Esomeprazole

Base Information

• Chemical Name: Esomeprazole
• CAS No.: 119141-88-7
• Deprecated CAS: 193469-77-1,326602-80-6,1116141-00-4,177541-03-6,177541-03-6,326602-80-6
• Molecular Formula: C17H19N3O3S
• Molecular Weight: 345.422
• Hs Code.: 29339900
• UNII: N3PA6559FT
• DSSTox Substance ID: DTXSID4044292
• Wikipedia: Esomeprazole
• Wikidata: Q553223
• NCI Thesaurus Code: C65538
• RXCUI: 283742,1601995
• Pharos Ligand ID: 32AV3B2YL85T
• Metabolomics Workbench ID: 38698
• ChEMBL ID: CHEMBL1201320
• Mol file: 119141-88-7.mol

Synonyms:Esomeprazole;Esomeprazole Magnesium;Esomeprazole Potassium;Esomeprazole Sodium;Esomeprazole Strontium;Esomeprazole Strontium Anhydrous;Nexium;Strontium, Esomeprazole

Chemical Property of Esomeprazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.669
• Boiling Point: 599.991 °C at 760 mmHg
• PKA: 8.50±0.10(Predicted)
• Flash Point: 316.663 °C
• PSA: 96.31000
• Density: 1.371 g/cm³
• LogP: 3.76540
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 345.11471265
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

99.5% ^*data from raw suppliers

(S)-6-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole tech. ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
• Isomeric SMILES: CC1=CN=C(C(=C1OC)C)C[S@](=O)C2=NC3=C(N2)C=C(C=C3)OC
• Recent ClinicalTrials: A Study to Evaluate the Efficacy and Safety of Tegoprazan in GERD Patients With Nighttime Heartburn
• Recent EU Clinical Trials: 'A Phase III Study to Assess the Efficacy and Safety of NEXIUM for Maintenance of Healing of Erosive Esophagitis in Pediatric Patients 1 to 11 Years of Age'
• Recent NIPH Clinical Trials: V-POINT study
• Description: Esomeprazole, formulated as a magnesium salt, reached the market as a treatment for acid-related diseases such as gastro-esophageal reflux (GERD) disease including peptic ulcer disease and reflux esophagitis. Esomeprazole (formerly perprazole) is the active (S)- enantiomer of omeprazole (1988) and the first proton pump inhibitor developed as an optical isomer. It can be obtained by several routes such as asymmetric oxidation of the pro-chiral pyridylmethyl benzimidazole sulfide, separation from the racemic sulfoxide by chiral chromatography or separation of a diastereomeric mixture obtained from the racemic compound and a chiral acid, followed by hydrolysis. Biochemical studies have shown that esomeprazole irreversibly inhibits the gastric H+/K+-adenosine triphosphatase (ATPase), an enzyme system involved at the secretory surface of the stomach’s parietal cells responsible for the secretion of gastric acid. Compared with racemic omeprazole in healthy subjects, esomeprazole has higher bioavailability, is absorbed more rapidly and exhibits a more uniform and predictable dose-response with higher plasma levels, leading to less inter-individual variability between slow and rapid metabolizers. In extensive clinical trials in patients suffering from GERD symptoms, esomeprazole provided superior acid control and significantly reduced the healing time compared to omeprazole.
• Uses: (-)-Omeprazole can be used to treat migraine. Esomeprazole is used to treat certain stomach and esophagus problems (such as acid reflux, ulcers). ?It works by decreasing the amount of acid your stomach makes. It ?relieves symptoms such as heartburn, difficulty swallowing, and ?persistent cough.
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugsAnticoagulants: effect of coumarins possibly enhanced.Antiepileptics: effects of fosphenytoin and phenytoin enhanced.Antifungals: absorption of itraconazole and ketoconazole reduced; avoid with posaconazole; concentration possibly increased by voriconazole.Antivirals: concentration of atazanavir and rilpivirine reduced - avoid concomitant use; concentration of raltegravir and saquinavir possibly increased - avoid; concentration of esomeprazole reduced by tipranavir.Clopidogrel: reduced antiplatelet effect.Cytotoxics: possibly reduced excretion of methotrexate; avoid with dasatinib, erlotinib and vandetanib; possibly reduced lapatinib absorption; possibly reduced absorption of pazopanib.Ulipristal: reduced contraceptive effect, avoid with high dose ulipristal

Technology Process of Esomeprazole

There total 50 articles about Esomeprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

omeprazole sulfide (73590-85-9) → esomeprazole (119141-88-7)

Guidance literature:

omeprazole sulfide; With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; In water; toluene; at 65 - 70 ℃; for 0.833333h;

With Cumene hydroperoxide; N-ethyl-N,N-diisopropylamine; In water; toluene; at 2 - 5 ℃;

Reference yield: 99.0%

S-omeprazole*(S)-[1.1'-binaphthalen]-2.2'-diol inclusion complex → esomeprazole (119141-88-7)

Guidance literature:

With sodium hydroxide; In water; toluene; pH=11.5 - 12.0; Product distribution / selectivity;

Reference yield: 98.0%

(S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole [(S)-1,1,2-triphenyl-1,2-ethanediol]2 → esomeprazole (119141-88-7)

Guidance literature:

(S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole [(S)-1,1,2-triphenyl-1,2-ethanediol]2; With sodium hydroxide; In water; toluene; at 80 ℃;

With acetic acid; In water; toluene; at 0 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

omeprazole

omeprazole sulfide

(S)-5-methoxy-2-[[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

sodium methylate

Downstream raw materials:

(S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole (R)-1-cyclohexylethyl ammonium salt

(S)-6-methoxy-1-benzyloxycarbonyl-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

(S)-5-methoxy-1-benzyloxycarbonyl-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Refernces

• 1、 Talsi, Evgenii P.,Bryliakov, Konstantin P.. "Ti-Salan catalyzed asymmetric sulfoxidation of pyridylmethylthiobenzimidazoles to optically pure proton pump inhibitors". . p. 84 - 89. Retrieved 2017.
• 2、 Seenivasaperumal, Muthu,Federsel, Hans-Juergen,Ertan, Anne,Szabo, Kalman J.. "Factors influencing the selectivity in asymmetric oxidation of sulfides attached to nitrogen containing heterocycles". . p. 2187 - 2189. Retrieved 2007.
• 3、 Song, Weiguo,Dong, Liangjun,Zhou, Yuhan,Fu, Yongqiang,Xu, Wenfang. "Catalytic Asymmetric Synthesis of Esomeprazole by a Titanium Complex with a Hexa-aza-triphenolic Macrocycle Ligand". . p. 70 - 77. Retrieved 2015.
• 4、 Bong, Yong Koy,Song, Shiwei,Nazor, Jovana,Vogel, Michael,Widegren, Magnus,Smith, Derek,Collier, Steven J.,Wilson, Rob,Palanivel,Narayanaswamy, Karthik,Mijts, Ben,Clay, Michael D.,Fong, Ryan,Colbeck, Jeff,Appaswami, Amritha,Muley, Sheela,Zhu, Jun,Zhang, Xiyun,Liang, Jack,Entwistle, David. "Baeyer-Villiger Monooxygenase-Mediated Synthesis of Esomeprazole As an Alternative for Kagan Sulfoxidation". . p. 7453 - 7458. Retrieved 2018.
• 5、 Deng, Jingen,Chi, Yongxiang,Fu, Fangmin,Cui, Xin,Yu, Kaibai,Zhu, Jin,Jiang, Yaozhong. "Resolution of omeprazole by inclusion complexation with a chiral host BINOL". . p. 1729 - 1732. Retrieved 2000.
• 6、 Reddy, Lekkala Amarnath,Malakondaiah, Golla China,Babu, Karrothu Srihari,Bhattacharya, Apurba,Bandichhor, Rakeshwar,Himabindu, Vimmidi,Reddy, Padi Pratap,Anand, Ramasamy Vijaya. "An investigation on key parameters that influence the resolution of omeprazole sodium". . p. 66 - 68. Retrieved 2008.
• 7、 Lin, Guo-Qiang,Wu, Yin-Qi,Xia, Jian-Ye,Xu, Jian-He,Xu, Na,Yu, Hui-Lei,Zhang, Yan,Zhao, Qian,Zhu, Jun. "Enzymatic Preparation of the Chiral (S)-Sulfoxide Drug Esomeprazole at Pilot-Scale Levels". . p. 1124 - 1130. Retrieved 2020.
• 8、 -. "Synthetic method of esomeprazole". Paragraph 0017; 0026-0027; 0031; 0034; 0037-0038; 0042;.... . Retrieved 2021/11/27.