ASOXIME CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16N4O3.2Cl
Molecular Weight	359.208
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].[Cl-].NC(=O)C1=CC=[N+](COC[N+]2=CC=CC=C2\C=N\O)C=C1

InChI

InChIKey=QELSIJXWEROXOE-UHFFFAOYSA-N

InChI=1S/C14H14N4O3.2ClH/c15-14(19)12-4-7-17(8-5-12)10-21-11-18-6-2-1-3-13(18)9-16-20;;/h1-9H,10-11H2,(H-,15,19);2*1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H15N4O3
Molecular Weight	287.2939
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28684009	Inhibitor 8297		667.8 µM [IC50]

PubMed

Title	Date	PubMed
Spontaneous and oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates.	1988	3240095
Comparison of oxime-initiated reactivation of organophosphorous-inhibited acetylcholinesterase in brains of avian embryos.	2000 Jan 14	10681099
Active site mutant acetylcholinesterase interactions with 2-PAM, HI-6, and DDVP.	2006 Apr 14	16598855
Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators.	2008 Oct 19	18804659
Comparison of oxime reactivation and aging of nerve agent-inhibited monkey and human acetylcholinesterases.	2008 Sep 25	18555982
A comparison of reactivating efficacy of newly developed oximes (K074, K075) and currently available oximes (obidoxime, HI-6) in soman, cyclosarin and tabun-poisoned rats.	2008 Sep 25	18547554
New bispyridinium oximes: in vitro and in vivo evaluation of their biological efficiency in soman and tabun poisoning.	2008 Sep 25	18547553
Comparison of the oxime-induced reactivation of rhesus monkey, swine and guinea pig erythrocyte acetylcholinesterase following inhibition by sarin or paraoxon, using a perfusion model for the real-time determination of membrane-bound acetylcholinesterase activity.	2009 Apr 28	19428926
Effect of acetylcholinesterase oxime-type reactivators K-48 and HI-6 on human liver microsomal cytochromes P450 in vitro.	2009 Aug 14	19539805
In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048.	2009 Jun	18825528
Interaction of pentylsarin analogues with human acetylcholinesterase: a kinetic study.	2009 Jun 1	19429253
Comparative study of oxime-induced reactivation of erythrocyte and muscle AChE from different animal species following inhibition by sarin or paraoxon.	2010 May 4	20156534
Prediction of soman-induced cerebral damage by distortion product otoacoustic emissions.	2010 Nov 9	20816720
Comparison of human and guinea pig acetylcholinesterase sequences and rates of oxime-assisted reactivation.	2010 Sep 6	20433814
Interactions of pyridinium oximes with acetylcholinesterase.	2010 Sep 6	20417629
Interaction kinetics of oximes with native, phosphylated and aged human acetylcholinesterase.	2010 Sep 6	20412789
In vivo reactivation by oximes of inhibited blood, brain and peripheral tissue cholinesterase activity following exposure to nerve agents in guinea pigs.	2010 Sep 6	20223229
Tabun-inhibited rat tissue and blood cholinesterases and their reactivation with the combination of trimedoxime and HI-6 in vivo.	2010 Sep 6	20167212
Kinetic analysis of interactions of different sarin and tabun analogues with human acetylcholinesterase and oximes: is there a structure-activity relationship?	2010 Sep 6	20105433
Mechanism for potent reactivation ability of H oximes analyzed by reactivation kinetic studies with cholinesterases from different species.	2010 Sep 6	20096273
In vitro ability of currently available oximes to reactivate organophosphate pesticide-inhibited human acetylcholinesterase and butyrylcholinesterase.	2011	21673941
Gene expression and phosphoprotein profile of certain key neuronal signaling proteins following soman intoxication.	2011 Dec 18	21971501
Kinetic analysis of interactions of paraoxon and oximes with human, Rhesus monkey, swine, rabbit, rat and guinea pig acetylcholinesterase.	2011 Jan 15	20971170
Effect of different buffers on kinetic properties of human acetylcholinesterase and the interaction with organophosphates and oximes.	2011 Mar	20669006
In vitro effects of acetylcholinesterase reactivators on monoamine oxidase activity.	2011 Mar 5	21195145
Amidine-oximes: reactivators for organophosphate exposure.	2011 May 12	21438612
Reactivation of organophosphate-inhibited human acetylcholinesterase by isonitrosoacetone (MINA): a kinetic analysis.	2011 Nov 15	21930118
A comparison of the reactivating and therapeutic efficacy of chosen combinations of oximes with individual oximes against VX in rats and mice.	2011 Oct	22013137
Restoration of nerve agent inhibited muscle force production in human intercostal muscle strips with HI 6.	2011 Sep 25	21803135
Immobilization of Russian VX skin depots by localized cooling: implications for decontamination and medical countermeasures.	2011 Sep 25	21704135
Increasing oxime efficacy by blood-brain barrier modulation.	2011 Sep 25	21600273
Comparative kinetics of organophosphates and oximes with erythrocyte, muscle and brain acetylcholinesterase.	2012 Mar 7	22230262
Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility.	2013 Dec 15	23959147
In vitro investigation of efficacy of new reactivators on OPC inhibited rat brain acetylcholinesterase.	2013 Mar 25	23220589
Syntheses and in vitro evaluations of uncharged reactivators for human acetylcholinesterase inhibited by organophosphorus nerve agents.	2013 Mar 25	23111374
A common mechanism for resistance to oxime reactivation of acetylcholinesterase inhibited by organophosphorus compounds.	2013 Mar 25	22982773
Human plasma-derived BuChE as a stoichiometric bioscavenger for treatment of nerve agent poisoning.	2013 Mar 25	22981459
Reactions of methylphosphonic difluoride with human acetylcholinesterase and oximes--Possible therapeutic implications.	2014 Nov 18	25240274
Effect of reversible ligands on oxime-induced reactivation of sarin- and cyclosarin-inhibited human acetylcholinesterase.	2015 Feb 3	25522658
Probing the role of amino acids in oxime-mediated reactivation of nerve agent-inhibited human acetylcholinesterase.	2015 Mar	25451328
Pharmacokinetic profile and quantitation of protection against soman poisoning by the antinicotinic compound MB327 in the guinea-pig.	2016 Feb 26	26325216

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:21:58 GMT 2023` Edited by `admin` on `Fri Dec 15 19:21:58 GMT 2023`
Record UNII	HUV88P6SJS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASOXIME CHLORIDE

Common Name

English

1-(((4-(AMINOCARBONYL)PYRIDINIO)METHOXY)METHYL)-2-((HYDROXYIMINO)METHYL)PYRIDINIUM CHLORIDE (1:2)

Systematic Name

English

4'-CARBAMOYL-2-FORMYL-1,1'-(OXYDIMETHYLENE)DIPYRIDINIUM CHLORIDE 2-OXIME

Common Name

English

TRANSANT

Brand Name

English

ASOXIME CHLORIDE [MI]

Common Name

English

1-(2-HYDROXYIMINOMETHYL-1-PYRIDINIO)-3-(4-CARBAMOYL-1-PYRIDINIO)-2-OXAPROPANE DICHLORIDE

Systematic Name

English

ASOXIME CHLORIDE [MART.]

Common Name

English

HI-6

Code

English

Code System Code Type Description

FDA UNII

HUV88P6SJS