2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

• ChemBase ID: 331
• Molecular Formular: C16H14F3N3O2S
• Molecular Mass: 369.3614696
• Monoisotopic Mass: 369.07588236
• SMILES: S(=O)(Cc1nccc(OCC(F)(F)F)c1C)c1[nH]c2c(n1)cccc2
• Canonical SMILES: O=S(c1nc2c([nH]1)cccc2)Cc1nccc(c1C)OCC(F)(F)F
• InChI: InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
• InChIKey: MJIHNNLFOKEZEW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC Traditional name: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole; lansoprazole
• Brand Name: Agopton; Amarin; Aprazol; Bamalite; Biuret; Biuret Gr; Biuret Reagent; Biuret Reagent Solution; Blason; Compraz; Dakar; Ilsatec; Ketian; Lancid; Lanproton; Lansopep; Lansoprazol [INN-Spanish]; Lansoprazole [Usan:Ban:Inn]; Lansoprazolum [INN-Latin]; Lanston; Lanz; Lanzol-30; Lanzopral; Lanzor; Lasoprol; Limpidex; Mesactol; Monolitum; Ogast; Ogastro; Opiren; Prevacid; Prevacid Iv; Prevacid Solutab; Prevpac; Prezal; Pro Ulco; Promp; Prosogan; Suprecid; Takepron; Ulpax; Zoprol; Zoton
• Synonyms: lansoprazole; AG 1749; Lansoprazole; 2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; A-65006; AG-1749; Agopton; Lansox; Lanzor; Limpidex; Ogast; 2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; Dexlansoprazole; R-(+)-Lansoprazole; T 168390; TAK 390; (R)-Lansoprazole; Bamalite; Lanzo; Prezal; Takepron; Zoton; 2-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methylsulfinyl)-1h-benzoimidazole; Prevacid; Prevacid NapraPAC; Prevacid SoluTab; Lansoprazole; 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole

Database IDs

• CAS Number: 103577-45-3; 138530-94-6
• MDL Number: MFCD00866873
• PubChem SID: 160963794; 24278520; 46508975
• PubChem CID: 3883

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.34671
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.013967
• LogD (pH = 7.4): 3.0283315
• Log P: 3.0328553
• Molar Refractivity: 87.608 cm^3
• Polarizability: 34.145214 Å^3
• Polar Surface Area: 67.87 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.84
• LOG S: -3.17
• Solubility (Water): 2.50e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.97 mg/L; Chloroform; Methanol
• Apperance: Brown Solid; off-white powder; White Solid
• Melting Point: 178-182°C dec.; 66-68°C
• Hydrophobicity(logP): 1.9

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Hygroscopic, Refrigerator, Under inert atmosphere
• Storage Warning: Hygroscopic
• RTECS: DD9487500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Proton pump
• Mechanism of Action: H-K ATPASE inhibitor; Proton pump inhibitor

Product Information

• Purity: ≥98% (TLC); 97%
• Salt Data: Free Base
• Application(s): Used as an antiulcerogenic agent for duodenal ulcers and gastroesophageal reflux disease

DETAILS

DrugBank - DB00448

• Drug Groups: approved; investigational
• Description: Lansoprazole is a proton pump inhibitor which prevents the stomach from producing acid. It is manufactured by TAP Pharmaceutical Products. Lansoprazole has been marketed for many years and is one of several PPI's available.
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
• Pharmacology: Lansoprazole, an acid proton-pump inhibitor similar to omeprazole, is used as an untiulcer drug in the treatment and maintenance of healing of duodenal or gastric ulcers, erosive and reflux esophagitis, NSAID-induced ulcer, Zollinger-Ellison syndrome, and Barrett's esophagus. Lansoprozole is active against Helicobacter pylori. The plasma elimination half-life of lansoprazole does not reflect its duration of suppression of gastric acid secretion. Thus, the plasma elimination half-life is less than two hours, while the acid inhibitory effect lasts more than 24 hours.
• Toxicity: Symptoms of overdose include abdominal pain, nausea and diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Two metabolites have been identified in measurable quantities in plasma (the hydroxylated sulfinyl and sulfone derivatives of lansoprazole). These metabolites have very little or no antisecretory activity. Lansoprazole is thought to be transformed into two active species which inhibit acid secretion by (H^+,K^+)-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation.
• Absorption: The absorption of lansoprazole is rapid, with mean C_max occurring approximately 1.7 hours after oral dosing, and relatively complete with absolute bioavailability over 80%.
• Half Life: 1.5 (± 1.0) hours
• Protein Binding: 97%
• Elimination: Following single-dose oral administration of PREVACID, virtually no unchanged lansoprazole was excreted in the urine. In one study, after a single oral dose of 14C-lansoprazole, approximately one-third of the administered radiation was excreted in the urine and two-thirds was recovered in the feces. This implies a significant biliary excretion of the lansoprazole metabolites.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1354

Research Area: Liver cancer
Biological Activity:
Lansoprazole is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid.It is used to treat duodenal and gastric ulcers, erosive esophagitis, and gastroesophageal reflux disease (GERD). Lansoprazole is also used to treat Zollinger-Ellison syndrome (ZES), which is a condition where the stomach produces too much acid. [1]

Sigma Aldrich - L8533

Biochem/physiol Actions
Gastric proton pump inhibitor.

Toronto Research Chemicals - L175000

Used as a gastric proton pump inhibitor. An antiulcerative.

Toronto Research Chemicals - L175010

The R-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative.

REFERENCES

• http://www.rxlist.com/prevacid-drug.htm
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• Figgitt, D., et al.: Drugs, 60, 925 (2000)
• Katsuki, H., et al.: Eur. J. Clin. Pharmacol., 57, 709 (2000)
• Barradell, L.B., et al.: Drugs, 44, 225 (2000)
• Kim, K., et al.: Clin. Pharmacol. Ther., 72, 90 (2000)
• Niioka, T., et al.: Ther. Drug Monit., 28, 3
• Eur. Pat., 1986, 174 726; CA, 105, 133883, (synth, pharmacol)
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• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1196