Pantoprazole

Common name: Pantoprazole; Protonix; Pantoprazolum; Pantozol; Pantoprazole Sodium; BY-1023; Pantoloc

Trademarks: Pantazone; Pantop-D; Pantasan; Pantrol; Prazolin; Pantochem; Pansev; Pantec; Somac; Pantecta; Pantoloc

Molecular Formula: C16H15F2N3O4S

CAS Registry Number: 102625-70-7

CAS Name: 6-(Difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole

Molecular Weight: 383.370

SMILES: COC1=C(OC)C(CS(=O)C2=NC3=C(N2)C=C(OC(F)F)C=C3)=NC=C1
InChI Key: IQPSEEYGBUAQFF-UHFFFAOYSA-N
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)

Activity: Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Esophageal Diseases, Gastric Antisecretory Drugs, Gastroesophageal Reflux Disease, GASTROINTESTINAL DRUGS, ABCC3 Expression Enhancers, H+/K+-ATPase Inhibitors

Pantoprazole as Medicine:

Pantoprazole is in a class of medications called proton-pump inhibitors (PPIs). It works by decreasing the amount of acid made in the stomach. Pantoprazole is used to treat gastroesophageal reflux disease (GERD), a condition in which backward flow of acid from the stomach causes heartburn and possible injury of the esophagus (the tube between the throat and stomach). It is also used to treat conditions where the stomach produces too much acid, such as Zollinger-Ellison syndrome.

Pantoprazole as Chemical Compound:

It is an organic heterocyclic compound having a Benzimidazole moiety. More specifically, it is a sulfinylbenzimidazoles - a polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety. Other important chemical classifications are:

1. Organoflourine compound

2. Alkyl aryl ethers 

3. Pyridines and derivatives 

4. Heteroaromatic compounds 

5. Sulfoxides 

6. Sulfinyl compounds 

7. Azacyclic compounds 

8. Alkyl fluorides

9. Flouromethane compounds

Pantoprazole synthesis: J Med Chem 1992, 35(6), 1049-57

Pantoprazole synthesis: WO2002028852A1

Important chemistry involved in Pantoprazole synthesis:

1. Flourine Chemistry

2. Acetylation Chemistry

3. Reduction Process

4. Oxidation Process

Common Side-Effects

Common side effects of Pantoprazole include headache, diarrhea, nausea, and abdominal pain. Moreover, these side-effects are also reported fast or uneven heart rate, diarrhea that is watery or bloody, muscle cramps, muscle weakness, memory problems, weakness, loss of appetite, feeling unsteady, confusion, hallucinations, fainting, seizure, or shallow breathing.

Two important observations:

1. The chronic use of Pantoprazole has caused stomach cancer in animal studies, but it is not known if this medication would have the same effects in humans.

2. Long-term treatment with Pantoprazole may also make it harder for your body to absorb vitamin B-12, resulting in a deficiency of this vitamin.

References:

1. Palomo, C. A.; A process for the preparation of pantoprazole and intermediates therefor. WO2002028852A1.

2. Kohl, B.; et. al. (H+,K+)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles. 4. A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity. The selection of pantoprazole as a clinical candidate. J Med Chem, 1992, 35(6), 1049-57.

3. Mathad, V. T.; et. al. An Improved and Single-Pot Process for the Production of Pantoprazole Substantially Free from Sulfone Impurity. Org Proc Res Dev, 2004, 8(2), 266–270.

4. Rainer, G. Dr.; et. al. Substituted pyridylmethylthio-(or sulfinyl-)benzimidazoles having a secretolytic activity. EP0134400A3

For more drugs and their synthesis: Synayurajan database