Avizafone

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27ClN4O3
Molecular Weight	430.928
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C(=O)CNC(=O)[C@@H](N)CCCCN)C1=CC=C(Cl)C=C1C(=O)C2=CC=CC=C2

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	430.928
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
Pharmacokinetic profile and quantitation of protection against soman poisoning by the antinicotinic compound MB327 in the guinea-pig.	2016-02-26	26325216
Human plasma-derived BuChE as a stoichiometric bioscavenger for treatment of nerve agent poisoning.	2013-03-25	22981459
Pharmacokinetic analysis of pralidoxime after its intramuscular injection alone or in combination with atropine-avizafone in healthy volunteers.	2010-12	20804498
Prediction of soman-induced cerebral damage by distortion product otoacoustic emissions.	2010-11-09	20816720
Bioavailability of diazepam after intramuscular injection of its water-soluble prodrug alone or with atropine-pralidoxime in healthy volunteers.	2009-08	19681868
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.	2008-10-15	18805073
Pyridinium oximes: rationale for their selection as causal antidotes against organophosphate poisonings and current solutions for auto-injectors.	2006-12	17265683
Protection against soman-induced neuropathology and respiratory failure: a comparison of the efficacy of diazepam and avizafone in guinea pig.	2006-08-01	16784801
LC-UV and LC-MS evaluation of stress degradation behaviour of avizafone.	2006-06-16	16644174
Efficacy of immediate and subsequent therapies against soman-induced seizures and lethality in rats.	2006-02	16445593
Comparative efficacy of diazepam and avizafone against sarin-induced neuropathology and respiratory failure in guinea pigs: influence of atropine dose.	2003-06-30	12767691

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:56 GMT 2025`
Record UNII	65NK71K78P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Avizafone

Official Name

English

RO 03-7355/000

Preferred Name

English

Ro-03-7355

Common Name

English

Avizafone [WHO-DD]

Common Name

English

Ro03-7355

Common 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 [INN]

Common Name

English

AVIZAFONE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197