Asoxime chloride

Chemical compound From Wikipedia, the free encyclopedia

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

ATC code
  • none
Legal status
  • Experimental
Quick facts Clinical data, Routes ofadministration ...
Asoxime chloride
Clinical data
Routes of
administration
Intramuscular injection
ATC code
  • none
Legal status
Legal status
  • Experimental
Identifiers
  • 4-carbamoyl-1-[({2-[(E)-(hydroxyimino)methyl]pyridinium-1-yl}methoxy)methyl]pyridinium dichloride
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H16Cl2N4O3
Molar mass359.21 g·mol−1
3D model (JSmol)
  • C1=CC=[N+](C(=C1)/C=N/O)COC[N+]2=CC=C(C=C2)C(=O)N.[Cl-].[Cl-]
  • 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
  • Key:QELSIJXWEROXOE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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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].

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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