Avizafone

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 ;
PubChem CID	71968;
ChemSpider	64974 ;
UNII	65NK71K78P;
ChEMBL	ChEMBL2103985 ;
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 ; Key:LTKOVYBBGBGKTA-SFHVURJKSA-N ;
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Avizafone^[1] (Pro-Diazepam) is a water-soluble prodrug of the benzodiazepine derivative diazepam. It can be administered intramuscularly.

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]

References

^ GB 1517164
^ 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.
^ 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.
^ 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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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)