Synonym
Neostigmine bromide
IUPAC/Chemical Name
3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium bromide
InChi Key
LULNWZDBKTWDGK-UHFFFAOYSA-M
InChi Code
InChI=1S/C12H19N2O2.BrH/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;/h6-9H,1-5H3;1H/q+1;/p-1
SMILES Code
C[N+](C)(C)C1=CC=CC(OC(N(C)C)=O)=C1.[Br-]
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
Biological target:
Neostigmine Bromide is a cholinesterase inhibitor used in the treatment of myasthenia gravis.
In vitro activity:
In this study, the cytotoxicity, genotoxicity and apoptotic effects of Sugammadex and Neostigmine on HEK-293 cells were analyzed with using the MTT, Comet Assay and Flow Cytometric Annexin-V methods, respectively. The results demonstrate that Neostigmine at 50, 100, 250, and 500 µg/mL is more cytotoxic than equivalent dosages of Sugammadex. Neostigmine at 500 and 1000 µg/mL was found to be more genotoxic, and Neostigmine at 500 µg/mL had a statistically higher risk of causing apoptosis and necrosis than Sugammadex (p<0.05).
Reference: Cell Mol Biol (Noisy-le-grand). 2018 Oct 30;64(13):74-78. https://pubmed.ncbi.nlm.nih.gov/30403599/
In vivo activity:
In this sense, the aim of this study is to investigate the effects of treatment with neostigmine, known for the ability to control lung inflammation, on oxidative stress in the cerebral cortex of asthmatic mice. Female BALB/cJ mice were submitted to asthma model induced by ovalbumin (OVA). Control group received only Dulbecco's phosphate-buffered saline (DPBS). To evaluate neostigmine effects, mice received 80 μg/kg of neostigmine intraperitoneally 30 min after each OVA challenge. The results revealed for the first time that treatment with neostigmine (an acetylcholinesterase inhibitor that no crosses the BBB) was able to revert ROS production and change anti-oxidant enzyme catalase in the cerebral cortex in asthmatic mice.
Reference: Metab Brain Dis. 2020 Jun;35(5):765-774. https://pubmed.ncbi.nlm.nih.gov/32189127/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
329.82 |
| Water |
80.0 |
263.85 |
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
303.20
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. Büyükfırat E, Koyuncu İ, Karahan MA, Binici O, Altay N, Kirmit A, Gönel A. Comparison of the cytotoxic, genotoxic and apoptotic effects of Sugammadex and Neostigmine on human embryonic renal cell (HEK-293). Cell Mol Biol (Noisy-le-grand). 2018 Oct 30;64(13):74-78. PMID: 30403599.
2. Mustafa S, Ismael HN. Reactivity of diabetic urinary bladder to the cholinesterase inhibitor neostigmine. Urology. 2014 Dec;84(6):1549.e1-5. doi: 10.1016/j.urology.2014.08.019. Epub 2014 Oct 14. PMID: 25440827.
3. Antunes GL, Silveira JS, Kaiber DB, Luft C, Dos Santos TM, Marques EP, Ferreira FS, Schmitz F, de Souza Wyse AT, Stein RT, Pitrez PM, da Cunha AA. Neostigmine treatment induces neuroprotection against oxidative stress in cerebral cortex of asthmatic mice. Metab Brain Dis. 2020 Jun;35(5):765-774. doi: 10.1007/s11011-020-00558-7. Epub 2020 Mar 18. PMID: 32189127.
4. Fogaça MV, Fedoce AG, Ferreira-Junior NC, Guimarães FS, Resstel LB. Involvement of M1 and CB₁ receptors in the anxiogenic-like effects induced by neostigmine injected into the rat prelimbic medial prefrontal cortex. Psychopharmacology (Berl). 2016 Apr;233(8):1377-85. doi: 10.1007/s00213-016-4228-7. Epub 2016 Feb 13. PMID: 26873081.
In vitro protocol:
1. Büyükfırat E, Koyuncu İ, Karahan MA, Binici O, Altay N, Kirmit A, Gönel A. Comparison of the cytotoxic, genotoxic and apoptotic effects of Sugammadex and Neostigmine on human embryonic renal cell (HEK-293). Cell Mol Biol (Noisy-le-grand). 2018 Oct 30;64(13):74-78. PMID: 30403599.
2. Mustafa S, Ismael HN. Reactivity of diabetic urinary bladder to the cholinesterase inhibitor neostigmine. Urology. 2014 Dec;84(6):1549.e1-5. doi: 10.1016/j.urology.2014.08.019. Epub 2014 Oct 14. PMID: 25440827.
In vivo protocol:
1. Antunes GL, Silveira JS, Kaiber DB, Luft C, Dos Santos TM, Marques EP, Ferreira FS, Schmitz F, de Souza Wyse AT, Stein RT, Pitrez PM, da Cunha AA. Neostigmine treatment induces neuroprotection against oxidative stress in cerebral cortex of asthmatic mice. Metab Brain Dis. 2020 Jun;35(5):765-774. doi: 10.1007/s11011-020-00558-7. Epub 2020 Mar 18. PMID: 32189127.
2. Fogaça MV, Fedoce AG, Ferreira-Junior NC, Guimarães FS, Resstel LB. Involvement of M1 and CB₁ receptors in the anxiogenic-like effects induced by neostigmine injected into the rat prelimbic medial prefrontal cortex. Psychopharmacology (Berl). 2016 Apr;233(8):1377-85. doi: 10.1007/s00213-016-4228-7. Epub 2016 Feb 13. PMID: 26873081.
1: Storms ML Bs, Stewart JT Phd, Warren FW Ms Rph. Stability of neostigmine methylsulfate injection at ambient temperature and 4 deg C in polypropylene syringes. Int J Pharm Compd. 2002 Nov-Dec;6(6):475-7. PubMed PMID: 23979474.
2: Shafer SL, Eisenach JC, Hood DD, Tong C. Cerebrospinal fluid pharmacokinetics and pharmacodynamics of intrathecal neostigmine methylsulfate in humans. Anesthesiology. 1998 Nov;89(5):1074-88. PubMed PMID: 9821995.
3: Hood DD, Eisenach JC, Tong C, Tommasi E, Yaksh TL. Cardiorespiratory and spinal cord blood flow effects of intrathecal neostigmine methylsulfate, clonidine, and their combination in sheep. Anesthesiology. 1995 Feb;82(2):428-35. PubMed PMID: 7856901.
4: Yaksh TL, Grafe MR, Malkmus S, Rathbun ML, Eisenach JC. Studies on the safety of chronically administered intrathecal neostigmine methylsulfate in rats and dogs. Anesthesiology. 1995 Feb;82(2):412-27. PubMed PMID: 7856900.
5: Hood DD, Eisenach JC, Tuttle R. Phase I safety assessment of intrathecal neostigmine methylsulfate in humans. Anesthesiology. 1995 Feb;82(2):331-43. PubMed PMID: 7856891.
6: Adams SB, MacHarg MA. Neostigmine methylsulfate delays gastric emptying of particulate markers in horses. Am J Vet Res. 1985 Dec;46(12):2498-9. PubMed PMID: 4083582.
7: Kucherenko ME, Havrylej VI. [Effect of x-irradiation, nicotinic acid and neostigmine methylsulfate on the interrelation between methylation and biosynthesis of tRNA]. Ukr Biokhim Zh. 1977 Sep-Oct;49(5):3-8. Ukrainian. PubMed PMID: 919054.
8: Kawabuchi M, Osame M, Watanabe S, Igata A, Kanaseki T. Myopathic changes at the end-plate region induced by neostigmine methylsulfate. Experientia. 1976 May 15;32(5):632-5. PubMed PMID: 179842.
9: Ward MD, Forbes MS, Johns TR. Neostigmine methylsulfate. Does it have a chronic effect as well as a transient one? Arch Neurol. 1975 Dec;32(12):808-13. PubMed PMID: 173268.
10: Kawabuchi M, Osame M, Watanabe S, Igata A, Kanaseki T. [Changes in the neuromuscular junction and striated muscle fiber following the administration of neostigmine methylsulfate in rats. A morphological observation (author's transl)]. Fukuoka Igaku Zasshi. 1975 Aug 25;66(8):500-11. Japanese. PubMed PMID: 1237456.
11: Kling RE. Structure of alkaline hydrolysis products of neostigmine methylsulfate and neostigmine bromide. J Assoc Off Anal Chem. 1974 May;57(3):721-4. PubMed PMID: 4833414.
12: Kling RE. UV spectrophotometric assay of neostigmine methylsulfate as the alkaline hydrolysis product, 3-dimethylaminophenol. J Assoc Off Anal Chem. 1971 Jan;54(1):21-6. PubMed PMID: 5162508.
13: Bridenbaugh PO, Churchll-Davidson HC. Response to tubocurarine chloride and its reversal by neostigmine methylsulfate in man. JAMA. 1968 Feb 19;203(8):541-4. PubMed PMID: 5694188.
14: LONG JP, ECKSTEIN JW. Ganglionic actions of neostigmine methylsulfate. J Pharmacol Exp Ther. 1961 Aug;133:216-22. PubMed PMID: 13763330.
15: GARVERICK WW, BURCH GR. Treatment of equine colic with neostigmine methylsulfate. J Am Vet Med Assoc. 1954 Jun;124(927):472-3. PubMed PMID: 13162911.
16: TEITELBAUM HA, VYNER HL. Neostigmine methylsulfate therapy in hemiplegia. Arch Neurol Psychiatry. 1949 Jul;62(1):93-8. PubMed PMID: 18147411.
17: HINMAN CH, ROBY CC. Tolerance trial of neostigmine methylsulfate in pregnancy. Am J Obstet Gynecol. 1949 Mar;57(3):586-8. PubMed PMID: 18123869.
18: BLATTNER RJ, GOODFRIEND J, WEBB BD. The use of neostigmine methylsulfate in infectious neuronitis; report of a case with involvement of respiratory muscles. J Am Med Assoc. 1947 Aug 9;134(15):1235-7. PubMed PMID: 20253936.
19: BELL JE Jr, BOONE JA. Neostigmine methylsulfate an apparent specific for arachnidism (black widow spider bite). J Am Med Assoc. 1945 Dec 8;129:1016. PubMed PMID: 21003747.
