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MedKoo Cat#: 318556 | Name: Pralidoxime Chloride
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Description:

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

Pralidoxime Chloride binds to inactivated acetylcholinesterases and is used to combat organophosphates and nerve agent poisoning. 2-PAM is currently the only FDA approved oxime in the United States.

Chemical Structure

Pralidoxime Chloride
Pralidoxime Chloride
CAS# 51-15-0 (Cl)

Theoretical Analysis

MedKoo Cat#: 318556

Name: Pralidoxime Chloride

CAS#: 51-15-0 (Cl)

Chemical Formula: C7H9ClN2O

Exact Mass:

Molecular Weight: 172.61

Elemental Analysis: C, 48.71; H, 5.26; Cl, 20.54; N, 16.23; O, 9.27

Price and Availability

Size Price Availability Quantity
2g USD 350.00 2 Weeks
5g USD 550.00 2 Weeks
10g USD 950.00 2 Weeks
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Related CAS #
154-97-2 (mesylate); 94-63-3 (iodide); 51-15-0 (Cl)
Synonym
Pralidoxime Chloride; 2-PAM chloride; Pralidoxime; Pralidoxine chloride; ComboPen; Protopam chloride; pralidoxime, 14C-labeled; pralidoxime methyl sulfate; pralidoxime nitrate (1:1);
IUPAC/Chemical Name
[(E)-(1-methylpyridin-2-ylidene)methyl]-oxoazanium;chloride
InChi Key
HIGSLXSBYYMVKI-NAFXZHHSSA-N
InChi Code
InChI=1S/C7H8N2O.ClH/c1-9-5-3-2-4-7(9)6-8-10;/h2-6H,1H3;1H/b7-6-;
SMILES Code
CN1C=CC=CC1=C[NH+]=O.[Cl-]
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, not in water
Shelf Life
>2 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pralidoxime chloride 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 comments
Solubility
DMSO 11.3 65.67
Ethanol 1.0 5.79
PBS (pH 7.2) 10.0 57.93
Water 67.0 388.15
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 172.61 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
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. 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.
1: Liu HX, Liu CF, Yang WH. Clinical study of continuous micropump infusion of atropine and pralidoxime chloride for treatment of severe acute organophosphorus insecticide poisoning. J Chin Med Assoc. 2015 Dec;78(12):709-13. doi: 10.1016/j.jcma.2015.08.006. Epub 2015 Oct 3. PubMed PMID: 26441220. 2: Banerjee S, Chattopadhyay P, Ghosh A, Bhatnagar A, Veer V. Pharmacokinetic and biodistribution study of eserine and pralidoxime chloride in rabbits following a single application of a transdermal patch. Eur J Drug Metab Pharmacokinet. 2014 Dec 30. [Epub ahead of print] PubMed PMID: 25547639. 3: Banerjee S, Chattopadhyay P, Ghosh A, Pathak MP, Gogoi J, Veer V. Protection by a transdermal patch containing eserine and pralidoxime chloride for prophylaxis against (±)-Anatoxin A poisoning in rats. Eur J Pharm Sci. 2014 Jun 2;56:28-36. doi: 10.1016/j.ejps.2014.01.013. Epub 2014 Feb 14. PubMed PMID: 24530375. 4: Lucyk S, Vilensky D, Fok PT, Nelson LS. Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides. Toxicol Sci. 2014 Apr;138(2):482. doi: 10.1093/toxsci/kft337. Epub 2014 Jan 2. PubMed PMID: 24385419. 5: Connors NJ, Weber BJ, Hoffman RS. Regarding "Repeated pulse intramuscular injection of pralidoxime chloride in severe acute organophosphorus pesticide poisoning". Am J Emerg Med. 2013 Dec;31(12):1711-2. doi: 10.1016/j.ajem.2013.08.052. Epub 2013 Oct 1. PubMed PMID: 24091197. 6: Konickx LA, Worek F, Jayamanne S, Thiermann H, Buckley NA, Eddleston M. Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides. Toxicol Sci. 2013 Dec;136(2):274-83. doi: 10.1093/toxsci/kft217. Epub 2013 Sep 19. PubMed PMID: 24052565; PubMed Central PMCID: PMC3858199. 7: Banerjee S, Chattopadhyay P, Ghosh A, Kaity S, Veer V. Development and validation of a reverse phase liquid chromatography method for the simultaneous quantification of eserine and pralidoxime chloride in drugs-in-adhesive matrix type transdermal patches. Drug Res (Stuttg). 2013 Sep;63(9):450-6. doi: 10.1055/s-0033-1343471. Epub 2013 Apr 30. PubMed PMID: 23633237. 8: Tang X, Wang R, Xie H, Hu J, Zhao W. Repeated pulse intramuscular injection of pralidoxime chloride in severe acute organophosphorus pesticide poisoning. Am J Emerg Med. 2013 Jun;31(6):946-9. doi: 10.1016/j.ajem.2013.03.012. Epub 2013 May 14. PubMed PMID: 23680326. 9: Khan FA, Campbell AJ, Hoyt B, Herdman C, Ku T, Thangavelu S, Gordon RK. Oxidative mechanisms for the biotransformation of 1-methyl-1,6-dihydropyridine-2-carbaldoxime to pralidoxime chloride. Life Sci. 2011 Dec 19;89(25-26):911-7. doi: 10.1016/j.lfs.2011.09.019. Epub 2011 Oct 4. PubMed PMID: 21989207. 10: Fu Z, Huang X, Xiao H, Huang J. [Determination of pralidoxime chloride in rat plasma by high performance liquid chromatography]. Wei Sheng Yan Jiu. 2005 Mar;34(2):255-6. Chinese. PubMed PMID: 15952678. 11: Tian YP, Gao HB, Tong F, Qiu ZW, Su JL. [One case of using pralidoxime chloride to treat acute parathion poisoning]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2004 Feb;22(1):38. Chinese. PubMed PMID: 15033016. 12: Yamane GK. Accidental injection of a U.S. Air Force aviator by a pralidoxime chloride auto-injector: a case report. Aviat Space Environ Med. 1999 Nov;70(11):1110-2. PubMed PMID: 10608609. 13: Ekins BR, Geller RJ. Methomyl-induced carbamate poisoning treated with pralidoxime chloride. West J Med. 1994 Jul;161(1):68-70. PubMed PMID: 7941519; PubMed Central PMCID: PMC1011381. 14: Karljiković-Rajić K, Stanković B. Potentiometric investigation of the stability of palladium(II) complex of pralidoxime chloride in aqueous solution. J Pharm Biomed Anal. 1990;8(8-12):705-9. PubMed PMID: 2100611. 15: Friedl KE, Hannan CJ Jr, Schadler PW, Jacob WH. Atropine absorption after intramuscular administration with 2-pralidoxime chloride by two automatic injector devices. J Pharm Sci. 1989 Sep;78(9):728-31. PubMed PMID: 2585264. 16: Jeevarathinam K, Ghosh AK, Srinivasan A, Das Gupta S. Pharmacokinetics of pralidoxime chloride and its correlation to therapeutic efficacy against diisopropyl fluorophosphate intoxication in rats. Pharmazie. 1988 Feb;43(2):114-5. PubMed PMID: 3393576. 17: Thompson DF. Pralidoxime chloride continuous infusions. Ann Emerg Med. 1987 Jul;16(7):831-2. PubMed PMID: 3592350. 18: Fyhr P, Brodin A, Ernerot L, Lindquist J. Degradation pathway of pralidoxime chloride in concentrated acidic solution. J Pharm Sci. 1986 Jun;75(6):608-11. PubMed PMID: 3735107. 19: Bhuta SI, Sugita ET, Niebergall PJ, Schnaare RL. Influence of various anions on intestinal disappearance of hexamethonium chloride and pralidoxime chloride in rats. J Pharm Sci. 1980 Aug;69(8):923-8. PubMed PMID: 7400937. 20: Lemanowicz EF, Sugita ET, Niebergall PJ, Schnaare RL. Kinetics of absorption and elimination of pralidoxime chloride in dogs. J Pharm Sci. 1979 Feb;68(2):141-5. PubMed PMID: 423079.