Avizafone

Summary

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
  • (2S)-2,6-diamino-N-{[(2-benzoyl-4-chlorophenyl)methylcarbamoyl]methyl}hexanamide
CAS Number
  • 65617-86-9 checkY
PubChem CID
  • 71968
ChemSpider
  • 64974 checkY
UNII
  • 65NK71K78P
ChEMBL
  • ChEMBL2103985 ☒N
CompTox Dashboard (EPA)
  • DTXSID90215868 Edit this at Wikidata
Chemical and physical data
FormulaC22H27ClN4O3
Molar mass430.93 g·mol−1
3D model (JSmol)
  • Interactive image
  • Clc1cc(c(N(C(=O)CNC(=O)[C@@H](N)CCCCN)C)cc1)C(=O)c2ccccc2
  • 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 checkY
  • Key:LTKOVYBBGBGKTA-SFHVURJKSA-N checkY
 ☒NcheckY (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 edit

References edit

  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.