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=C(\C=N\O)C=CC=C2)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	C14H15N4O3
Molecular Weight	287.2939
Charge	1
Count

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

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28684009	Inhibitor 8504		667.8 µM [IC50]

PubMed

Title	Date	PubMed
Pharmacokinetic profile and quantitation of protection against soman poisoning by the antinicotinic compound MB327 in the guinea-pig.	2016-02-26	26325216
Probing the role of amino acids in oxime-mediated reactivation of nerve agent-inhibited human acetylcholinesterase.	2015-03	25451328
Effect of reversible ligands on oxime-induced reactivation of sarin- and cyclosarin-inhibited human acetylcholinesterase.	2015-02-03	25522658
Reactions of methylphosphonic difluoride with human acetylcholinesterase and oximes--Possible therapeutic implications.	2014-11-18	25240274
Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility.	2013-12-15	23959147
In vitro investigation of efficacy of new reactivators on OPC inhibited rat brain acetylcholinesterase.	2013-03-25	23220589
Syntheses and in vitro evaluations of uncharged reactivators for human acetylcholinesterase inhibited by organophosphorus nerve agents.	2013-03-25	23111374
A common mechanism for resistance to oxime reactivation of acetylcholinesterase inhibited by organophosphorus compounds.	2013-03-25	22982773
Human plasma-derived BuChE as a stoichiometric bioscavenger for treatment of nerve agent poisoning.	2013-03-25	22981459
Comparative kinetics of organophosphates and oximes with erythrocyte, muscle and brain acetylcholinesterase.	2012-03-07	22230262
Gene expression and phosphoprotein profile of certain key neuronal signaling proteins following soman intoxication.	2011-12-18	21971501
Reactivation of organophosphate-inhibited human acetylcholinesterase by isonitrosoacetone (MINA): a kinetic analysis.	2011-11-15	21930118
A comparison of the reactivating and therapeutic efficacy of chosen combinations of oximes with individual oximes against VX in rats and mice.	2011-10	22013137
Restoration of nerve agent inhibited muscle force production in human intercostal muscle strips with HI 6.	2011-09-25	21803135
Immobilization of Russian VX skin depots by localized cooling: implications for decontamination and medical countermeasures.	2011-09-25	21704135
Increasing oxime efficacy by blood-brain barrier modulation.	2011-09-25	21600273
Amidine-oximes: reactivators for organophosphate exposure.	2011-05-12	21438612
In vitro effects of acetylcholinesterase reactivators on monoamine oxidase activity.	2011-03-05	21195145
Effect of different buffers on kinetic properties of human acetylcholinesterase and the interaction with organophosphates and oximes.	2011-03	20669006
Kinetic analysis of interactions of paraoxon and oximes with human, Rhesus monkey, swine, rabbit, rat and guinea pig acetylcholinesterase.	2011-01-15	20971170
In vitro ability of currently available oximes to reactivate organophosphate pesticide-inhibited human acetylcholinesterase and butyrylcholinesterase.	2011	21673941
Prediction of soman-induced cerebral damage by distortion product otoacoustic emissions.	2010-11-09	20816720
Comparison of human and guinea pig acetylcholinesterase sequences and rates of oxime-assisted reactivation.	2010-09-06	20433814
Interactions of pyridinium oximes with acetylcholinesterase.	2010-09-06	20417629
Interaction kinetics of oximes with native, phosphylated and aged human acetylcholinesterase.	2010-09-06	20412789
In vivo reactivation by oximes of inhibited blood, brain and peripheral tissue cholinesterase activity following exposure to nerve agents in guinea pigs.	2010-09-06	20223229
Tabun-inhibited rat tissue and blood cholinesterases and their reactivation with the combination of trimedoxime and HI-6 in vivo.	2010-09-06	20167212
Kinetic analysis of interactions of different sarin and tabun analogues with human acetylcholinesterase and oximes: is there a structure-activity relationship?	2010-09-06	20105433
Mechanism for potent reactivation ability of H oximes analyzed by reactivation kinetic studies with cholinesterases from different species.	2010-09-06	20096273
Comparative study of oxime-induced reactivation of erythrocyte and muscle AChE from different animal species following inhibition by sarin or paraoxon.	2010-05-04	20156534
Effect of acetylcholinesterase oxime-type reactivators K-48 and HI-6 on human liver microsomal cytochromes P450 in vitro.	2009-08-14	19539805
Interaction of pentylsarin analogues with human acetylcholinesterase: a kinetic study.	2009-06-01	19429253
In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048.	2009-06	18825528
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.	2009-04-28	19428926
Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators.	2008-10-19	18804659
Comparison of oxime reactivation and aging of nerve agent-inhibited monkey and human acetylcholinesterases.	2008-09-25	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.	2008-09-25	18547554
New bispyridinium oximes: in vitro and in vivo evaluation of their biological efficiency in soman and tabun poisoning.	2008-09-25	18547553
Active site mutant acetylcholinesterase interactions with 2-PAM, HI-6, and DDVP.	2006-04-14	16598855
Comparison of oxime-initiated reactivation of organophosphorous-inhibited acetylcholinesterase in brains of avian embryos.	2000-01-14	10681099
Reactivation by various oximes of human erythrocyte acetylcholinesterase inhibited by different organophosphorus compounds.	1996	8783813
Spontaneous and oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates.	1988	3240095

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:43:57 GMT 2025` Edited by `admin` on `Mon Mar 31 19:43:57 GMT 2025`
Record UNII	HUV88P6SJS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASOXIME CHLORIDE

Common Name

English

TRANSANT

Preferred 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

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