6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

• ChemBase ID: 98
• Molecular Formular: C16H15F2N3O4S
• Molecular Mass: 383.3698064
• Monoisotopic Mass: 383.07513342
• SMILES: S(=O)(c1[nH]c2c(n1)ccc(OC(F)F)c2)Cc1nccc(OC)c1OC
• Canonical SMILES: COc1c(OC)ccnc1CS(=O)c1nc2c([nH]1)cc(cc2)OC(F)F
• InChI: InChI=1S/C16H15F2N3O4S/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16/h3-7,15H,8H2,1-2H3,(H,20,21)
• InChIKey: IQPSEEYGBUAQFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
• IUPAC Traditional name: 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole
• Brand Name: Pantoloc; Protonix; Protonix I.V.; Protonix IV; Pantopan; Protium; Pantozol; Pantor; Astropan
• Synonyms: Pantoprazol [INN-Spanish]; Pantoprazole Na; Pantoprazole Sodium; Pantoprazolum [INN-Latin]; Pantoprozole; Pantoprazole

Database IDs

• CAS Number: 102625-70-7
• PubChem SID: 46504622; 160963561
• PubChem CID: 4679

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.152253
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.170947
• LogD (pH = 7.4): 2.169018
• Log P: 2.1757534
• Molar Refractivity: 90.052 cm^3
• Polarizability: 35.872173 Å^3
• Polar Surface Area: 86.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.11
• LOG S: -2.89
• Solubility (Water): 4.95e-01 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble in water.
• Hydrophobicity(logP): 0.5

DETAILS

DrugBank - DB00213

• Drug Groups: approved
• Description: Pantoprazole is a proton pump inhibitor drug used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease.
• Indication: Short-term (up to 16 weeks) treatment of erosive esophagitis.
• Pharmacology: Pantoprazole is a substituted benzimidazole indicated for the short-term treatment (up to 16 weeks) in the healing and symptomatic relief of erosive esophagitis. Pantoprazole is a proton pump inhibitor (PPI) that suppresses the final step in gastric acid production.
• Toxicity: Single intravenous doses of pantoprazole at 378, 230, and 266 mg/kg (38, 46, and 177 times the recommended human dose based on body surface area) were lethal to mice, rats and dogs, respectively. The symptoms of toxicity included hypoactivity, ataxia, hunched sitting, limb-splay, lateral position, segregation, absence of ear reflex, and tremor. There is limited experience regarding cases of human overdosage, and treatment should be symptomatic and supportive.
• Affected Organisms: Humans and other mammals
• Biotransformation: Pantoprazole is extensively metabolized in the liver through the cytochrome P450 (CYP) system. The main metabolic pathway is demethylation, by CYP2C19, with subsequent sulfation; other metabolic pathways include oxidation by CYP3A4. There is no evidence that any of the pantoprazole metabolites have significant pharmacologic activity.
• Absorption: Pantoprazole is well absorbed. It undergoes little first-pass metabolism resulting in an absolute bioavailability of approximately 77%.
• Half Life: 1 hour
• Protein Binding: 98%
• Elimination: After administration of a single intravenous dose of 14C-labeled pantoprazole to healthy, normal metabolizer subjects, approximately 71% of the dose was excreted in the urine with 18% excreted in the feces through biliary excretion.
• Distribution: * 11.0 to 23.6 L
• Clearance: * 7.6-14.0 L/h
• External Links: Wikipedia; RxList; Drugs.com