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MedKoo Cat#: 573289 | Name: Asoxime chloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Asoxime, also known as HI-6, is an oxime reactivator used for counteracting intoxication by nerve agents. It is able to reactivate acetylcholinesterase (AChE) inhibited by cytotoxic nerve agents such as sarin or soman. AChE is a primary target of organophosphates, which inactivate it by reacting with the active center serine. This prevents the hydrolysis of acetylcholine at peripheral and central synapses. Asoxime reactivates phosphorylated AChE that has been inhibited by exposure to cytotoxic nerve agents.

Chemical Structure

Asoxime chloride
Asoxime chloride
CAS#34433-31-3 (chloride)

Theoretical Analysis

MedKoo Cat#: 573289

Name: Asoxime chloride

CAS#: 34433-31-3 (chloride)

Chemical Formula: C14H16Cl2N4O3

Exact Mass: 358.0599

Molecular Weight: 359.21

Elemental Analysis: C, 46.81; H, 4.49; Cl, 19.74; N, 15.60; O, 13.36

Price and Availability

Size Price Availability Quantity
10mg USD 400.00 2 Weeks
25mg USD 700.00 2 Weeks
50mg USD 1,000.00 2 Weeks
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Related CAS #
34433-31-3 (chloride) 144252-71-1 (mesylate) 82504-20-9 (chloride hydrate)
Synonym
Asoxime chloride, HI-6, HI 6, HI6, HI-6 Dichloride, HJ 6, Transant, WR 249655; WR-249655; WR249655; Asoxime dichloride
IUPAC/Chemical Name
(E)-1-(((4-carbamoylpyridin-1-ium-1-yl)methoxy)methyl)-2-((hydroxyimino)methyl)pyridin-1-ium chloride
InChi Key
QELSIJXWEROXOE-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O/N=C/C1=[N+](COC[N+]2=CC=C(C(N)=O)C=C2)C=CC=C1.[Cl-].[Cl-]
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Certificate of Analysis
View CoA: current batch, Lot#C22M11C02
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 359.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Andrýs R, Klusoňová A, Lísa M, Kassa J, Karasová JŽ. Effect of Oxime Encapsulation on Acetylcholinesterase Reactivation: Pharmacokinetic Study of the Asoxime-Cucurbit[7]uril Complex in Mice Using Hydrophilic Interaction Liquid Chromatography-Mass Spectrometry. Mol Pharm. 2021 Jun 7;18(6):2416-2427. doi: 10.1021/acs.molpharmaceut.1c00257. Epub 2021 May 21. PMID: 34019427. 2: Pohanka M, Novotny L, Zdarova-Karasova J, Bandouchova H, Zemek F, Hrabinova M, Misik J, Kuca K, Bajgar J, Zitka O, Cernei N, Kizek R, Pikula J. Asoxime (HI-6) impact on dogs after one and tenfold therapeutic doses: assessment of adverse effects, distribution, and oxidative stress. Environ Toxicol Pharmacol. 2011 Jul;32(1):75-81. doi: 10.1016/j.etap.2011.03.014. Epub 2011 Apr 1. PMID: 21787733. 3: Antonijevic E, Kotur-Stevuljevic J, Musilek K, Kosvancova A, Kuca K, Djukic- Cosic D, Spasojevic-Kalimanovska V, Antonijevic B. Effect of six oximes on acutely anticholinesterase inhibitor-induced oxidative stress in rat plasma and brain. Arch Toxicol. 2018 Feb;92(2):745-757. doi: 10.1007/s00204-017-2101-z. Epub 2017 Nov 2. PMID: 29098328. 4: Rousseaux CG, Dua AK. Pharmacology of HI-6, an H-series oxime. Can J Physiol Pharmacol. 1989 Oct;67(10):1183-9. doi: 10.1139/y89-188. PMID: 2692793. 5: Pohanka M. Alpha7 nicotinic acetylcholine receptor is a target in pharmacology and toxicology. Int J Mol Sci. 2012;13(2):2219-2238. doi: 10.3390/ijms13022219. Epub 2012 Feb 17. PMID: 22408449; PMCID: PMC3292018. 6: Myhrer T, Aas P. Choice of approaches in developing novel medical countermeasures for nerve agent poisoning. Neurotoxicology. 2014 Sep;44:27-38. doi: 10.1016/j.neuro.2014.04.011. Epub 2014 May 9. PMID: 24820435. 7: Bajgar J. Optimal choice of acetylcholinesterase reactivators for antidotal treatment of nerve agent intoxication. Acta Medica (Hradec Kralove). 2010;53(4):207-11. doi: 10.14712/18059694.2016.78. PMID: 21400978. 8: Lundy PM, Hamilton MG, Sawyer TW, Mikler J. Comparative protective effects of HI-6 and MMB-4 against organophosphorous nerve agent poisoning. Toxicology. 2011 Jul 29;285(3):90-6. doi: 10.1016/j.tox.2011.04.006. Epub 2011 Apr 15. PMID: 21524678. 9: van Helden HP, Busker RW, Melchers BP, Bruijnzeel PL. Pharmacological effects of oximes: how relevant are they? Arch Toxicol. 1996;70(12):779-86. doi: 10.1007/s002040050340. PMID: 8911635. 10: Pohanka M, Pejchal J, Horackova S, Kuca K, Bandouchova H, Damkova V, Pikula J. Modulation of ionising radiation generated oxidative stress by HI-6 (asoxime) in a laboratory rat model. Neuro Endocrinol Lett. 2010;31 Suppl 2:62-8. PMID: 21187825. 11: Luo C, Saxena A, Ashani Y, Leader H, Radić Z, Taylor P, Doctor BP. Role of edrophonium in prevention of the re-inhibition of acetylcholinesterase by phosphorylated oxime. Chem Biol Interact. 1999 May 14;119-120:129-35. doi: 10.1016/s0009-2797(99)00021-6. PMID: 10421446. 12: Lundy PM, Raveh L, Amitai G. Development of the bisquaternary oxime HI-6 toward clinical use in the treatment of organophosphate nerve agent poisoning. Toxicol Rev. 2006;25(4):231-43. doi: 10.2165/00139709-200625040-00004. PMID: 17288495. 13: Stojiljković MP, Škrbić R, Jokanović M, Bokonjić D, Kilibarda V, Vulović M. Prophylactic potential of memantine against soman poisoning in rats. Toxicology. 2019 Mar 15;416:62-74. doi: 10.1016/j.tox.2019.01.012. Epub 2019 Jan 22. PMID: 30682440. 14: Joosen MJA, Vester SM, Hamelink J, Klaassen SD, van den Berg RM. Increasing nerve agent treatment efficacy by P-glycoprotein inhibition. Chem Biol Interact. 2016 Nov 25;259(Pt B):115-121. doi: 10.1016/j.cbi.2016.06.012. Epub 2016 Jun 7. PMID: 27287416. 15: Wei Z, Liu YQ, Wang YA, Li WH, Zhou XB, Zhao J, Huang CQ, Li XZ, Liu J, Zheng ZB, Li S. Novel nonquaternary reactivators showing reactivation efficiency for soman-inhibited human acetylcholinesterase. Toxicol Lett. 2016 Mar 30;246:1-6. doi: 10.1016/j.toxlet.2016.01.015. Epub 2016 Jan 22. PMID: 26809136. 16: Shih T, Whalley CE, Valdes JJ. A comparison of cholinergic effects of HI-6 and pralidoxime-2-chloride (2-PAM) in soman poisoning. Toxicol Lett. 1991 Feb;55(2):131-47. doi: 10.1016/0378-4274(91)90128-s. PMID: 1998202. 17: Li Y, Huang L, Zhang Z, Huang J, Xing H, Wang L, Sui X, Luo Y, Wang Y, Yang J. An in vitro nerve agent brain poisoning transwell model for convenient and accurate antidote evaluation. Toxicol In Vitro. 2023 Apr;88:105541. doi: 10.1016/j.tiv.2022.105541. Epub 2022 Dec 23. PMID: 36572320. 18: Hepnarova V, Muckova L, Ring A, Pejchal J, Herman D, Misik J, Hrabinova M, Jun D, Soukup O. Pharmacological and toxicological in vitro and in vivo effect of higher doses of oxime reactivators. Toxicol Appl Pharmacol. 2019 Nov 15;383:114776. doi: 10.1016/j.taap.2019.114776. Epub 2019 Oct 17. PMID: 31629733. 19: Yudin MA, Subbotina SN, Bykov VN, Chepur SV, Nikiforov AS. Prospects of using benzodiazepines in complex therapy of poisonings with anticholinesterase agents. Bull Exp Biol Med. 2013 Jul;155(3):354-9. doi: 10.1007/s10517-013-2152-y. PMID: 24137602. 20: Maček Hrvat N, Žunec S, Taylor P, Radić Z, Kovarik Z. HI-6 assisted catalytic scavenging of VX by acetylcholinesterase choline binding site mutants. Chem Biol Interact. 2016 Nov 25;259(Pt B):148-153. doi: 10.1016/j.cbi.2016.04.023. Epub 2016 Apr 12. PMID: 27083141; PMCID: PMC5061595.