Asoxime chloride

• CAS: 34433-31-3
• Catalog Number: ACM34433313
• Category: Main Products
• Molecular Weight: 359.21
• Molecular Formula: C₁₄H₁₆Cl₂N₄O₃
• Synonyms: (((4-(iminocarbonyl)pyridinio)methoxy)methyl)-2-((hydroxyimino)methyl)pyridi;4'-carbamoyl-2-formyl-1,1'-(oxydimethylene)di-pyridinium-dichloride-2-oxime;hi6;hi-6;hi-6dichloride;hj6;pyridinium,1-(((4-(aminocarbonyl)pyridinio)methoxy)methyl)-2-((hydroxyimino);pyridinium,4'-carbamoyl-2-formyl-1,1'-(oxydimethylene)di-,dichloride,2-oxi
• IUPAC Name: ASOXIME CHLORIDE
• Melting Point: 145-147°C
• Appearance: Off-White Solid
• Exact Mass: 358.06000

Case Study

Asoxime Chloride (HI-6) as a Nerve Agent Antidote: Safety and Oxidative Stress Assessment in Canine Model

Pohanka, Miroslav, et al. environmental toxicology and pharmacology 32.1 (2011): 75-81.

Asoxime chloride (HI-6) is a potent oxime reactivator used to counteract organophosphate nerve agent poisoning by restoring acetylcholinesterase (AChE) activity. This study evaluated its adverse effects, pharmacokinetics, and oxidative stress impact in Beagle dogs at therapeutic (11.4 mg/kg) and tenfold therapeutic (114 mg/kg) intramuscular doses.
Experimental Protocol: Blood samples were collected before and at 30, 120, and 240 min post-administration. Markers included thiobarbituric acid reactive substances (TBARS), ferric reducing antioxidant power (FRAP), glutathione levels, serum biochemistry, and HI-6 residual plasma concentration via HPLC.
Performance Evaluation: HI-6 peaked at 30 min (4.21 mg/L for therapeutic, 27.04 mg/L for tenfold dose). At therapeutic dose, plasma FRAP increased significantly at 120 min, while blood TBARS elevated at 30 min then returned to baseline. Tenfold dose caused sustained TBARS elevation across all time points, with FRAP also increased at 120-240 min. Serum biochemistry revealed significant hyperglycemia (p≤0.01) at 240 min for both doses, and elevated BUN, CPK, and triglycerides (p≤0.05) only at tenfold dose. No significant changes in GSH, GSSG, or liver enzymes were observed.
Conclusion: HI-6 at therapeutic dose is relatively safe but induces mild, transient oxidative stress and hyperglycemia. Tenfold dose triggers pronounced oxidative stress and metabolic disorders, supporting cautious use in overdose scenarios.

Asoxime Chloride (HI-6) as an Immunomodulatory Adjuvant via IL-2 Upregulation

Pohanka, Miroslav. Neuroendocrinology Letters 35 (2014): 2.

Asoxime chloride (HI-6), a well-known oxime reactivator for organophosphate poisoning, also exhibits immunomodulatory properties by selectively increasing interleukin-2 (IL-2) levels, suggesting its potential as a vaccine adjuvant.
Experimental Protocol: BALB/c mice received intramuscular injections of saline, HI-6 (0.1-100 mg/kg), keyhole limpet hemocyanin (KLH, 1 mg/kg), or their combinations. After 21 days, plasma levels of IL-1β, IL-2, IL-4, and IL-6 were quantified by ELISA.
Performance Evaluation: No significant changes were observed in IL-1β, IL-4, or IL-6 across all groups. However, HI-6 at 10 and 100 mg/kg combined with KLH significantly elevated IL-2 levels (46.7±5.5 and 58.7±9.7 pg/mL, respectively) compared to controls (39.9±1.3 pg/mL, p<0.01). HI-6 alone without KLH did not alter IL-2. The effect is attributed to enhanced acetylcholine availability via AChE inhibition, activating the cholinergic anti-inflammatory pathway.
Conclusion: HI-6 upregulates IL-2 in an antigen-dependent manner, supporting its role as an adjuvant to boost weak immune responses, e.g., in vaccination or anti-pathogen therapies.

Custom Q&A

What is the molecular formula of asoxime chloride?

The molecular formula of asoxime chloride is C14H16Cl2N4O3.

What are the synonyms of asoxime chloride?

The synonyms of asoxime chloride are asoxime dichloride and 1-[[2-(Hydroxyiminomethyl)pyridin-1-ium-1-yl]methoxymethyl]pyridin-1-ium-4-carboxamide;dichloride.

What is the molecular weight of asoxime chloride?

The molecular weight of asoxime chloride is 359.2 g/mol.

When was asoxime chloride created?

Asoxime chloride was created on August 8, 2005.

What is the IUPAC name of asoxime chloride?

The IUPAC name of asoxime chloride is 1-[[2-(hydroxyiminomethyl)pyridin-1-ium-1-yl]methoxymethyl]pyridin-1-ium-4-carboxamide;dichloride.

What is the InChIKey of asoxime chloride?

The InChIKey of asoxime chloride is QELSIJXWEROXOE-UHFFFAOYSA-N.

How many hydrogen bond donor counts does asoxime chloride have?

Asoxime chloride has 2 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does asoxime chloride have?

Asoxime chloride has 6 hydrogen bond acceptor counts.

What is the topological polar surface area of asoxime chloride?

The topological polar surface area of asoxime chloride is 92.7 Ų.

Is asoxime chloride a canonicalized compound?

Yes, asoxime chloride is a canonicalized compound.