TRIMEDOXIME BROMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18N4O2.2Br
Molecular Weight	446.137
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].[Br-].O\N=C\C1=CC=[N+](CCC[N+]2=CC=C(C=C2)\C=N\O)C=C1

InChI

InChIKey=JHZHWVQTOXIXIV-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H16N4O2
Molecular Weight	284.3131
Charge	0
Count

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

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24295433 | Morton, I.K., Hall, J.M. (2012) Concise Dictionary of Pharmacological Agents, page 281, retrieved from: https://books.google.ru/books?id=tsjrCAAAQBAJ | Atta-ur-Rahman et al. (2016) Frontiers in Medicinal Chemistry, page 187, retrieved from: https://books.google.ca/books?id=AxpHDgAAQBAJ

Trimedoxime is the only one of the major bispyridinium oxime with a propylene linked between the two pyridinium rings. Trimedoxime is an oxime cholinesterase (AChE) reactivator. It was shown that trimedoxime is a more potent reactivator of the DFP-inhibited AChE than pralidoxime and a better reactivator than obidoxime in the case of the tabun-inhibited enzyme. It can be used parenterally as an antidote adjunct to atropine in treating human or animal (organophosphate group) anticholinesterase pesticide toxicity. Trimedoxime was the first oxime that was efficient in the treatment of animals intoxicated with tabun. It could also protect animals poisoned with sarin or VX, but not the ones intoxicated with soman.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: P22303\|\|\|Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16766478	Activator 1430

PubMed

Title	Date	PubMed
[Effect of a new cholinesterase reactivator, diethixime, on the central nervous system].	1977 Jan	856330
[Noncholinesterase component in the molecular mechanism of action of the cholinesterase reactivator dipyroxime].	1982 Jun	7115940
Feeding behavior and brain acetylcholinesterase activity in bream (Abramis brama L.) as affected by DDVP, an organophosphorus insecticide.	1992 Nov	1363306
Comparison of oxime-initiated reactivation of organophosphorous-inhibited acetylcholinesterase in brains of avian embryos.	2000 Jan 14	10681099
Efficacy of trimedoxime in mice poisoned with dichlorvos, heptenophos or monocrotophos.	2005 Feb	15679473
Potency of several oximes to reactivate human acetylcholinesterase and butyrylcholinesterase inhibited by paraoxon in vitro.	2008 Sep 25	18617161
In vitro reactivating effects of standard and newly developed oximes on malaoxon-inhibited mouse brain acetylcholinesterase.	2010 Sep	20406208
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
The antidotal efficacy of the bispyridinium oximes K027 and TMB-4 against tabun poisoning in mice.	2010 Sep 6	20138854
In vitro ability of currently available oximes to reactivate organophosphate pesticide-inhibited human acetylcholinesterase and butyrylcholinesterase.	2011	21673941
An acetylcholinesterase biosensor for determination of low concentrations of Paraoxon and Dichlorvos.	2011 Dec 15	21600321
In vitro effects of acetylcholinesterase reactivators on monoamine oxidase activity.	2011 Mar 5	21195145
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
In vitro investigation of efficacy of new reactivators on OPC inhibited rat brain acetylcholinesterase.	2013 Mar 25	23220589
Testing of novel brain-penetrating oxime reactivators of acetylcholinesterase inhibited by nerve agent surrogates.	2013 Mar 25	23123249
In vitro reactivation kinetics of paraoxon- and DFP-inhibited electric eel AChE using mono- and bis-pyridinium oximes.	2014 Feb	24065055
Interactions between xylene-linked carbamoyl bis-pyridinium mono-oximes and organophosphates inhibited-AChE: a kinetic study.	2014 Feb 28	24345352

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:00:49 UTC 2023` Edited by `admin` on `Fri Dec 15 15:00:49 UTC 2023`
Record UNII	ED0GXI9825
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEDOXIME BROMIDE

Official Name

English

TMB-4

Code

English

trimedoxime bromide [INN]

Common Name

English

Trimedoxime bromide [WHO-DD]

Common Name

English

C-434

Code

English

1,1'-TRIMETHYLENEBIS(4-FORMYLPYRIDINIUM BROMIDE)DIOXIME

Systematic Name

English

TRIMEDOXIME BROMIDE [MART.]

Common Name

English

NSC-148341

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66880