Obidoxime chloride

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MedKoo CAT#: 527959

CAS#: 114-90-9 (Cl)

Description: Obidoxime chloride is a cholinesterase reactivator occurring in two interchangeable isomeric forms, syn and anti.

Chemical Structure

Obidoxime chloride
CAS# 114-90-9 (Cl)

Theoretical Analysis

MedKoo Cat#: 527959
Name: Obidoxime chloride
CAS#: 114-90-9 (Cl)
Chemical Formula: C14H16Cl2N4O3
Exact Mass: 358.0599
Molecular Weight: 359.207
Elemental Analysis: C, 46.81; H, 4.49; Cl, 19.74; N, 15.60; O, 13.36

Price and Availability

Size Price Availability Quantity
250.0mg USD 300.0 2 Weeks
500.0mg USD 550.0 2 Weeks
1.0g USD 900.0 2 Weeks
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Related CAS #: 2337-82-8 (Br)   73840-43-4 (sulfate)   4605-73-6 (iodide)   114-90-9 (Cl)  

Synonym: Obidoxime chloride; Toxogonin

IUPAC/Chemical Name: 1,1'-(Oxydimethylene)bis(4-formylpyridinium) dichloride dioxime


InChi Code: InChI=1S/C14H14N4O3.2ClH/c19-15-9-13-1-5-17(6-2-13)11-21-12-18-7-3-14(4-8-18)10-16-20;;/h1-10H,11-12H2;2*1H

SMILES Code: O/N=C/C1=CC=[N+](COC[N+]2=CC=C(/C=N/O)C=C2)C=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

Preparing Stock Solutions

The following data is based on the product molecular weight 359.207 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

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1: Joosen MJA, Klaassen SD, Verheij E, van Groningen T, Cornelissen AS, Skiadopoulos MH, Cochrane L, Shearer JD. Efficacy of atropine sulfate/obidoxime chloride co-formulation against sarin exposure in guinea pigs. Chem Biol Interact. 2018 Sep 12;296:34-42. doi: 10.1016/j.cbi.2018.09.004. [Epub ahead of print] PubMed PMID: 30217478.

2: Kuca K, Jun D, Junova L, Musilek K, Hrabinova M, da Silva JAV, Ramalho TC, Valko M, Wu Q, Nepovimova E, França TCC. Synthesis, Biological Evaluation, and Docking Studies of Novel Bisquaternary Aldoxime Reactivators on Acetylcholinesterase and Butyrylcholinesterase Inhibited by Paraoxon. Molecules. 2018 May 7;23(5). pii: E1103. doi: 10.3390/molecules23051103. PubMed PMID: 29735900.

3: Moyer RA, McGarry KG Jr, Babin MC, Platoff GE Jr, Jett DA, Yeung DT. Kinetic analysis of oxime-assisted reactivation of human, Guinea pig, and rat acetylcholinesterase inhibited by the organophosphorus pesticide metabolite phorate oxon (PHO). Pestic Biochem Physiol. 2018 Feb;145:93-99. doi: 10.1016/j.pestbp.2018.01.009. Epub 2018 Jan 31. PubMed PMID: 29482737; PubMed Central PMCID: PMC5830159.

4: Krishnan JKS, Figueiredo TH, Moffett JR, Arun P, Appu AP, Puthillathu N, Braga MF, Flagg T, Namboodiri AM. Brief isoflurane administration as a post-exposure treatment for organophosphate poisoning. Neurotoxicology. 2017 Dec;63:84-89. doi: 10.1016/j.neuro.2017.09.009. Epub 2017 Sep 20. PubMed PMID: 28939237.

5: Pathak AK, Bandyopadhyay T. Unbinding of fluorinated oxime drug from the AChE gorge in polarizable water: a well-tempered metadynamics study. Phys Chem Chem Phys. 2017 Feb 15;19(7):5560-5569. doi: 10.1039/c6cp08518k. PubMed PMID: 28165084.

6: Karade HN, Raviraju G, Acharya BN, Valiveti AK, Bhalerao U, Acharya J. Synthesis and in vitro reactivation study of isonicotinamide derivatives of 2-(hydroxyimino)-N-(pyridin-3-yl)acetamide as reactivators of Sarin and VX inhibited human acetylcholinesterase (hAChE). Bioorg Med Chem. 2016 Sep 15;24(18):4171-4176. doi: 10.1016/j.bmc.2016.07.005. Epub 2016 Jul 6. PubMed PMID: 27450532.

7: Snider TH, Babin MC, Jett DA, Platoff GE Jr, Yeung DT. Toxicity and median effective doses of oxime therapies against percutaneous organophosphorus pesticide and nerve agent challenges in the Hartley guinea pig. J Toxicol Sci. 2016;41(4):511-21. doi: 10.2131/jts.41.511. PubMed PMID: 27432237.

8: Wille T, von der Wellen J, Thiermann H, Worek F. Pseudocatalytic scavenging of the nerve agent VX with human blood components and the oximes obidoxime and HI-6. Arch Toxicol. 2017 Mar;91(3):1309-1318. doi: 10.1007/s00204-016-1776-x. Epub 2016 Jun 29. PubMed PMID: 27358236.

9: Yan L, Chen J, Xu B, Guo L, Xie Y, Tang J, Xie J. A liquid chromatography tandem mass spectrometric method on in vitro nerve agents poisoning characterization and reactivator efficacy evaluation by determination of specific peptide adducts in acetylcholinesterase. J Chromatogr A. 2016 Jun 10;1450:86-93. doi: 10.1016/j.chroma.2016.05.005. Epub 2016 May 3. PubMed PMID: 27179675.

10: Worek F, Koller M, Thiermann H, Wille T. Reactivation of nerve agent-inhibited human acetylcholinesterase by obidoxime, HI-6 and obidoxime+HI-6: Kinetic in vitro study with simulated nerve agent toxicokinetics and oxime pharmacokinetics. Toxicology. 2016 Mar 28;350-352:25-30. doi: 10.1016/j.tox.2016.05.001. Epub 2016 May 3. PubMed PMID: 27153754.

11: Krishnan JKS, Arun P, Appu AP, Vijayakumar N, Figueiredo TH, Braga MFM, Baskota S, Olsen CH, Farkas N, Dagata J, Frey WH 2nd, Moffett JR, Namboodiri AMA. Intranasal delivery of obidoxime to the brain prevents mortality and CNS damage from organophosphate poisoning. Neurotoxicology. 2016 Mar;53:64-73. doi: 10.1016/j.neuro.2015.12.020. Epub 2016 Jan 2. PubMed PMID: 26751814; PubMed Central PMCID: PMC4808345.

12: Myhrer T, Mariussen E, Enger S, Aas P. Supralethal poisoning by any of the classical nerve agents is effectively counteracted by procyclidine regimens in rats. Neurotoxicology. 2015 Sep;50:142-8. doi: 10.1016/j.neuro.2015.08.012. Epub 2015 Aug 28. PubMed PMID: 26318504.

13: Steinritz D, Eyer F, Worek F, Thiermann H, John H. Repetitive obidoxime treatment induced increase of red blood cell acetylcholinesterase activity even in a late phase of a severe methamidophos poisoning: A case report. Toxicol Lett. 2016 Feb 26;244:121-3. doi: 10.1016/j.toxlet.2015.07.010. Epub 2015 Jul 19. PubMed PMID: 26200596.

14: Valiveti AK, Bhalerao UM, Acharya J, Karade HN, Gundapu R, Halve AK, Kaushik MP. Synthesis and in vitro kinetic study of novel mono-pyridinium oximes as reactivators of organophosphorus (OP) inhibited human acetylcholinesterase (hAChE). Chem Biol Interact. 2015 Jul 25;237:125-32. doi: 10.1016/j.cbi.2015.06.007. Epub 2015 Jun 10. PubMed PMID: 26070418.

15: Shrot S, Tauber M, Shiyovich A, Milk N, Rosman Y, Eisenkraft A, Kadar T, Kassirer M, Cohen Y. Early brain magnetic resonance imaging can predict short and long-term outcomes after organophosphate poisoning in a rat model. Neurotoxicology. 2015 May;48:206-16. doi: 10.1016/j.neuro.2015.04.003. Epub 2015 Apr 23. PubMed PMID: 25912464.

16: Kassa J, Sepsova V, Matouskova L, Horova A, Musilek K. A comparison of the reactivating and therapeutic efficacy of two novel bispyridinium oximes (K727, K733) with the oxime HI-6 and obidoxime in sarin-poisoned rats and mice. Toxicol Mech Methods. 2015 Mar;25(3):229-33. doi: 10.3109/15376516.2015.1036333. Epub 2015 Apr 20. PubMed PMID: 25894563.

17: Gazzi EN, Sorodoc V, Petris O, Tarţău L, Dumitrescu G, Sorodoc L, Lupuşoru CE. Butyrylcholinesterase activity-biomarker for predicting the outcome in acute cholinesterase inhibitor poisoning--a 30-year retrospective analysis. Rev Med Chir Soc Med Nat Iasi. 2014 Oct-Dec;118(4):971-8. PubMed PMID: 25581956.

18: Worek F, Elsinghorst P, Koller M, Thiermann H. Reactions of methylphosphonic difluoride with human acetylcholinesterase and oximes--Possible therapeutic implications. Toxicol Lett. 2014 Nov 18;231(1):92-8. doi: 10.1016/j.toxlet.2014.09.012. Epub 2014 Sep 18. PubMed PMID: 25240274.

19: Lo R, Ganguly B. Can hydroxylamine be a more potent nucleophile for the reactivation of tabun-inhibited AChE than prototype oxime drugs? An answer derived from quantum chemical and steered molecular dynamics studies. Mol Biosyst. 2014 Jul 29;10(9):2368-83. doi: 10.1039/c4mb00083h. PubMed PMID: 24964273.

20: Shrot S, Ramaty E, Biala Y, Bar-Klein G, Daninos M, Kamintsky L, Makarovsky I, Statlender L, Rosman Y, Krivoy A, Lavon O, Kassirer M, Friedman A, Yaari Y. Prevention of organophosphate-induced chronic epilepsy by early benzodiazepine treatment. Toxicology. 2014 Sep 2;323:19-25. doi: 10.1016/j.tox.2014.05.010. Epub 2014 Jun 2. PubMed PMID: 24881594.