Interactions Mediated by Reversible and Time-Dependent Inhibition of CYPs, and Plasma Protein Binding of MMB4 DMS - Hong_2013_Int.J.Toxicol_32_75S |
| Author(s) : Hong SP , Lusiak BD , Burback BL , Johnson JD |
| Ref : Int J Toxicol , 32 :75S , 2013 |
| Abstract : |
| PubMedSearch : Hong_2013_Int.J.Toxicol_32_75S |
| PubMedID: 23929452 |
| Title : Aerosolized delivery of oxime MMB-4 in combination with atropine sulfate protects against soman exposure in guinea pigs - Perkins_2012_Inhal.Toxicol_24_539 |
| Author(s) : Perkins MW , Pierre Z , Sabnekar P , Sciuto AM , Song J , Soojhawon I , Oguntayo S , Doctor BP , Nambiar MP |
| Ref : Inhal Toxicol , 24 :539 , 2012 |
| Abstract : |
| PubMedSearch : Perkins_2012_Inhal.Toxicol_24_539 |
| PubMedID: 22860999 |
| Title : Reactivation of organophosphate-inhibited human, Cynomolgus monkey, swine and guinea pig acetylcholinesterase by MMB-4: a modified kinetic approach - Worek_2010_Toxicol.Appl.Pharmacol_249_231 |
| Author(s) : Worek F , Wille T , Aurbek N , Eyer P , Thiermann H |
| Ref : Toxicol Appl Pharmacol , 249 :231 , 2010 |
| Abstract : |
| PubMedSearch : Worek_2010_Toxicol.Appl.Pharmacol_249_231 |
| PubMedID: 20888357 |
| Title : A comparison of the efficacy of a new asymmetric bispyridinium oxime BI-6 with currently available oximes and H oximes against soman by in vitro and in vivo methods - Kassa_1999_Toxicology_132_111 |
| Author(s) : Kassa J , Cabal J |
| Ref : Toxicology , 132 :111 , 1999 |
| Abstract : |
| PubMedSearch : Kassa_1999_Toxicology_132_111 |
| PubMedID: 10433374 |
| Title : A comparison of the therapeutic efficacy of conventional and modern oximes against supralethal doses of highly toxic organophosphates in mice - Kassa_1998_Acta.Medica_41_19 |
| Author(s) : Kassa J |
| Ref : Acta Medica , 41 :19 , 1998 |
| Abstract : |
| PubMedSearch : Kassa_1998_Acta.Medica_41_19 |
| PubMedID: 9588068 |
| Title : [Comparison of the therapeutic effectiveness of selected cholinesterase reactivators with atropine in acute fosdrine poisoning in mice] - Kassa_1996_Ceska.Slov.Farm_45_31 |
| Author(s) : Kassa J , Bajgar J |
| Ref : Ceska a Slovenska Farmacie , 45 :31 , 1996 |
| Abstract : |
| PubMedSearch : Kassa_1996_Ceska.Slov.Farm_45_31 |
| PubMedID: 8620316 |
| Title : Comparison of several oximes on reactivation of soman-inhibited blood, brain and tissue cholinesterase activity in rats - Shih_1993_Arch.Toxicol_67_637 |
| Author(s) : Shih TM |
| Ref : Archives of Toxicology , 67 :637 , 1993 |
| Abstract : |
| PubMedSearch : Shih_1993_Arch.Toxicol_67_637 |
| PubMedID: 8311691 |
| Title : MMB-4 pharmacokinetics in rabbits after intravenous and intramuscular administration - |
| Author(s) : Woodard CL , Lukey BJ |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 19 :283 , 1991 |
| PubMedID: 1673416 |
| Title : Pharmacokinetics and pharmacodynamics of oximes in unanesthetized pigs - Stemler_1991_Fundam.Appl.Toxicol_16_548 |
| Author(s) : Stemler FW , Tezak-Reid TM , McCluskey MP , Kaminskis A , Corcoran KD , Shih ML , Stewart JR , Wade JV , Hayward IJ |
| Ref : Fundamental & Applied Toxicology , 16 :548 , 1991 |
| Abstract : |
| PubMedSearch : Stemler_1991_Fundam.Appl.Toxicol_16_548 |
| PubMedID: 1855625 |
| 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 |