Rimonabant

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

What is the Rimonabant?

The molecule Rimonabant presents a molecular formula of C₂₂H₂₁Cl₃N₄O and its IUPAC name is 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide.

Rimonabant (INN, trade name Acomplia) is an anorectic antiobesity drug developed by Sanofi-Aventis. Rimonabant is also known as SR141716; its original developmental code name was SR141613. It was the first selective CB1 receptor blocker to be marketed..

Rimonabant was first approved in Europe in 2006 under the trade name Acomplia® by the European Medicines Agency (EMEA) for the treatment of obesity. The drug was subsequently rejected for approval by the United States Food and Drug Administration (FDA) in 2007. In October 2008, the FDA's Endocrinologic and Metabolic Drugs Advisory Committee (EMDAC) voted unanimously not to recommend approval of rimonabant for marketing in the United States. The FDA cited concerns about rimonabant's psychiatric side effects..

Rimonabant is an inverse agonist of the cannabinoid receptor CB1. It was developed for the treatment of obesity and related conditions, and acts by reducing hunger cravings. Rimonabant binds to the same brain receptors as the active ingredient in cannabis (THC), but instead of producing the "high" associated with marijuana use, rimonabant actually reduces the desire for food..

In clinical trials, rimonabant was shown to be effective in helping obese patients lose weight and keep it off. Rimonabant was also shown to help patients with type 2 diabetes improve their blood sugar control and reduce their waist size..

However, rimonabant has also been linked with a number of serious side effects, including depression, anxiety, and suicidal thoughts. For these reasons, the FDA has not approved rimonabant for use in the United States..

3D structure

Cartesian coordinates

Geometry of Rimonabant 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.