Avizafone

Avizafone[1] (Pro-Diazepam) is a water-soluble prodrug of the benzodiazepine derivative diazepam. It can be administered intramuscularly.

Avizafone

Clinical data
Routes of administration	Intramuscular injection
ATC code	none
Identifiers
IUPAC name (2S)-2,6-diamino-N-{[(2-benzoyl-4-chlorophenyl)methylcarbamoyl]methyl}hexanamide
CAS Number	65617-86-9^Y
PubChem CID	71968
ChemSpider	64974^Y
UNII	65NK71K78P
ChEMBL	ChEMBL2103985^N
CompTox Dashboard (EPA)	DTXSID90215868
Chemical and physical data
Formula	C22H27ClN4O3
Molar mass	430.93 g·mol^−1
3D model (JSmol)	Interactive image
SMILES Clc1cc(c(N(C(=O)CNC(=O)[C@@H](N)CCCCN)C)cc1)C(=O)c2ccccc2
InChI 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^Y Key:LTKOVYBBGBGKTA-SFHVURJKSA-N^Y
^NY (what is this?)  (verify)

Avizafone is metabolised by enzymes in the blood to form the active drug diazepam. It is used mainly as an antidote to poisoning with organophosphate nerve agents.[2][3][4]

See also

• Alprazolam triazolobenzophenone
• Rilmazafone

References

1. GB Patent 1517164
2. Karlsson B, Lindgren B, Millquist E, Sandberg M, Sellstrom A. On the use of diazepam and pro-diazepam (2-benzoyl-4-chloro-N-methyl-N-lysylglycin anilide), as adjunct antidotes in the treatment of organophosphorus intoxication in the guinea-pig. Journal of Pharmacy and Pharmacology. 1990 Apr;42(4):247-51.
3. Lallement G, Renault F, Baubichon D, Peoc'h M, Burckhart MF, Galonnier M, Clarencon D, Jourdil N. Compared efficacy of diazepam or avizafone to prevent soman-induced electroencephalographic disturbances and neuropathology in primates: relationship to plasmatic benzodiazepine pharmacokinetics. Archives of Toxicology. 2000 Oct;74(8):480-6.
4. Taysse L, Calvet JH, Buee J, Christin D, Delamanche S, Breton P. Comparative efficacy of diazepam and avizafone against sarin-induced neuropathology and respiratory failure in guinea pigs: influence of atropine dose. Toxicology. 2003 Jun 30;188(2-3):197-209.