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Esomeprazole magnesium structure
Esomeprazole magnesium structure

Esomeprazole magnesium

Iupac Name:magnesium;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-ide
CAS No.: 161973-10-0
Molecular Weight:713.12100
Modify Date.: 2022-11-22 16:09
Introduction:

ChEBI: A magnesium salt resulting from the formal reaction of magnesium hydroxide with 2 mol eq. of esomeprazole. An inhibitor of gastric acid secretion, it is used for the treatment of gastro-oesophageal reflux disease, dyspepsia, peptic ulcer disease, and Zolli ger-Ellison syndrome.Esomeprazole magnesium,S-bis(5-rnethoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole-l-yl) magnesiumtrihydrate (Nexium), is the S-enantiomer ofomeprazole. The benzimidazole PPIs co


Magnesium 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]benzimidazol-1-ide is a member of benzimidazoles and a sulfoxide.|The S-isomer of omeprazole.

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1. Names and Identifiers
1.1 Name
Esomeprazole magnesium
1.2 Synonyms

(-)-Omeprazole magnesium (S)-Omeprazole magnesium (T-4-(S),(S))-Bis(5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazolato)magnesium (T-4)-Bis(5-methoxy-2-((S)-((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl-kO)-1H-benzimidazolato-kN1)magnesium (T-4)-bis[6-methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl-κO]-1H-benzimidazolato-κN3]-magnesium 1H-Benzimidazole, 5-methoxy-2-[(S)-[(1S)-(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, magnesium salt (2:1) 5-Methoxy-2-((S)-((4-Methoxy-3,5-diMethyl-2-pyridyl)Methyl)sulfinyl-1H-benziMidazole MagnesiuM salt Bis(5-methoxy-2-{(S)-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}benzimidazol-1-ide) magnesium EsMeprazole Magne-siuM Trihydrate Esomeprazole ESOMEPRAZOLE MAGNESIUM SAMPLE ESOMEPRAZOLE MAGNESIUM/SODIUM H 199/18 H-199/18 Magnesium 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-ide Magnesium bis(5-methoxy-2-{(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl}benzimidazol-1-ide) Magnesium bis(5-methoxy-2-{(S)-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}benzimidazol-1-ide) Magnesium bis{(6-methoxybenzimidazol-1-id-2-yl)[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfoniumolate} MagnesiuM,bis[6-Methoxy-2-[(S)-[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl-kO]-1H-benziMidazolato-kN3]-, (T-4)- Nexium omeprazole magnesium sulfonium, hydroxy(6-methoxy-1H-benzimidazol-2-yl)[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-, inner salt, magnesium salt (2:1)

1.3 CAS No.
161973-10-0
1.4 CID
130564
1.5 EINECS(EC#)
2017-001-1
1.6 Molecular Formula
C34H36MgN6O6S2 (isomer)
1.7 Inchi
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
1.8 InChkey
KWORUUGOSLYAGD-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC.CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC.[Mg+2]
1.10 Isomers Smiles
CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC.CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC.[Mg+2]
2. Properties
2.1 Boiling point
600ºC at 760 mmHg
2.1 Flash Point
316.7ºC
2.1 Precise Quality
712.19900
2.1 PSA
186.82000
2.1 logP
6.78900
2.1 Appearance
White to Light yellow powder to crystal
2.2 Chemical Properties
Esomeprazole is the S-isomer (enantiomer) of omeprazole, and the first PPI to be developed as an optical isomer. Similar to other PPIs, esomeprazole suppresses gastric acid secretion by inhibiting the parietal cell membrane enzyme, H+/K+-ATPase. Esomeprazole is rapidly degraded in acidic media but is stable under alkaline conditions just as all other PPIs are. Each capsule of esomeprazole magnesium contains enteric-coated granules to prevent esomeprazole degradation by gastric acidity. Esomeprazole, chemical name:(S)-5-methoxy-2-([(4-methoxy-3,5-dimethyl-2-pyridinyl) methyl]sulfinyl)-1H-benzimidazole, is a weak base. It is converted to its active form, a sulfenamide analog, in the acidic environment of the gastric parietal cell. It effectively blocks acid secretion by irreversibly binding to and inhibiting the enzyme H+/K+-ATPase that resides on the luminal surface of the parietal cell membrane, resulting in disulfide bond formation with cysteine 813 located within the α-subunit of the enzyme. This is the residue that is intimately involved in H+ transport. All PPIs are weak protonatable pyridines, with a pKa 4.0 for omeprazole, esomeprazole and lansoprazole, 3.9 for pantoprazole and 5.0 for rabeprazole. The rate of conversion varies among the compounds and is inversely proportional to their pKa: that is, rabeprazole> omeprazole/esomeprazole = lansoprazole> pantoprazole. As a result, they accumulate specifically and selectively in the secretory canaliculus, the highly acidic space, of the parietal cell[11]. Within that space, PPIs undergo an acid catalyzed conversion to become a reactive species, the thiophilic sulfenamide, which are permanent cations.
2.3 StorageTemp
Inert atmosphere,2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A magnesium salt resulting from the formal reaction of magnesium hydroxide with 2 mol eq. of esomeprazole. An inhibitor of gastric acid secretion, it is used for the treatment of gastro-oesophageal reflux disease, dyspepsia, peptic ulcer disease, and Zolliger-Ellison syndrome.
3.2 Usage
Antiulcerative
4. Safety and Handling
4.1 Hazard Declaration
H302
4.1 Caution Statement
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

H412 Harmful to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P273 Avoid release to the environment.

Response

none

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Uses
S-Form of Omeprazole. Gastric proton-pump inhibitor.
7.1 General Description
Esomeprazole magnesium,S-bis(5-rnethoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole-l-yl) magnesiumtrihydrate (Nexium), is the S-enantiomer ofomeprazole. The benzimidazole PPIs contain a chiral sulfuratom that form an enantiomeric pair that is stable andinsoluble under standard conditions. The S-isomer ofomeprazole has slightly greater PPI activity, and its intrinsicclearance is approximately three times lower thanthat of R-omeprazole (15 vs. 43μL/min). The lowerclearance of S-omeprazole is related to slower metabolicclearance by the CYP2C19 isozyme. Although Romeprazoleis primarily transformed to the 5-hydroxymetabolite, the S-isomer is metabolized by O-demethylationand sulfoxidation, which contribute little to intrinsicclearance.
7.2 Mesh
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)|Compounds that inhibit H(+)-K(+)-EXCHANGING ATPASE. They are used as ANTI-ULCER AGENTS and sometimes in place of HISTAMINE H2 ANTAGONISTS for GASTROESOPHAGEAL REFLUX. (See all compounds classified as Proton Pump Inhibitors.)
7.3 Use Classification
Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
7.4 Indications
Esomeprazole, a proton-pump inhibitor (PPI), is the S-isomer of omeprazole. Esomeprazole has FDA-approved labeling for use in the treatment of symptomatic gastroesophageal reflux disease (GERD), including healing and maintenance of healing of erosive esophagitis and as part of a triple-drug regimen for Helicobacter pylori infection.
7.5 Mode of action
Esomeprazole is potent inhibitors of the final common pathway for gastric acid secretion by gastric parietal cells. A weak base, esomeprazole concentrates in the acidic compartment of secretory canaliculus of the parietal cells where it undergoes an acid-catalyzed transformation to a tetracyclic achiral cationic sulfonamide[15]. Inhibition of the H+/K+-ATPase enzyme occurs when the sulfonamide reacts with specific cysteine, blocking the final step in acid production and leading to adose-dependent reduction of gastric acid secretion. The binding of esomeprazole to the proton pump is covalent and irreversible[16, 17].
7.6 Drug interaction
Esomeprazole inhibits gastric acid secretion, which interferes with the absorption of medications requiring an acid medium for absorption (e.g., itraconazole). Like omeprazole, esomeprazole is metabolized via CYP2C19 and CYP3A4. Esomeprazole may inhibit the CYP2C19 pathway, which could interfere with other medications metabolized via this pathway. A 45% decrease in the clearance of diazepam in patients also taking esomeprazole has been reported[3]. However, the clinical relevance of this and other potential interactions is unknown. There do not appear to be any clinically significant interactions with phenytoin, warfarin, quinidine, or clarithromycin[3]. Other medications metabolized by CYP2C19 include phenytoin, cyclophosphamide, and some tricyclic antidepressants. These could be involved in interactions with esomeprazole. The possibility of interactions should be kept in mind when esomeprazole is used concurrently with products metabolized by CYP2C19 that have a low therapeutic index.
7.7 Uses
Antiulcerative
7.8 Definition
ChEBI: A magnesium salt resulting from the formal reaction of magnesium hydroxide with 2 mol eq. of esomeprazole. An inhibitor of gastric acid secretion, it is used for the treatment of gastro-oesophageal reflux disease, dyspepsia, peptic ulcer disease, and Zolli ger-Ellison syndrome.
7.9 Brand name
Nexium (AstraZeneca).
8. Computational chemical data
  • Molecular Weight: 713.12100g/mol
  • Molecular Formula: C34H36MgN6O6S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 712.1988169
  • Monoisotopic Mass: 712.1988169
  • Complexity: 453
  • Rotatable Bond Count: 10
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 14
  • Topological Polar Surface Area: 163
  • Heavy Atom Count: 49
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 3
  • CACTVS Substructure Key Fingerprint: AAADcfB/uABgACAAAAAAAAAAAAAAAWLAAAA8eIEAAAAAAFgB/gAAHgQAAAAADAzF3ga/1rYIFAqgAzRnZEDK2C1xMrAJ2CA+fJiMbuLkuZuUMChuwBvI6CewUAMOAEAAAgAAACAAgAAEAAAAQAAAAAAAAA==
9. Question & Answer
  • Esomeprazole is the S-isomer (enantiomer) of omeprazole, and the first PPI to be developed as an optical isomer. Similar to other PPIs, esomeprazole suppresses gastric acid secretion by inhibiting the parietal cell membrane enzyme, H+/K+-ATPase. Esomeprazole is rapidly degraded in acidic media but ...
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