Esomeprazole magnesium | CAS# 161973-10-0 | Biochemical

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

MedKoo CAT#: 576133

CAS#: 161973-10-0 (magnesium)

Description: Esomeprazole magnesium is the magnesium salt of esomeprazole, the S-isomer of omeprazole, with gastric proton pump inhibitor activity. In the acidic compartment of parietal cells, esomeprazole is protonated and converted into the active achiral sulphenamide; the active sulphenamide forms one or more covalent disulfide bonds with the proton pump hydrogen-potassium adenosine triphosphatase (H+/K+ ATPase), thereby inhibiting its activity and the parietal cell secretion of H+ ions into the gastric lumen, the final step in gastric acid production. H+/K+ ATPase is an integral membrane protein of the gastric parietal cell.

Chemical Structure

Esomeprazole magnesium

CAS# 161973-10-0 (magnesium)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 576133
Name: Esomeprazole magnesium
CAS#: 161973-10-0 (magnesium)
Chemical Formula: C34H36MgN6O6S2
Exact Mass: 0.00
Molecular Weight: 713.120
Elemental Analysis: C, 57.27; H, 5.09; Mg, 3.41; N, 11.79; O, 13.46; S, 8.99

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 285	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 161796-78-7(sodium) 119141-88-7(free) 161973-10-0 (magnesium) 217087-09-7 (magnesium hydrate) 161796-84-5 (potassium) 914613-86-8 (strontium anhydrous)

Synonym: H 199/18; Esomeprazole magnesium; Perprazole; (–)-Omeprazole Magnesium; (S)-Omeprazole Magnesium

IUPAC/Chemical Name: magnesium (S)-5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide

InChi Key: KWORUUGOSLYAGD-UHFFFAOYSA-N

InChi Code: InChI=1S/2C17H18N3O3S.Mg/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;/h2*5-8H,9H2,1-4H3;/q2*-1;+2

SMILES Code: CC(C=NC(CS1=O[Mg+2]2([N]3=C(S(CC4=C(C(OC)=C(C=N4)C)C)=O2)[N-]C5=C3C=CC(OC)=C5)[N]6=C1[N-]C7=C6C=CC(OC)=C7)=C8C)=C8OC

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: >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:

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Biological target:	Esomeprazole magnesium ((S)-Omeprazole magnesium) is a potent and orally active H+, K+-ATPase inhibitor.
In vitro activity:	This study found that the expression of both DDAH and iNOS were significantly downregulated by esomeprazole (Fig. 1). For example, the gene expression of iNOS was increased by about 100-fold upon induction with bleomycin, and treatment with esomeprazole decreased the induction in iNOS expression by about 25-fold (Fig. 1). Reference: J Inflamm (Lond). 2021; 18: 17. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8136131/
In vivo activity:	The administration of esomeprazole in different doses significantly reduced the MDA levels in the HE+WIR group (P=0.0001<0.001) and the LE+WIR group (P=0.0001<0.001) (Figure 4A; Table 3). Compared with the NS group, the level of GSH in the WIR group was declined (P=0.012<0.05), which was rescued by the high-dose esomeprazole treatment (P=0.036<0.05) (Figure 4B; Table 3). The assessment revealed that the WIR treatment significantly reduced the levels of SOD relative to that of the NS group (P=0.025<0.05), and this condition was reversed by the prophylactic administration of the high-dose esomeprazole (P=0.048<0.05) (Figure 4C; Table 3). The rats in the HE group did not show any significant changes in the levels of MDA (P=0.963), GSH (P=0.980), SOD (P=0.875) and SOD1 (P=0.809) in the stomach tissue compared with the NS group rats (Figure 4A–D). Reference: Drug Des Devel Ther. 2019; 13: 2969–2984. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6709796/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	96.0	134.62
	DMF	25.0	35.06
	DMF:PBS (pH 7.2) (1:1)	0.5	0.70
	Ethanol	72.0	100.96

Preparing Stock Solutions

The following data is based on the product molecular weight 713.12 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.

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. Ebrahimpour A, Wang M, Li L, Jegga AG, Bonnen MD, Eissa NT, Raghu G, Jyothula S, Kheradmand F, Hanania NA, Rosas IO, Ghebre YT. Esomeprazole attenuates inflammatory and fibrotic response in lung cells through the MAPK/Nrf2/HO1 pathway. J Inflamm (Lond). 2021 May 19;18(1):17. doi: 10.1186/s12950-021-00284-6. PMID: 34011367; PMCID: PMC8136131. 2. Xu Q, Jia X, Wu Q, Shi L, Ma Z, Ba N, Zhao H, Xia X, Zhang Z. Esomeprazole affects the proliferation, metastasis, apoptosis and chemosensitivity of gastric cancer cells by regulating lncRNA/circRNA-miRNA-mRNA ceRNA networks. Oncol Lett. 2020 Dec;20(6):329. doi: 10.3892/ol.2020.12193. Epub 2020 Oct 6. PMID: 33101498; PMCID: PMC7577076. 3. Xie W, Huang X, Chen R, Chen R, Li T, Wu W, Huang Z. Esomeprazole alleviates the damage to stress ulcer in rats through not only its antisecretory effect but its antioxidant effect by inactivating the p38 MAPK and NF-κB signaling pathways. Drug Des Devel Ther. 2019 Aug 22;13:2969-2984. doi: 10.2147/DDDT.S193641. PMID: 31686780; PMCID: PMC6709796. 4. Pham N, Ludwig MS, Wang M, Ebrahimpour A, Bonnen MD, Diwan AH, Kim SJ, Bryan J, Newton JM, Sikora AG, Donovan DT, Sandulache V, Ghebre YT. Topical Esomeprazole Mitigates Radiation-Induced Dermal Inflammation and Fibrosis. Radiat Res. 2019 Nov;192(5):473-482. doi: 10.1667/RR15398.1. Epub 2019 Aug 15. PMID: 31415221; PMCID: PMC6876297.
In vitro protocol:	1. Ebrahimpour A, Wang M, Li L, Jegga AG, Bonnen MD, Eissa NT, Raghu G, Jyothula S, Kheradmand F, Hanania NA, Rosas IO, Ghebre YT. Esomeprazole attenuates inflammatory and fibrotic response in lung cells through the MAPK/Nrf2/HO1 pathway. J Inflamm (Lond). 2021 May 19;18(1):17. doi: 10.1186/s12950-021-00284-6. PMID: 34011367; PMCID: PMC8136131. 2. Xu Q, Jia X, Wu Q, Shi L, Ma Z, Ba N, Zhao H, Xia X, Zhang Z. Esomeprazole affects the proliferation, metastasis, apoptosis and chemosensitivity of gastric cancer cells by regulating lncRNA/circRNA-miRNA-mRNA ceRNA networks. Oncol Lett. 2020 Dec;20(6):329. doi: 10.3892/ol.2020.12193. Epub 2020 Oct 6. PMID: 33101498; PMCID: PMC7577076.
In vivo protocol:	1. Xie W, Huang X, Chen R, Chen R, Li T, Wu W, Huang Z. Esomeprazole alleviates the damage to stress ulcer in rats through not only its antisecretory effect but its antioxidant effect by inactivating the p38 MAPK and NF-κB signaling pathways. Drug Des Devel Ther. 2019 Aug 22;13:2969-2984. doi: 10.2147/DDDT.S193641. PMID: 31686780; PMCID: PMC6709796. 2. Pham N, Ludwig MS, Wang M, Ebrahimpour A, Bonnen MD, Diwan AH, Kim SJ, Bryan J, Newton JM, Sikora AG, Donovan DT, Sandulache V, Ghebre YT. Topical Esomeprazole Mitigates Radiation-Induced Dermal Inflammation and Fibrosis. Radiat Res. 2019 Nov;192(5):473-482. doi: 10.1667/RR15398.1. Epub 2019 Aug 15. PMID: 31415221; PMCID: PMC6876297.

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1: Baker DE. Esomeprazole magnesium (Nexium). Rev Gastroenterol Disord. 2001;1(1):32-41. PMID: 12120118.

2: Qi Q, Wang R, Liu L, Zhao F, Wang S. Comparative effectiveness and tolerability of esomeprazole and omeprazole in gastro-esophageal reflux disease: A systematic review and meta-analysis. Int J Clin Pharmacol Ther. 2015 Oct;53(10):803-10. doi: 10.5414/CP202396. PMID: 26329348.

3: Yang E, Kim S, Kim B, Kim B, Kim Y, Park SS, Song GS, Yu KS, Jang IJ, Lee S. Night-time gastric acid suppression by tegoprazan compared to vonoprazan or esomeprazole. Br J Clin Pharmacol. 2022 Jul;88(7):3288-3296. doi: 10.1111/bcp.15268. Epub 2022 Feb 23. PMID: 35146797; PMCID: PMC9305887.

4: Skieneh J, Khalili Najafabadi B, Horne S, Rohani S. Crystallization of Esomeprazole Magnesium Water/Butanol Solvate. Molecules. 2016 Apr 23;21(4):544. doi: 10.3390/molecules21040544. PMID: 27120591; PMCID: PMC6273358.

5: Gu S, Zhou C, Pei J, Wu Y, Wan S, Zhao X, Hu J, Hua X. Esomeprazole inhibits hypoxia/endothelial dysfunction-induced autophagy in preeclampsia. Cell Tissue Res. 2022 Apr;388(1):181-194. doi: 10.1007/s00441-022-03587-z. Epub 2022 Jan 29. PMID: 35091806; PMCID: PMC8976802.

6: Bi H, Chen X, Chen Y, Zhao X, Wang S, Wang J, Lyu T, Han S, Lin T, Li M, Yuan D, Liu J, Shi Y. Efficacy and safety of high-dose esomeprazole-amoxicillin dual therapy for Helicobacter pylori rescue treatment: a multicenter, prospective, randomized, controlled trial. Chin Med J (Engl). 2022 Jul 20;135(14):1707-1715. doi: 10.1097/CM9.0000000000002289. PMID: 36193978; PMCID: PMC9509165.

7: Lee KN, Lee OY, Chun HJ, Kim JI, Kim SK, Lee SW, Park KS, Lee KL, Choi SC, Jang JY, Kim GH, Sung IK, Park MI, Kwon JG, Kim N, Kim JJ, Lee ST, Kim HS, Kim KB, Lee YC, Choi MG, Lee JS, Jung HY, Lee KJ, Kim JH, Chung H. Randomized controlled trial to evaluate the efficacy and safety of fexuprazan compared with esomeprazole in erosive esophagitis. World J Gastroenterol. 2022 Nov 28;28(44):6294-6309. doi: 10.3748/wjg.v28.i44.6294. PMID: 36504556; PMCID: PMC9730436.

8: Esomeprazole magnesium. Am J Health Syst Pharm. 2002 Jan 15;59(2):127-9. PMID: 11826566.

9: Jankowski JAZ, de Caestecker J, Love SB, Reilly G, Watson P, Sanders S, Ang Y, Morris D, Bhandari P, Brooks C, Attwood S, Harrison R, Barr H, Moayyedi P; AspECT Trial Team. Esomeprazole and aspirin in Barrett's oesophagus (AspECT): a randomised factorial trial. Lancet. 2018 Aug 4;392(10145):400-408. doi: 10.1016/S0140-6736(18)31388-6. Epub 2018 Jul 26. Erratum in: Lancet. 2018 Dec 15;392(10164):2552. PMID: 30057104; PMCID: PMC6083438.

10: Sakurai Y, Mori Y, Okamoto H, Nishimura A, Komura E, Araki T, Shiramoto M. Acid-inhibitory effects of vonoprazan 20 mg compared with esomeprazole 20 mg or rabeprazole 10 mg in healthy adult male subjects--a randomised open-label cross- over study. Aliment Pharmacol Ther. 2015 Sep;42(6):719-30. doi: 10.1111/apt.13325. Epub 2015 Jul 21. PMID: 26193978.

11: Shafik AN, Khattab MA, Osman AH. Magnesium sulfate versus esomeprazole impact on the neonates of preeclamptic rats. Eur J Obstet Gynecol Reprod Biol. 2018 Jun;225:236-242. doi: 10.1016/j.ejogrb.2018.05.004. Epub 2018 May 8. PMID: 29758543.

12: Boinpally R, Lu K. Evaluation of the Pharmacokinetic Interaction and Safety of Ubrogepant Coadministered With Esomeprazole Magnesium. Clin Pharmacol Drug Dev. 2022 Feb;11(2):270-277. doi: 10.1002/cpdd.1034. Epub 2021 Nov 22. PMID: 34811955.

13: Zhong XF, Zhou G, Xu SM, Li XM, Xu Y, Liu WL, Zhang YX, He LC, Shen QY, Xu PS. Pharmacokinetics of Esomeprazole Magnesium After Single Oral Doses in Healthy Subjects: Bioequivalence Study and Food Effects. Clin Pharmacol Drug Dev. 2022 Nov;11(11):1308-1313. doi: 10.1002/cpdd.1139. Epub 2022 Jul 13. PMID: 35822412.

14: Ebrahimpour A, Ahir M, Wang M, Jegga AG, Bonnen MD, Eissa NT, Montesi SB, Raghu G, Ghebre YT. Combination of esomeprazole and pirfenidone enhances antifibrotic efficacy in vitro and in a mouse model of TGFβ-induced lung fibrosis. Sci Rep. 2022 Nov 30;12(1):20668. doi: 10.1038/s41598-022-24985-x. PMID: 36450789; PMCID: PMC9712660.

15: Naproxen/esomeprazole (Vimovo). Med Lett Drugs Ther. 2010 Sep 20;52(1347):74-5. PMID: 20847717.

16: Keating GM, Figgitt DP. Intravenous esomeprazole. Drugs. 2004;64(8):875-82; discussion 883. doi: 10.2165/00003495-200464080-00008. PMID: 15059043.

17: Chiang HC, Yang EH, Hu HM, Chen WY, Chang WL, Wu CT, Wu DC, Sheu BS, Cheng HC. An extended 36-week oral esomeprazole improved long-term recurrent peptic ulcer bleeding in patients at high risk of rebleeding. BMC Gastroenterol. 2022 Oct 21;22(1):439. doi: 10.1186/s12876-022-02534-0. PMID: 36271335; PMCID: PMC9585769.

18: Abdo-Francis JM, Cabrera-Álvarez G, Martínez-Torres H, Remes-Troche JM. Efficacy and safety comparative study of dexrabeprazole vs. esomeprazole for the treatment of gastroesophageal reflux disease. Gac Med Mex. 2022;158(6):423-429. English. doi: 10.24875/GMM.M22000722. PMID: 36657136.

19: de Alwis N, Fato BR, Beard S, Binder NK, Kaitu'u-Lino TJ, Onda K, Hannan NJ. Assessment of the Proton Pump Inhibitor, Esomeprazole Magnesium Hydrate and Trihydrate, on Pathophysiological Markers of Preeclampsia in Preclinical Human Models of Disease. Int J Mol Sci. 2022 Aug 23;23(17):9533. doi: 10.3390/ijms23179533. PMID: 36076929; PMCID: PMC9455231.

20: Nieves JW, Perez MC, Metz DC, Hansen KE. Reply. Gastroenterology. 2019 Aug;157(2):586. doi: 10.1053/j.gastro.2019.06.006. Epub 2019 Jun 13. PMID: 31260666.

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