AVIZAFONE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27ClN4O3
Molecular Weight	430.9286
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(c1ccc(cc1C(=O)c2ccccc2)Cl)C(=O)CN=C([C@]([H])(CCCCN)N)O

InChI

InChIKey=LTKOVYBBGBGKTA-SFHVURJKSA-N

InChI=1S/C22H27ClN4O3/c1-27(20(28)14-26-22(30)18(25)9-5-6-12-24)19-11-10-16(23)13-17(19)21(29)15-7-3-2-4-8-15/h2-4,7-8,10-11,13,18H,5-6,9,12,14,24-25H2,1H3,(H,26,30)/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H27ClN4O3
Molecular Weight	430.9286
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20804498 | https://www.ncbi.nlm.nih.gov/pubmed/30837282 | https://www.ncbi.nlm.nih.gov/pubmed/19681868 | https://www.ncbi.nlm.nih.gov/pubmed/8164892 |

Avizafone is a water-soluble peptide prodrug of diazepam that is hydrolyzed by an aminopeptidase to liberate lysine and diazepam Avizafone was developed by the French military to terminate seizures caused by battlefield nerve agents. Diazepam has a faster entry to the general circulation and achieved higher maximum concentration after injection of prodrug than after the parent drug and this is extremely valuable in nerve agents poisoning conditions.

Approval Year

PubMed

Title	Date	PubMed
Comparative efficacy of diazepam and avizafone against sarin-induced neuropathology and respiratory failure in guinea pigs: influence of atropine dose.	2003 Jun 30	12767691
Protection against soman-induced neuropathology and respiratory failure: a comparison of the efficacy of diazepam and avizafone in guinea pig.	2006 Aug 1	16784801
Pyridinium oximes: rationale for their selection as causal antidotes against organophosphate poisonings and current solutions for auto-injectors.	2006 Dec	17265683
Efficacy of immediate and subsequent therapies against soman-induced seizures and lethality in rats.	2006 Feb	16445593
LC-UV and LC-MS evaluation of stress degradation behaviour of avizafone.	2006 Jun 16	16644174
High-performance liquid chromatography coupled with electrospray tandem mass spectrometry (LC/MS/MS) method for the simultaneous determination of diazepam, atropine and pralidoxime in human plasma.	2008 Oct 15	18805073
Bioavailability of diazepam after intramuscular injection of its water-soluble prodrug alone or with atropine-pralidoxime in healthy volunteers.	2009 Aug	19681868
Pharmacokinetic analysis of pralidoxime after its intramuscular injection alone or in combination with atropine-avizafone in healthy volunteers.	2010 Dec	20804498
Prediction of soman-induced cerebral damage by distortion product otoacoustic emissions.	2010 Nov 9	20816720
Human plasma-derived BuChE as a stoichiometric bioscavenger for treatment of nerve agent poisoning.	2013 Mar 25	22981459
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 `Sat Jun 26 08:38:47 UTC 2021` Edited by `admin` on `Sat Jun 26 08:38:47 UTC 2021`
Record UNII	65NK71K78P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AVIZAFONE

Official Name

English

2'-BENZOYL-4'-CHLORO-2-((S)-2,6-DIAMINOHEXANAMIDO)-N-METHYLACETANILIDE

Systematic Name

English

RO-037355000

Code

English

RO-03-7355/000

Code

English

AVIZAFONE [WHO-DD]

Common Name

English

AVIZAFONE [INN]

Common Name

English

AVIZAFONE [MART.]

Common Name

English

RO 03-7355/000

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197