Esomeprazole

Names

[ CAS No. ]:
119141-88-7

[ Name ]:
Esomeprazole

[Synonym ]:
S-enantiomer of omeprazole
Nexium
esomeprazolum
(-)-Omeprazole
(S)-(-)-Omeprazole
1H-Benzimidazole, 5-methoxy-2-[(S)-[(1S)-(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-
Esomeprazole (INN)
perprazole
(S)-Omeprazole
MFCD06798050
EINECS 201-212-8
6-Methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole
[14C]-(-)-Omeprazole
1H-Benzimidazole, 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-
(S)-6-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
Esomeprazole
5-Methoxy-2-{(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl}-1H-benzimidazole
esomeprazol
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
(S)-Esomeprazole
UNII-N3PA6559FT
6-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole

Biological Activity

[Description]:

Esomeprazole ((S)-Omeprazole) is a potent and orally active proton pump inhibitor and reduces acid secretion through inhibition of the H+, K+-ATPase in gastric parietal cells. Esomeprazole has the potential for symptomatic gastroesophageal reflux disease research[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Endocrinology

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump

[Target]

H+, K+-ATPase[1][2]

[In Vitro]

Esomeprazole (25-100 µM; 20 hours; MDA-MB-468 cells) treatment suppresses growth of triple-negative breast cancer cell in vitro in a dose-dependent manner through increase in their intracellular acidification[1]. Cell Viability Assay[1] Cell Line: MDA-MB-468 cells Concentration: 25 µM, 50 µM, 75 µM, 100 µM Incubation Time: 20 hours Result: Suppressed growth of triple-negative breast cancer cell in vitro in a dose-dependent manner.

[In Vivo]

Esomeprazole (30-300 mg/kg; oral gavage; daily; for 19 or 11 days; C57BL/6J mice) treatment significantly inhibits the progression of fibrosis throughout the lungs of the animals. Esomeprazole also reduces circulating markers of inflammation and fibrosis[2]. Animal Model: C57BL/6J mice (8-weeks old, 25-30 g) treated with cotton smoke-induced lung injury[2] Dosage: 30 mg/kg, 300 mg/kg Administration: Oral gavage; daily; for 19 or 11 days Result: Significantly inhibited the progression of fibrosis throughout the lungs of the animals.

[References]

[1]. Wayne Goh, et al. Use of proton pump inhibitors as adjunct treatment for triple-negative breast cancers. An introductory study. J Pharm Pharm Sci. 2014;17(3):439-46.

[2]. Christina Nelson, et al. Therapeutic Efficacy of Esomeprazole in Cotton Smoke-Induced Lung Injury Model. Front Pharmacol. 2017 Jan 26;8:16.

[3]. Thomas J Johnson, et al. Esomeprazole: a clinical review. Am J Health Syst Pharm. 2002 Jul 15;59(14):1333-9.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
600.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₁₉N₃O₃S

[ Molecular Weight ]:
345.416

[ Flash Point ]:
316.7±32.9 °C

[ Exact Mass ]:
345.114716

[ PSA ]:
96.31000

[ LogP ]:
2.17

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.669

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%