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MedKoo Cat#: 318595 | Name: Pyridostigmine Bromide
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Description:

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

Pyridostigmine bromide is a cholinesterase inhibitor with a slightly longer duration of action than neostigmine. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.

Chemical Structure

Pyridostigmine Bromide
Pyridostigmine Bromide
CAS#101-26-8

Theoretical Analysis

MedKoo Cat#: 318595

Name: Pyridostigmine Bromide

CAS#: 101-26-8

Chemical Formula: C9H13BrN2O2

Exact Mass:

Molecular Weight: 261.12

Elemental Analysis: C, 41.40; H, 5.02; Br, 30.60; N, 10.73; O, 12.25

Price and Availability

Size Price Availability Quantity
2g USD 350.00 2 Weeks
10g USD 950.00 2 Weeks
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Synonym
Pyridostigmine Bromide; Mestinon; Regonol; Kalimin; Pyridostigmine Br, Pyridostigmine;
IUPAC/Chemical Name
(1-methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate;bromide
InChi Key
VNYBTNPBYXSMOO-UHFFFAOYSA-M
InChi Code
InChI=1S/C9H13N2O2.BrH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1
SMILES Code
C[N+]1=CC=CC(=C1)OC(=O)N(C)C.[Br-]
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 and water
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:
Pyridostigmine bromide binds reversibly to acetylcholinesterase active sites in the peripheral nervous system, thereby preventing the breakdown of acetylcholine. This leads to an accumulation of acetylcholine at cholinergic synapses and facilitates transmission of impulses across the neuromuscular junction.
In vitro activity:
Pyridostigmine bromide effectively inhibited AChE activity in neural SH-SY5Y cells. Pyridostigmine bromide did not induce oxidative stress at lower concentrations but exhibited genotoxic effects at a slightly higher concentration. At the minimal therapeutic dose, pyridostigmine bromide promoted cell proliferation, mitochondrial activity, and telomerase gene upregulation. Pyridostigmine bromide exposure in neural cells did not lead to extensive toxicity or indicative neurodegenerative patterns in this study. Reference: Mutat Res Genet Toxicol Environ Mutagen. 2017 Nov;823:1-10. https://pubmed.ncbi.nlm.nih.gov/28985942/
In vivo activity:
C57BL/6 mice received doses of pyridostigmine bromide physiologically similar to those administered to Gulf War veterans with Gulf War Illness. Pyridostigmine bromide exposure reduced the numbers of enteric neurons, which are responsible for mediating colonic motility reside within the myenteric plexus. Pyridostigmine bromide exposure caused functional and anatomical dysfunction, promoting impaired motility within the colon. Reference: Adv Biol (Weinh). 2023 May;7(5):e2200254. https://pubmed.ncbi.nlm.nih.gov/36802210/
Solvent mg/mL mM
Solubility
DMSO 50.0 191.48
Water 8.8 33.70
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 261.12 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. Azzolin VF, Barbisan F, Lenz LS, Teixeira CF, Fortuna M, Duarte T, Duarte MMFM, da Cruz IBM. Effects of Pyridostigmine bromide on SH-SY5Y cells: An in vitro neuroblastoma neurotoxicity model. Mutat Res Genet Toxicol Environ Mutagen. 2017 Nov;823:1-10. doi: 10.1016/j.mrgentox.2017.08.003. Epub 2017 Aug 31. PMID: 28985942. 2. Lanza A, Stellavato A, Heulfe I, Landi C, Gombos F, Cirillo N. Serum of patients with oral pemphigus vulgaris impairs keratinocyte wound repair in vitro: a time-lapse study on the efficacy of methylprednisolone and pyridostigmine bromide. Oral Dis. 2009 Oct;15(7):478-83. doi: 10.1111/j.1601-0825.2009.01574.x. Epub 2009 Jun 10. PMID: 19519621. 3. Collier CA, Foncerrada S, Clevenger AJ, Shetty A, Raghavan SA. Acute Exposure to Pyridostigmine Bromide Disrupts Cholinergic Myenteric Neuroimmune Function in Mice. Adv Biol (Weinh). 2023 May;7(5):e2200254. doi: 10.1002/adbi.202200254. Epub 2023 Feb 19. PMID: 36802210. 4. Burzynski HE, Macht VA, Woodruff JL, Crawford JN, Erichsen JM, Piroli GG, Grillo CA, Fadel JR, Reagan LP. Pyridostigmine bromide elicits progressive and chronic impairments in the cholinergic anti-inflammatory pathway in the prefrontal cortex and hippocampus of male rats. Neurobiol Stress. 2022 Apr 15;18:100446. doi: 10.1016/j.ynstr.2022.100446. PMID: 35573808; PMCID: PMC9095881.
In vitro protocol:
1. Azzolin VF, Barbisan F, Lenz LS, Teixeira CF, Fortuna M, Duarte T, Duarte MMFM, da Cruz IBM. Effects of Pyridostigmine bromide on SH-SY5Y cells: An in vitro neuroblastoma neurotoxicity model. Mutat Res Genet Toxicol Environ Mutagen. 2017 Nov;823:1-10. doi: 10.1016/j.mrgentox.2017.08.003. Epub 2017 Aug 31. PMID: 28985942. 2. Lanza A, Stellavato A, Heulfe I, Landi C, Gombos F, Cirillo N. Serum of patients with oral pemphigus vulgaris impairs keratinocyte wound repair in vitro: a time-lapse study on the efficacy of methylprednisolone and pyridostigmine bromide. Oral Dis. 2009 Oct;15(7):478-83. doi: 10.1111/j.1601-0825.2009.01574.x. Epub 2009 Jun 10. PMID: 19519621.
In vivo protocol:
1. Collier CA, Foncerrada S, Clevenger AJ, Shetty A, Raghavan SA. Acute Exposure to Pyridostigmine Bromide Disrupts Cholinergic Myenteric Neuroimmune Function in Mice. Adv Biol (Weinh). 2023 May;7(5):e2200254. doi: 10.1002/adbi.202200254. Epub 2023 Feb 19. PMID: 36802210. 2. Burzynski HE, Macht VA, Woodruff JL, Crawford JN, Erichsen JM, Piroli GG, Grillo CA, Fadel JR, Reagan LP. Pyridostigmine bromide elicits progressive and chronic impairments in the cholinergic anti-inflammatory pathway in the prefrontal cortex and hippocampus of male rats. Neurobiol Stress. 2022 Apr 15;18:100446. doi: 10.1016/j.ynstr.2022.100446. PMID: 35573808; PMCID: PMC9095881.
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A novel spectrofluorimetric method for the assay of pseudoephedrine hydrochloride in pharmaceutical formulations via derivatization with 4-chloro-7-nitrobenzofurazan. Luminescence. 2011 Nov-Dec;26(6):510-7. doi: 10.1002/bio.1261. Epub 2010 Nov 8. PubMed PMID: 22162453. 5: Yu LP, Wang XK, Luo JB. [Determination of ephedrine hydrochloride, pseudoephedrine hydrochloride and methylephedrine hydrochloride in maxingshigan decoction by CE]. Zhong Yao Cai. 2011 Apr;34(4):620-3. Chinese. PubMed PMID: 21809550. 6: Zeeshan F, Bukhari NI. Development and evaluation of a novel modified-release pellet-based tablet system for the delivery of loratadine and pseudoephedrine hydrochloride as model drugs. AAPS PharmSciTech. 2010 Jun;11(2):910-6. doi: 10.1208/s12249-010-9456-2. Epub 2010 May 22. PubMed PMID: 20496016; PubMed Central PMCID: PMC2902326. 7: Clinical Research Coordination Group of Guaifenesin Compound Pseudoephedrine Hydrochloride Oral Solution, Lu Q. [A prospective multicenter randomized controlled clinical study on the efficacy and safety of Guaifenesin compound pseudoephedrine hydrochloride oral solution]. Zhonghua Er Ke Za Zhi. 2010 Mar;48(3):204-7. Chinese. PubMed PMID: 20426957. 8: Kikano G. Safety and efficacy of extended-release guaifenesin/pseudoephedrine hydrochloride for adjunctive symptom relief of acute respiratory infections. Postgrad Med. 2009 May;121(3):173-5. doi: 10.3810/pgm.2009.05.2018. PubMed PMID: 19491556. 9: Yang ZY, Lu Y, Tang X. Pseudoephedrine hydrochloride sustained-release pellets prepared by a combination of hot-melt subcoating and polymer coating. Drug Dev Ind Pharm. 2008 Dec;34(12):1323-30. doi: 10.1080/03639040802084938 . PubMed PMID: 18785047. 10: LaForce C, Gentile DA, Skoner DP. A randomized, double-blind, parallel-group, multicenter, placebo-controlled study of the safety and efficacy of extended-release guaifenesin/pseudoephedrine hydrochloride for symptom relief as an adjunctive therapy to antibiotic treatment of acute respiratory infections. Postgrad Med. 2008 Jul;120(2):53-9. doi: 10.3810/pgm.2008.07.1791. PubMed PMID: 18654069. 11: Chitlange SS, Sakarkar DM, Wankhede SB, Wadodkar SG. High performance thin layer chromatographic method for simultaneous estimation of Ibuprofen and pseudoephedrine hydrochloride. Indian J Pharm Sci. 2008 May-Jun;70(3):398-400. doi: 10.4103/0250-474X.43018. PubMed PMID: 20046759; PubMed Central PMCID: PMC2792507. 12: Zayed SI, Issa YM, Hussein A. Construction and performance characterization of ion-selective electrodes for potentiometric determination of pseudoephedrine hydrochloride applying batch and flow injection analysis techniques. Ann Chim. 2006 Jul-Aug;96(7-8):421-33. PubMed PMID: 16948431. 13: Likar MD, Mansour HL, Harwood JW. Development and validation of a dissolution test for a once-a-day combination tablet of immediate-release cetirizine dihydrochloride and extended-release pseudoephedrine hydrochloride. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):543-51. PubMed PMID: 15975755. 14: Gu X, Li H, Macnair KR, Simons FE, Simons KJ. Simultaneous analysis of the H1-antihistamine acrivastine and the decongestant pseudoephedrine hydrochloride by high-performance liquid chromatography. J Pharm Biomed Anal. 2005 Apr 1;37(4):663-7. Epub 2004 Dec 25. PubMed PMID: 15797786. 15: Safak MA, Kiliç R, Haberal I, Göçmen H, Ozeri C. A comparative study of azithromycin and pseudoephedrine hydrochloride for otitis media with effusion in children. Acta Otolaryngol. 2001 Dec;121(8):925-9. PubMed PMID: 11813896. 16: Ekpe A, Tong JH, Rodriguez L. High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities. J Chromatogr Sci. 2001 Mar;39(3):81-6. PubMed PMID: 11277256. 17: Altuntas TG, Zanooz SS, Nebioglu D. Quantitative determination of acrivastine and pseudoephedrine hydrochloride in pharmaceutical formulation by high performance liquid chromatography and derivative spectrophotometry. J Pharm Biomed Anal. 1998 May;17(1):103-9. PubMed PMID: 9608432. 18: Hindioğlu U, Sahin S. Nonpigmenting solitary fixed drug eruption caused by pseudoephedrine hydrochloride. J Am Acad Dermatol. 1998 Mar;38(3):499-500. PubMed PMID: 9520039. 19: Dash AK. Determination of pseudoephedrine hydrochloride in dosage forms by liquid chromatography. J Pharm Biomed Anal. 1994 Dec;12(12):1601-6. PubMed PMID: 7696386. 20: Akhtar MJ, Khan S, Hafiz M. 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