Pralidoxime iodide | CAS# 94-63-3 (iodide) | Cholinesterase Reactivator

MedKoo Cat#: 592128 | Name: Pralidoxime iodide

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Description:

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

Pralidoxime iodide is a Cholinesterase Reactivator.

Chemical Structure

Pralidoxime iodide

CAS#94-63-3 (iodide)

Theoretical Analysis

MedKoo Cat#: 592128

Name: Pralidoxime iodide

CAS#: 94-63-3 (iodide)

Chemical Formula: C7H9IN2O

Exact Mass: 263.9760

Molecular Weight: 264.07

Elemental Analysis: C, 31.84; H, 3.44; I, 48.06; N, 10.61; O, 6.06

Price and Availability

Size	Price	Availability	Quantity
25g	USD 280.00
100g	USD 540.00

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Related CAS #

154-97-2 (mesylate); 94-63-3 (iodide); 51-15-0 (Cl)

Synonym

Pralidoxime iodide; NSC-7760; NSC 7760; NSC7760

IUPAC/Chemical Name

2-Pyridine aldoxime iodomethylate

InChi Key

KGQDCJOBGLAUBQ-HAAWTFQLSA-N

InChi Code

InChI=1S/C6H6N2O.CH3I/c9-8-5-6-3-1-2-4-7-6;1-2/h1-5,9H;1H3/b8-5+;

SMILES Code

O/N=C/C1=NC=CC=C1.CI

Appearance

Solid powder

Purity

>98% (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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pralidoxime iodide is a potent reactivator of acetylcholinesterase (AChE).

In vitro activity:

TBD

In vivo activity:

In the survival study, 6 (27.2%), 15 (68.1%), and 5 (22.7%) animals survived the entire 24-hour monitoring period in the saline, pralidoxime, and norepinephrine groups, respectively (log-rank test P = 0.006). In the hemodynamic study, pralidoxime but not norepinephrine increased end-diastolic volume (P <0.001), stroke volume (P = 0.002), cardiac output (P = 0.003), mean arterial pressure (P = 0.041), and stroke work (P <0.001). The pressor effect of norepinephrine was short-lived, such that by 60 minutes after the initiation of norepinephrine infusion, it no longer had any significant effect on mean arterial pressure. In addition, norepinephrine significantly increased heart rate (P <0.001) and the ratio of arterial elastance to ventricular end-systolic elastance (P = 0.010), but pralidoxime did not. In conclusion, pralidoxime improved the hemodynamics and 24-hour survival rate in rats with peritonitis-induced sepsis, but norepinephrine did not. Reference: PLoS One. 2021 Apr 6;16(4):e0249794. https://pubmed.ncbi.nlm.nih.gov/33822820/

	Solvent	mg/mL	mM
Solubility
	DMSO	151.0	571.83

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 264.07 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.

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

Formulation protocol:

1. Mamadjonov N, Jung YH, Jeung KW, Lee HY, Lee BK, Youn CS, Jeong IS, Heo T, Min YI. Pralidoxime improves the hemodynamics and survival of rats with peritonitis-induced sepsis. PLoS One. 2021 Apr 6;16(4):e0249794. doi: 10.1371/journal.pone.0249794. PMID: 33822820; PMCID: PMC8023460. 2. Lee HY, Mamadjonov N, Jeung KW, Jung YH, Lee BK, Moon KS, Heo T, Min YI. Pralidoxime-Induced Potentiation of the Pressor Effect of Adrenaline and Hastened Successful Resuscitation by Pralidoxime in a Porcine Cardiac Arrest Model. Cardiovasc Drugs Ther. 2020 Oct;34(5):619-628. doi: 10.1007/s10557-020-07026-5. Epub 2020 Jun 19. PMID: 32562104.

In vitro protocol:

TBD

In vivo protocol:

1: Zhang Y, Bromberg L, Lin Z, Brown P, Van Voorhis T, Hatton TA. Polydiacetylene functionalized with charged termini for device-free colorimetric detection of malathion. J Colloid Interface Sci. 2018 Apr 27;528:27-35. doi: 10.1016/j.jcis.2018.04.098. [Epub ahead of print] PubMed PMID: 29807353. 2: Hou R, Zhang H, Chen H, Zhou Y, Long Y, Liu D. Total pancreatic necrosis after organophosphate intoxication. Front Med. 2018 May 18. doi: 10.1007/s11684-018-0626-z. [Epub ahead of print] PubMed PMID: 29777518. 3: Houzé P, Berthin T, Raphalen JH, Hutin A, Baud JF. High Dose of Pralidoxime Reverses Paraoxon-Induced Respiratory Toxicity in Mice. Turk J Anaesthesiol Reanim. 2018 Apr;46(2):131-138. doi: 10.5152/TJAR.2018.29660. Epub 2018 Apr 1. PubMed PMID: 29744248; PubMed Central PMCID: PMC5937459. 4: 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. 5: Stolbach A, Bebarta V, Beuhler M, Carstairs S, Nelson L, Wahl M, Wax PM, McKay C. ACMT Position Statement: Alternative or Contingency Countermeasures for Acetylcholinesterase Inhibiting Agents. J Med Toxicol. 2018 Apr 17. doi: 10.1007/s13181-018-0658-4. [Epub ahead of print] PubMed PMID: 29667118. 6: Wiercinski A, Jackson JP. Nerve Agents. 2018 Mar 7. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK493158/ PubMed PMID: 29630210. 7: Kolesnikov AM, Yuidin MA, Nikiforov AS, Ivanov IM, Vengerovich NG, Makacheev AS. Study of the Oxime-induced Reactivation of Acetyl- and Butyrylcholinesterase of Human with Inhibition of Organophosphorus Insecticide In Vitro. Bull Exp Biol Med. 2018 Mar;164(5):624-628. doi: 10.1007/s10517-018-4046-5. Epub 2018 Mar 26. PubMed PMID: 29577198. 8: Kuca K, Musilek K, Jun D, Zdarova-Karasova J, Nepovimova E, Soukup O, Hrabinova M, Mikler J, Franca TCC, Da Cunha EFF, De Castro AA, Valis M, Ramalho TC. A newly developed oxime K203 is the most effective reactivator of tabun-inhibited acetylcholinesterase. BMC Pharmacol Toxicol. 2018 Feb 21;19(1):8. doi: 10.1186/s40360-018-0196-3. PubMed PMID: 29467029; PubMed Central PMCID: PMC5822599. 9: Muckova L, Pejchal J, Jost P, Vanova N, Herman D, Jun D. Cytotoxicity of acetylcholinesterase reactivators evaluated in vitro and its relation to their structure. Drug Chem Toxicol. 2018 Feb 9:1-5. doi: 10.1080/01480545.2018.1432641. [Epub ahead of print] PubMed PMID: 29421945. 10: Kizilyildiz BS, Karaman K, Özen S, Üner A. Acute intoxications among Turkish children. Minerva Pediatr. 2018 Feb;70(1):46-50. doi: 10.23736/S0026-4946.16.04254-7. PubMed PMID: 29363292. 11: Blumenberg A, Benabbas R, deSouza IS, Conigliaro A, Paladino L, Warman E, Sinert R, Wiener SW. Utility of 2-Pyridine Aldoxime Methyl Chloride (2-PAM) for Acute Organophosphate Poisoning: A Systematic Review and Meta-Analysis. J Med Toxicol. 2018 Mar;14(1):91-98. doi: 10.1007/s13181-017-0636-2. Epub 2017 Dec 11. Review. Erratum in: J Med Toxicol. 2018 Jan 3;:. PubMed PMID: 29230717; PubMed Central PMCID: PMC6013731. 12: Candiotti K. Correction to: A primer on nerve agents: what the emergency responder, anesthesiologist, and intensivist needs to know. Can J Anaesth. 2018 Jan;65(1):141-142. doi: 10.1007/s12630-017-1005-y. PubMed PMID: 29164527. 13: Rosenberg YJ, Wang J, Ooms T, Rajendran N, Mao L, Jiang X, Lees J, Urban L, Momper JD, Sepulveda Y, Shyong YJ, Taylor P. Post-exposure treatment with the oxime RS194B rapidly reactivates and reverses advanced symptoms of lethal inhaled paraoxon in macaques. Toxicol Lett. 2018 Sep 1;293:229-234. doi: 10.1016/j.toxlet.2017.10.025. Epub 2017 Nov 9. PubMed PMID: 29129799; PubMed Central PMCID: PMC5943181. 14: Whitmore C, Cook AR, Mann T, Price ME, Emery E, Roughley N, Flint D, Stubbs S, Armstrong SJ, Rice H, Tattersall JEH. The efficacy of HI-6 DMS in a sustained infusion against percutaneous VX poisoning in the guinea-pig. Toxicol Lett. 2018 Sep 1;293:207-215. doi: 10.1016/j.toxlet.2017.11.007. Epub 2017 Nov 10. PubMed PMID: 29129798. 15: 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. PubMed PMID: 29098328. 16: Xie LN, Huang CH, Xu D, Li F, Zhu JG, Shen C, Shao B, Gao HY, Kalyanaraman B, Zhu BZ. Unusual Double Beckmann Fragmentation Reaction under Physiological Conditions. J Org Chem. 2017 Dec 15;82(24):13084-13092. doi: 10.1021/acs.joc.7b02106. Epub 2017 Nov 27. PubMed PMID: 29096055. 17: de Koning MC, Joosen MJA, Worek F, Nachon F, van Grol M, Klaassen SD, Alkema DPW, Wille T, de Bruijn HM. Application of the Ugi Multicomponent Reaction in the Synthesis of Reactivators of Nerve Agent Inhibited Acetylcholinesterase. J Med Chem. 2017 Nov 22;60(22):9376-9392. doi: 10.1021/acs.jmedchem.7b01083. Epub 2017 Nov 13. PubMed PMID: 29091431. 18: Yu ZK, Gong ZJ, Jian XD, Qu AJ. [Clinical effect of alanyl glutamine in the treatment of patients with gastrointestinal function obstacle caused by severe phorate poisoning]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2017 Jul 20;35(7):501-504. doi: 10.3760/cma.j.issn.1001-9391.2017.07.006. Chinese. PubMed PMID: 29081098. 19: Mohammadi H, Jalilian J, Karimi MY, Shetab-Boushehri SV. In Vitro Cysteine Reactivates Organophosphate Insecticide Dichlorvos-Inhibited Human Cholinesterases. Sultan Qaboos Univ Med J. 2017 Aug;17(3):e293-e300. doi: 10.18295/squmj.2017.17.03.006. Epub 2017 Oct 10. Erratum in: Sultan Qaboos Univ Med J. 2017 Nov;17 (4):e493. PubMed PMID: 29062551; PubMed Central PMCID: PMC5642358. 20: Niessen KV, Seeger T, Rappenglück S, Wein T, Höfner G, Wanner KT, Thiermann H, Worek F. In vitro pharmacological characterization of the bispyridinium non-oxime compound MB327 and its 2- and 3-regioisomers. Toxicol Lett. 2018 Sep 1;293:190-197. doi: 10.1016/j.toxlet.2017.10.009. Epub 2017 Oct 10. PubMed PMID: 29024789.