Dexlansoprazole

Base Information

• Chemical Name: Dexlansoprazole
• CAS No.: 138530-94-6
• Molecular Formula: C16H14F3N3O2S
• Molecular Weight: 369.367
• European Community (EC) Number: 688-930-9
• UNII: UYE4T5I70X
• Wikipedia: Dexlansoprazole
• Wikidata: Q5268339
• NCI Thesaurus Code: C73192
• RXCUI: 816346
• Pharos Ligand ID: SSKHG6YF1VN6
• Metabolomics Workbench ID: 149449
• ChEMBL ID: CHEMBL1201863
• Mol file: 138530-94-6.mol

Synonyms:2-((R)-((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole;dexilant;dexlansoprazole;Dexlansoprazole Sesquihydrate;Lansoprazole, R Isomer;Lansoprazole, R-Isomer;R Lansoprazole;R-Isomer Lansoprazole;R-Lansoprazole;T 168390;T-168390;T168390;TAK 390;TAK 390MR;TAK-390;TAK-390MR;TAK390;TAK390MR

Chemical Property of Dexlansoprazole

Chemical Property:

• Appearance/Colour: Brown solid
• Melting Point: 66-68?C
• Boiling Point: 555.8±60.0 °C(Predicted)
• PKA: 9.56±0.10(Predicted)
• PSA: 87.08000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: 4.38090
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 369.07588236
• Heavy Atom Count: 25
• Complexity: 480

Purity/Quality:

99%, ^*data from raw suppliers

(R)-Lansoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
• Isomeric SMILES: CC1=C(C=CN=C1C[S@@](=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
• Recent ClinicalTrials: A Study of Dexlansoprazole in Healing and Maintenance of Healed Erosive Esophagitis (EE) in Children
• Recent EU Clinical Trials: A Phase 2, Double Blind, Up to 40 Week, Multicenter Study to Assess the Safety and
• Description: The mechanism of PPIs involves the irreversible binding to the hydrogen/potassium adenosine triphosphatase enzyme system, commonly referred to as the gastric proton pump, of the gastric parietal cell. As the last stage in gastric acid secretion, blockade of the gastric proton pump is an effective treatment for a variety of diseases requiring acid suppression, such as heartburn, peptic ulcers, and GERD. Dexlansoprazole is the latest PPI to hit the market, joining the ranks of omeprazole, rabeprazole, pantoprazole, esomeprazole, and lansoprazole, and is the Renantiomer of the racemic lansoprazole. Compared to its predecessors, dexlansoprazole exhibits improved pharmacokinetics with slower clearance and longer terminal half-life. In addition, dexlansoprazole utilizes a novel DDR technology; drug release is optimized through the use of granules with different pH-dependent dissolution profiles, thereby providing an initial release in the proximal small intestine within 1-2 h of administration followed by a subsequent release at distal regions of the small intestine several hours later. With its longer duration of action culminating in more effective acid suppression, dexlansoprazole may have an advantage over conventional PPIs that possess single release formulations (immediate or delayed). Similar to all PPIs, dexlansoprazole is a prodrug that consists of pyridine and benzimidazole rings with a latent sulfenamide moiety. In order to form the disulfide bond with cysteine residues of the proton pump, dexlansoprazole must be activated through two protonations followed by a spontaneous rearrangement to unmask the sulfenamide. Lansoprazole is a proton pump inhibitor that irreversibly inactivates the H+/K+-stimulated ATPase pumps in parietal cells, inhibiting gastric acid secretion and increasing intragastric pH. It is a 1:1 racemic mixture of (R)-lansoprazole and (S)-lansoprazole, both of which are pharmacologically active. (R)-Lansoprazole is an enantiomerically pure form of lansoprazole. It can inhibit acid formation in isolated canine parietal cells with an IC50 value of 59 nM and inhibit the H+/K+-ATPase with an IC50 value of 4.2 μM.
• Uses: antiulcer, proton pump inhibitor Acts as a gastric proton pump inhibitor and an antiulcerative The R-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative
• Clinical Use: Takeda Pharmaceuticals received approval of dexlansoprazole, a dual release formulation of the (R)-isomer of lansoprazol proton pump inhibitor (PPI) already in the market, from the FDA in January 2009. Dexlansoprazole is a delayed release capsule for the oncedaily, oral treatment of heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD), the healing of erosive esophagitis (EE) and the maintenance of healed EE. The dual release formulation is designed to provide two separate releases of medication, one at 1–2 h and then another at 4–5 h after treatment, for extended efficacy in the treatment of GERD.

Technology Process of Dexlansoprazole

There total 21 articles about Dexlansoprazole 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: 100.0%

R-lansoprazole 0.5 hydrate → (R)-lansoprazole (138530-94-6)

Guidance literature:

at 70 ℃; for 6h; Product distribution / selectivity;

Reference yield: 100.0%

(R)-2-[[[3-methyl-4-(2,2,2-trifluoroetoxy)-2-piridyl]methyl]sulphinyl]benzimidazole sesquihydrate → (R)-lansoprazole (138530-94-6)

Guidance literature:

at 65 ℃; for 7 - 8h; Product distribution / selectivity;

Reference yield: 91.0%

(R)-(+)-lansoprazole (R)-(+)-1,1,2-triphenyl-1,2-ethanediol complex → (R)-lansoprazole (138530-94-6)

Guidance literature:

(R)-(+)-lansoprazole (R)-(+)-1,1,2-triphenyl-1,2-ethanediol complex; With potassium hydroxide; In dichloromethane; water;

With hydrogenchloride; In dichloromethane; water; ethyl acetate; pH=7;

upstream raw materials:

lansoprazole sulfide

lansoprasole

(R)-(+)-2-(3-methyl-4-nitropyridin-2-ylmethansulfinyl)-1H-benzimidazole

2,2,2-trifluoroethanol

Downstream raw materials:

isopropyl 1-[(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazol-l-yl] ethyl carbonate

2-[[4-(aminocarbonyl)phenyl] [[(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl]amino]ethyl acetate

2-[methyl[[(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl]amino]ethyl 4-trifluoromethoxybenzoate

2-[methyl[[(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl]amino]ethyl 3,4,5-trimethoxybenzoate

Refernces

• 1、 -. "Method for preparing dexlansoprazole through catalysis of hexadentate ligand". Paragraph 0046; 0048-0049; 0051. . Retrieved 2020/05/30.
• 2、 -. "Dexlansoprazole single crystal, and preparation method and application thereof". Paragraph 0018-0023. . Retrieved 2018/07/07.