Asoxime chloride

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Asoxime chloride
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Clinical data
Routes of
administration		Intramuscular injection
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  • none
Legal status
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  • Experimental
Identifiers
  • 4-carbamoyl-1-[({2-[(E)-(hydroxyimino)methyl]pyridinium-1-yl}methoxy)methyl]pyridinium dichloride
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Chemical and physical data
FormulaC14H16Cl2N4O3
Molar mass359.21 g·mol−1
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  • 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 checkY
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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].

File:Position of key groups in Hagedorn Oximes using HI-6 as support.jpg
Position of key groups in Hagedorn Oxime HI-6 (Positions 2 and 4 with respect to the pyridine ring derive most potency, while the amide group in Position two (red) decreases toxicity of HI-6

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Franz Worek, Peter A. Eyer (2007). Chemical Warfare Agents: Toxicology and Treatment. Chapter 15: Wiley. p. 305-329. doi:10.1002/9780470060032. ISBN 9780470060032.{{cite book}}: CS1 maint: location (link)
  4. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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.

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