Lansoprazole

Base Information

• Chemical Name: Lansoprazole
• CAS No.: 103577-45-3
• Molecular Formula: C16H14F3N3O2S
• Molecular Weight: 369.367
• Hs Code.: 29339900
• European Community (EC) Number: 627-144-2,645-308-1
• NSC Number: 758710,758638
• UNII: 0K5C5T2QPG
• DSSTox Substance ID: DTXSID4023200
• Nikkaji Number: J126.212B
• Wikipedia: Lansoprazole
• Wikidata: Q254296
• NCI Thesaurus Code: C29150
• RXCUI: 17128
• Pharos Ligand ID: SSKC1L3KYBS7
• Metabolomics Workbench ID: 38697
• ChEMBL ID: CHEMBL480
• Mol file: 103577-45-3.mol

Synonyms:2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methyl)sulfinyl)benzimidazole;AG 1749;AG-1749;AG1749;Agopton;Bamalite;Lansol;lansoprazol;lansoprazole;Lansoprazole Sodium;Lansoprazoles;Lanzor;Monolitum;Ogast;Ogastro;Opiren;Prevacid;Prezal;Pro Ulco;Promeco;Sodium, Lansoprazole;Takepron;Ulpax;Zoton

Chemical Property of Lansoprazole

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.55E-10mmHg at 25°C
• Melting Point: 178-182 °C
• Refractive Index: 1.591
• Boiling Point: 555.8 °C at 760 mmHg
• PKA: pKa 2.34±0.37 (Occasionally);3.53±0.37 (Occasionally);8.48±0.30 (Occasionally)
• Flash Point: 289.9 °C
• PSA: 87.08000
• Density: 1.5 g/cm³
• LogP: 4.38090
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in anhydrous ethanol, very slightly soluble in acetonitrile.
• 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:

99.5% ^*data from raw suppliers

Lansoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiulcer Agents
• Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
• Recent ClinicalTrials: A Proof of Concept Window Trial of the IMmunological Effects of AveLumab and Aspirin in Triple-Negative Breast Cancer
• Recent EU Clinical Trials: A randomized double-blind, double dummy, active comparator-controlled dose finding study in patients with reflux esophagitis Los Angeles grade C or D, and patients with at least partial symptom response but endoscopically still unhealed after 8 weeks history of standard treatment healing course with proton-pump inhibitor (PPI), to investigate safety, tolerability, and healing rates after 4 weeks treatment of X842 or lansoprazole, and symptom pattern during subsequent 4 weeks treatment with lansoprazole
• Recent NIPH Clinical Trials: Multicenter randomized crossover study about Every Second Day administration of Vonoprazan for the maintenance treatment of erosive GERD (ESD-Von-GERD)
• Uses: Lansoprazole is a proton pump inhibitor (PPI) similar to omeprazole that inactivates the hydrogen/potassium-stimulated ATPase pumps in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a potent inhibitor of gastric acidity which is widely used in the therapy of gastroesophageal reflux and peptic ulcer disease. Lansoprazole is a racemic mixture of (R)- and (S)-isomers. Dexlansoprazole is an isomer of lansoprazole that has a similar spectrum of activity and toxicities. Lansoprazole therapy is associated with a low rate of transient and asymptomatic serum aminotransferase elevations and is a reported, but very rare cause of clinically apparent liver injury. Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects (i. e. gastric acid suppression). The plasma elimination half-life is 1. 5 hours or less, and the effects of the drug last for over 24 hours after it has been given for 5 days or more. Lansoprazole is a prescription medicine used to treat: gastroesophageal reflux disease (GERD) erosive esophagitis stomach ulcers duodenal ulcers H. Pylori infections Zollinger-Ellison syndrome A H+,K+-ATPase inhibitor that displays antisecretory activity Treatment of gastroesophageal reflux disease (GERD), erosive esophagitis, duodenal ulcers, Helicobacter pylori (H. pylori) infections,stomach ulcers, prevention of stomach ulcers in those people taking non-steroidal anti-inflammatory drugs (NSAIDs), such For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use. Used as a gastric proton pump inhibitor. An antiulcerative
• Drug interactions: 1. Take R-(+)-Lansoprazole in conjunction with acetaminophen can increase the Peak blood concentration and shorten the time to peak. 2. Take R-(+)-Lansoprazole in conjunction with Roxithromycin can increase the local concentration of the latter and has a synergistic effect when treating Hp infection. 3. Take R-(+)-Lansoprazole in conjunction with antacids can reduce the bioavailability of this product. If necessary, this product should be taken after 1 hour use of antacids. 4. Take R-(+)-Lansoprazole in conjunction with theophylline can slightly reduce the? blood concentrations of theophylline. 5. R-(+)-Lansoprazole can inhibit gastric acid secretion significantly and persistently, thereby reduce the absorption of itraconazole and ketoconazole. So they should not be used at the same time. 6. Sucralfate may interfere the absorption of this product and reduce its bioavailability. So this product should be taken at least 30 minutes before taking sucralfate. 7. Take R-(+)-Lansoprazole in conjunction with clarithromycin may cause? Glossitis, stomatitis and black tongue. Patients should pay attention to the change of oral mucosa , stop using clarithromycin and reduce the dose of this product if necessary.
• Description: Lansoprazole is a proton pump inhibitor that inhibits the H+/K+-ATPase. It inhibits K+ and H+ accumulation in gastric microsomes in a concentration-dependent manner (IC50s = 6.3 and 7.0 μM, respectively) and inhibits H+/K+-ATPase activity by approximately 60% when used at a concentration of 10 μM. Lansoprazole inhibits the H+/K+-ATPase in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a substituted benzimidazole that binds covalently to proton pumps, providing complete and prolonged inhibition of acid secretion. Formulations containing lansoprazole have been used as a proton pump inhibitor and in combination with antibiotics in the treatment of H. pylori infections and duodenal ulcer disease. Lansoprazole is the second proton pump inhibitor approved as an antiulcer agent for the short term treatment of duodenal ulcer and gastroesophageal reflux disease. Like omeprazole, lansoprazole is reported to be more efficacious than the H2-antagonists in treating peptic ulcer disease.Other potential uses could be in the treatment of Zollinger-Ellison syndrome.
• Therapeutic Function: Antiulcer

Technology Process of Lansoprazole

There total 33 articles about Lansoprazole 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%

lansoprazole sulfide (103577-40-8) → lansoprasole (103577-45-3)

Guidance literature:

With 2C₅H₈N₂*VO₂F; dihydrogen peroxide; In ethanol; at 10 - 15 ℃; for 2h; Temperature; Industrial scale;

Reference yield: 98.0%

3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride + Benzimidazol-2-thiol (134469-07-1) → lansoprasole (103577-45-3)

Guidance literature:

3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride; Benzimidazol-2-thiol; With carboxy chlorine; sodium carbonate; In methanol; at 64 ℃; for 3h;

With titanium(IV) isopropylate; In water; toluene; at 28 - 55 ℃; for 1.83333h; Temperature; Solvent; Reagent/catalyst; Further stages;

Reference yield: 95.2%

lansoprazole hydrate acetonitrile solvate → lansoprasole (103577-45-3)

Guidance literature:

With ammonia; In water; acetonitrile; at 0 - 40 ℃; for 3.5h; Product distribution / selectivity;

upstream raw materials:

lansoprazole sulfide

2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole

2,3-dimethyl-4-nitropyridine N-oxide

2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine

Downstream raw materials:

N-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenyl)urea

1-[{2-(morpholin-4-yl)ethoxy}phenyl-4-sulfonyl]-2-[(3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methylsulfinyl]-1H-benzimidazole

2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}-phenoxy)-N-(2-pyridyl)acetamide

N-(carbamoylmethyl)-2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide

Refernces

• 1、 Arreguin-Espinosa, Roberto,Calderón-Jaimes, Ernesto,Cuevas-Cruz, Miguel,Gómez-Manzo, Saúl,Hernández-Ochoa, Beatriz,Méndez-Tenorio, Alfonso,Marcial-Quino, Jaime,Ramírez-Nava, Edson Jiovany,Rocha-Ramírez, Luz María,Sánchez-Carrillo, Adrián,Santos-Segura, Araceli. "Enhanced Antigiardial Effect of Omeprazole Analog Benzimidazole Compounds". . . Retrieved 2020/09/18.
• 2、 -. "Method for preparing benzimidazole proton pump inhibitor". Paragraph 0049; 0050; 0051; 0053; 0054; 0055; 0056-0058. . Retrieved 2018/09/08.