Dexrabeprazole

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Dexrabeprazole are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Dexrabeprazole?

The molecule Dexrabeprazole presents a molecular formula of C₁₈H₂₁N₃O₃S and its IUPAC name is 2-[(R)-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-benzimidazole.

Dexrabeprazole (INN, USAN, BAN) (brand names Aciphex, Pariet, Dexilant) is a proton pump inhibitor (PPI) of the substituted benzimidazole class. It is used in the treatment of gastroesophageal reflux disease (GERD), Helicobacter pylori infections, and erosive esophagitis. It was patented in 1987 and approved for medical use in 1995..

Dexrabeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the hydrogen-potassium adenosine triphosphatase enzyme system of the gastric parietal cells. By inhibiting this enzyme, dexrabeprazole reduces gastric acid secretion..

The efficacy of dexrabeprazole in the healing of erosive esophagitis has been demonstrated in four 8-week, multicenter, randomized, double-blind, placebo-controlled studies in adult patients. In these studies, dexrabeprazole 20 mg and 40 mg were significantly more effective than placebo in healing erosive esophagitis..

The healing rates of dexrabeprazole 20 mg and 40 mg were similar in these studies. The time to healing (defined as the number of days to endoscopically confirmed healing) was also similar between the two dexrabeprazole treatment groups..

In a randomized, double-blind, placebo-controlled study in pediatric patients 1 to 11 years of age with GERD, dexrabeprazole 10 mg or 20 mg once daily for 4 weeks was significantly more effective than placebo in healing erosive esophagitis..

In a long-term, open-label study, adult patients with symptomatic GERD and healed erosive esophagitis who continued treatment with dexrabeprazole 20 mg or 40 mg once daily for up to 1 year had a low incidence of symptomatic relapse of GERD..

The safety and efficacy of dexrabeprazole have been evaluated in pediatric patients 1 to 16 years of age in two 8-week, multicenter, randomized, double-blind, placebo-controlled studies and in a long-term, open-label study. In the 8-week studies, dexrabeprazole 10 mg or 20 mg once daily was significantly more effective than placebo in healing erosive esophagitis..

The healing rates of dexrabeprazole 10 mg and 20 mg were similar in these studies. The time to healing (defined as the number of days to endoscopically confirmed healing) was also similar between the two dexrabeprazole treatment groups..

In the long-term, open-label study, pediatric patients with symptomatic GERD and healed erosive esophagitis who continued treatment with dexrabeprazole 10 mg or 20 mg once daily for up to 1 year had a low incidence of symptomatic relapse of GERD..

The safety and tolerability of dexrabeprazole in pediatric patients 1 to 11 years of age were similar to those in adults. In the 8-week, placebo-controlled studies in pediatric patients, the most common adverse reactions (> 3% and more common on dexrabeprazole than on placebo) were headache (5.5% vs 2.8%), diarrhea (5.1% vs 2.8%), and abdominal pain (3.6% vs 1.4%)..

In the long-term, open-label study, the most common adverse reactions (> 5% and more common on dexrabeprazole than on placebo) were headache (8.6% vs 2.8%), diarrhea (7.1% vs 2.8%), and flatulence (5.7% vs 1.4%)..

The safety and tolerability of dexrabeprazole in pediatric patients 12 to 16 years of age were similar to those in adults. In the 8-week, placebo-controlled studies in pediatric patients, the most common adverse reactions (> 5% and more common on dexrabeprazole than on placebo) were headache (8.0% vs 2.3%), diarrhea (6.7% vs 1.7%), and abdominal pain (5.3% vs 2.3%)..

In the long-term, open-label study, the most common adverse reactions (> 5% and more common on dexrabeprazole than on placebo) were headache (8.6% vs 2.8%), diarrhea (7.1% vs 2.8%), and flatulence (5.7% vs 1.4%)..

The safety and efficacy of dexrabeprazole have been evaluated in two 8-week, multicenter, randomized, double-blind, placebo-controlled studies in adult patients with GERD. In these studies, dexrabeprazole 20 mg and 40 mg were significantly more effective than placebo in.

3D structure

Cartesian coordinates

Geometry of Dexrabeprazole in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Molecule descriptors

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

• CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
• Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
• ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
• PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
• RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
• ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
• CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

Physico-Chemical properties

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Ų are required. Thus, molecules with a polar surface area greater than 140 Ų tend to be poorly permeable to cell membranes.