Pantoprazole Chemical Properties

Melting point:

139-140° (dec)

Boiling point:

586.9±60.0 °C(Predicted)

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)

pka

pKa1 3.92; pKa2 8.19(at 25℃)

form 

Solid

color 

Off-White to Pale Orange

BCS Class

3

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

SMILES

C1(S(CC2=NC=CC(OC)=C2OC)=O)NC2=CC(OC(F)F)=CC=C2N=1

CAS DataBase Reference

102625-70-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-37/38-41-48

Safety Statements 

22-26-36/37/39-45

Hazardous Substances Data

102625-70-7(Hazardous Substances Data)

Pantoprazole Usage And Synthesis

Description

Pantoprazole, an irreversible proton pump inhibitor, reached its first market worldwide in Germany for acute treatment of gastric and duodenal ulcers and gastroesophageal reflux disease. Proton pump inhibitors are more effective than other strategies in inhibiting acid secretion since they function at the final step of acid production, therefore, provide superior symptom relief and healing in all acid related diseases. As the third substituted benzimidazole proton pump inhibitor marketed, pantoprazole not only has superior ulcer-preventing effect but also is more potent than omeprazole in healing acetic acid-induced gastric and duodenal ulcers with extremely low acute toxicity. The mechanism of action for this class of compounds has been suggested to be mediated via the protonated form of the molecule which selectively reacts with cysteines present on the extracytoplasmic face of the enzyme to form covalent disulfide bonds.

Originator

Byk Gulden (Germany)

Uses

proton pump inhibitor, gastric acid release inhibitor, antiulcer

Definition

ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.

Manufacturing Process

2-Chloromethyl-4,5-dimethoxy-3-methylpyridinium chloride (about 1.5 g) are added to a solution of 5-difluoromethoxy-1H-benzimidazole-2-thiol in 10 ml of ethanol and 10 ml of 1 N sodium hydroxide solution. The yellow reaction mixture is stirred at 20°C for 1 hour, a further 10 ml of water are added, whereupon a colorless solid precipitates out, the mixture is stirred for a further 5 hours and filtered and the residue is rinsed with 1 N sodium hydroxide solution and water and dried to constant weight. The 5difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole is obtained as an oil.
5-Difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole (about 1 g) are dissolved in 10 ml of dioxane and 2 ml of 1 N sodium hydroxide solution. An equimolar amount of a titrated aqueous sodium hypochlorite solution, to which 1 mole per liter of sodium hydroxide solution has been added, is first added dropwise, while cooling with ice. After one hour a further equivalent and after 3 hours half the equimolar amount of sodium hypochlorite are added, to achieve complete reaction. After a reaction time of 4 hours, 5 ml of 5% strength sodium thiosulfate solution and another 25 ml of dioxane are added and the upper dioxane phase is separated off, washed once with 5 ml of sodium thiosulfate solution and concentrated on a rotary evaporator. The oily residue is dissolved in 20 ml of water and 10 ml of ethyl acetate and the solution is brought to pH 7 with about 100 ml of a buffer solution of pH 6.8. The solid which has precipitated out is filtered off with suction over a suction filter, washed with water, extracted by stirring at 0C with acetone and dried. 5-Difluoromethoxy-2-[(4,5-dimethoxy-2pyridyl)methanesulfinyl]-1H-benzimidazole is prepared; yield about 85%.

brand name

Pantozol; Rifun

Therapeutic Function

Antiulcer

Clinical Use

Pantoprazole

Veterinary Drugs and Treatments

Pantoprazole may be useful in treating or preventing gastric acidrelated pathologies in dogs, cats, foals and camelids, particularly when the intravenous route is preferred. Pantoprazole is available in both intravenous and oral tablet (delayed-release) formulations. One study (Bersenas, Mathews et al. 2005) performed in dogs, comparing the gastric pH effects of intravenous pantoprazole with oral omeprazole, intravenous ranitidine, and intravenous famotidine, found at the dosages used, that pantoprazole was more effective than ranitidine, but similar to famotidine, and that oral omeprazole was more effective in maintaining intragastric pH >3 for a longer period than pantoprazole.
Pantoprazole has been shown to directly reduce in vitro counts of H. pylori and is used in some H. pylori treatment protocols for humans.

Drug interactions

Potentially hazardous interactions with other drugs
Anticoagulants: effect of coumarins possibly enhanced.
Antifungals: absorption of itraconazole and ketoconazole reduced; avoid with posaconazole.
Antivirals: concentration of atazanavir and rilpivirine reduced - avoid; concentration of raltegravir and saquinavir possibly increased - avoid.
Clopidogrel: possibly 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.

Metabolism

Pantoprazole is extensively metabolised in the liver, primarily by the cytochrome P450 isoenzyme CYP2C19, to desmethylpantoprazole; small amounts are also metabolised by CYP3A4, CYP2D6, and CYP2C9.
Metabolites are excreted mainly in the urine, with the remainder being excreted in faeces via the bile.

References

[1] jungnickel p w. pantoprazole: a new proton pump inhibitor. clinical therapeutics, 2000, 22(11): 1268-1293.
[2] sachs g, shin j m, howden c w. review article: the clinical pharmacology of proton pump inhibitors. alimentary pharmacology & therapeutics, 2006, 23(s2): 2-8.

Pantoprazole(102625-70-7)Related Product Information

• 4-Methoxybenzyl alcohol
• 4-Methoxybenzyl cyanide
• p-Anisidine
• (Trifluoromethoxy)benzene
• 4-Methoxyphenol
• Guaiacol
• Anisole
• p-Anisaldehyde
• Pantoprazole Sodium
• 4-Methoxybenzoic acid
• PANTOPRAZOLE SULPHONE SODIUM SALT
• Rabeprazole
• Omeprazole
• R-(+)-Lansoprazole
• 5-Difluoromethoxy-2-mercapto-1H-Benzimidazole(Pantoprazole Intermediate
• Intermediate of pantoprazole sodium
• 2-chloromethyl-3,4-dimethoxy pyridine HCL (intermediate of pantoprazole),Pantoprazole Intermediate
• 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE