Asoxime chloride

Asoxime chloride

Clinical data
Routes of administration	Intramuscular injection
ATC code	none
Legal status
Legal status	Experimental
Identifiers
IUPAC name 4-carbamoyl-1-[({2-[(E)-(hydroxyimino)methyl]pyridinium-1-yl}methoxy)methyl]pyridinium dichloride
CAS Number	34433-31-3  N
PubChem CID	5484128
ChemSpider	13004322  Y
UNII	HUV88P6SJS
ChEMBL	ChEMBL33051  Y
CompTox Dashboard (EPA)	DTXSID101029616
Chemical and physical data
Formula	C14H16Cl2N4O3
Molar mass	359.21 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=[N+](C(=C1)/C=N/O)COC[N+]2=CC=C(C=C2)C(=O)N.[Cl-].[Cl-]
InChI InChI=1S/C14H14N4O3.2ClH/c15-14(19)12-4-7-17(8-5-12)10-21-11-18-6-2-1-3-13(18)9-16-20;;/h1-9H,10-11H2,(H-,15,19);2*1H Y Key:QELSIJXWEROXOE-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

Asoxime chloride, or more commonly HI-6, is a Hagedorn oxime used in the treatment of organophosphate poisoning. ^[1]

Discovery

HI-6 was developed in the 1968 in Ilse Hagedorn ^[2] 's lab at the University of Freiburg in then West Germany as a potent antidote for poisoning by organophosphorus nerve agents. ^[3] The compound was created in response to limitations of earlier oxime antidotes, which were effective against some nerve agents but failed to protect against others such as soman. ^[4]

Structure

Much line pralidoxime, asoxime and other oximes created in the Hagedorn lab (i.e. LüH-6, HLö-7) are pyridine oximes, sharing the same structural feature of a byspyridinium nucleus. Position 2 and 4 on one of the pyridine rings is essential for pharmacological activity, as is position 4 on the second ring for both efficacy and toxic effects alike. Amidation on the second ring at position 4 is essential for reducing toxicity of the derivative compounds ^[5] .

See also

• Obidoxime
• Pralidoxime

References

1. Cochran R, Kalisiak J, Küçükkilinç T, Radic Z, Garcia E, Zhang L, et al. (August 2011). "Oxime-assisted acetylcholinesterase catalytic scavengers of organophosphates that resist aging". The Journal of Biological Chemistry. 286 (34): 29718–24. doi: 10.1074/jbc.M111.264739 . PMC   3191013 . PMID   21730071.
2. Peter Eyer (20 April 2007). "In memory of Ilse Hagedorn". Toxicology. 233 (1–3). Elsevier: 3–7. doi: 10.1016/j.tox.2006.09.014 .
3. Franz Worek, Peter A. Eyer (2007). Chemical Warfare Agents: Toxicology and Treatment. Chapter 15: Wiley. p. 305-329. doi: 10.1002/9780470060032 . ISBN   9780470060032.
4. K Schoene, H Oldiges (1970). "Pyridinium- und Imidazoliumsalze als Antidote gegenüber Soman- und Paraoxonvergiftungen bei Mäusen". Archiv für Toxikologie. 26. Springer Nature: 293–305. doi:10.1007/BF00577721.
5. Peter A. Lockwood, John G. Clement (1982). "HI-6, an oxime which is an effective antidote of soman poisoning: A structure-activity study". Toxicology and Applied Pharmacology. 64 (1). Elsevier: 140–146. doi:10.1016/0041-008X(82)90332-5.