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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H27ClN4O3
Molar mass430.93 g·mol−1
3D model (JSmol)
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

References
  1. GB 1517164
  2. Karlsson B, Lindgren B, Millquist E, Sandberg M, Sellström A (April 1990). "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". The Journal of Pharmacy and Pharmacology. 42 (4): 247–51. doi:10.1111/j.2042-7158.1990.tb05401.x. PMID 1974291. S2CID 32369013.
  3. Lallement G, Renault F, Baubichon D, Peoc'h M, Burckhart MF, Galonnier M, et al. (October 2000). "Compared efficacy of diazepam or avizafone to prevent soman-induced electroencephalographic disturbances and neuropathology in primates: relationship to plasmatic benzodiazepine pharmacokinetics". Archives of Toxicology. 74 (8): 480–6. doi:10.1007/s002040000146. PMID 11097386. S2CID 22292597.
  4. Taysse L, Calvet JH, Buée J, Christin D, Delamanche S, Breton P (June 2003). "Comparative efficacy of diazepam and avizafone against sarin-induced neuropathology and respiratory failure in guinea pigs: influence of atropine dose". Toxicology. 188 (2–3): 197–209. doi:10.1016/s0300-483x(03)00086-6. PMID 12767691.
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