TRIMEDOXIME CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18N4O2.2Cl
Molecular Weight	357.235
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=UTVALPBGSAUYNR-UHFFFAOYSA-N

InChI=1S/C15H16N4O2.2ClH/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	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	C15H16N4O2
Molecular Weight	284.3131
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
Potency of several oximes to reactivate human acetylcholinesterase and butyrylcholinesterase inhibited by paraoxon in vitro.	2008 Sep 25	18617161
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 investigation of efficacy of new reactivators on OPC inhibited rat brain acetylcholinesterase.	2013 Mar 25	23220589
In vitro reactivation kinetics of paraoxon- and DFP-inhibited electric eel AChE using mono- and bis-pyridinium oximes.	2014 Feb	24065055

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:51:20 GMT 2023` Edited by `admin` on `Sat Dec 16 10:51:20 GMT 2023`
Record UNII	32YLZ3021T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMEDOXIME CHLORIDE

Common Name

English

PYRIDINIUM, 1,1'-(1,3-PROPANEDIYL)BIS(4-((HYDROXYIMINO)METHYL)-, CHLORIDE (1:2)

Systematic Name

English

NSC-76060

Code

English

TRIMEDOXIME DICHLORIDE

Common Name

English

Code System Code Type Description

PUBCHEM

107427

Created by admin on Sat Dec 16 10:51:20 GMT 2023 , Edited by admin on Sat Dec 16 10:51:20 GMT 2023

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NSC

76060

Created by admin on Sat Dec 16 10:51:20 GMT 2023 , Edited by admin on Sat Dec 16 10:51:20 GMT 2023

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CAS

3613-82-9

Created by admin on Sat Dec 16 10:51:20 GMT 2023 , Edited by admin on Sat Dec 16 10:51:20 GMT 2023

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FDA UNII

32YLZ3021T

Created by admin on Sat Dec 16 10:51:20 GMT 2023 , Edited by admin on Sat Dec 16 10:51:20 GMT 2023

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Related Record Type Details


					53E8JHT760

TRIMEDOXIME

ACTIVE MOIETY