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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 of AVIZAFONE

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

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

PubMed

TitleDatePubMed
Comparative efficacy of diazepam and avizafone against sarin-induced neuropathology and respiratory failure in guinea pigs: influence of atropine dose.
2003 Jun 30
Protection against soman-induced neuropathology and respiratory failure: a comparison of the efficacy of diazepam and avizafone in guinea pig.
2006 Aug 1
Pyridinium oximes: rationale for their selection as causal antidotes against organophosphate poisonings and current solutions for auto-injectors.
2006 Dec
Efficacy of immediate and subsequent therapies against soman-induced seizures and lethality in rats.
2006 Feb
LC-UV and LC-MS evaluation of stress degradation behaviour of avizafone.
2006 Jun 16
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
Bioavailability of diazepam after intramuscular injection of its water-soluble prodrug alone or with atropine-pralidoxime in healthy volunteers.
2009 Aug
Pharmacokinetic analysis of pralidoxime after its intramuscular injection alone or in combination with atropine-avizafone in healthy volunteers.
2010 Dec
Prediction of soman-induced cerebral damage by distortion product otoacoustic emissions.
2010 Nov 9
Human plasma-derived BuChE as a stoichiometric bioscavenger for treatment of nerve agent poisoning.
2013 Mar 25
Pharmacokinetic profile and quantitation of protection against soman poisoning by the antinicotinic compound MB327 in the guinea-pig.
2016 Feb 26
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
  • Download
Name Type Language
AVIZAFONE
INN   MART.  
INN  
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
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
NCI_THESAURUS C29756
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
Code System Code Type Description
FDA UNII
65NK71K78P
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
EVMPD
SUB05616MIG
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL2103985
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
MESH
C065249
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
PUBCHEM
71968
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
EPA CompTox
65617-86-9
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
WIKIPEDIA
AVIZAFONE
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
CAS
65617-86-9
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
INN
6723
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
NCI_THESAURUS
C72708
Created by admin on Sat Jun 26 08:38:47 UTC 2021 , Edited by admin on Sat Jun 26 08:38:47 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG