Ceritinib

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

What is the Ceritinib?

The molecule Ceritinib presents a molecular formula of C₂₈H₃₆ClN₅O₃S and its IUPAC name is 5-chloro-2-N-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine.

Ceritinib (LDK378) is a drug used to treat non-small cell lung cancer (NSCLC). It is a kinase inhibitor that targets the anaplastic lymphoma kinase (ALK) protein. Ceritinib was approved by the United States Food and Drug Administration (FDA) in April 2014, and by the European Medicines Agency (EMA) in June 2014..

Ceritinib was developed by the pharmaceutical company Novartis. The drug was originally designed to treat ALK-positive NSCLC, a subtype of NSCLC that represents around 5% of all NSCLC cases. In clinical trials, ceritinib was found to be effective in treating ALK-positive NSCLC that had progressed after treatment with crizotinib, another ALK inhibitor..

Ceritinib exists in the United States as a 150 mg tablet. The recommended dose is 750 mg once daily. Ceritinib should be taken on an empty stomach, at least 1 hour before or 2 hours after a meal..

Common side effects of ceritinib include diarrhea, nausea, vomiting, fatigue, and decreased appetite. Ceritinib can also cause QT prolongation, a condition that can lead to irregular heartbeats..

Ceritinib is a potent and specific inhibitor of the ALK protein. In preclinical studies, ceritinib was found to inhibit the growth of ALK-positive NSCLC cell lines. Ceritinib has also been shown to cross the blood-brain barrier, which is important for the treatment of brain metastases..

Ceritinib is the first ALK inhibitor to be approved for the treatment of NSCLC. Clinical trials have shown that ceritinib is effective in treating ALK-positive NSCLC that has progressed after treatment with crizotinib. Ceritinib is generally well tolerated, with the most common side effects being diarrhea, nausea, vomiting, and fatigue..

3D structure

Cartesian coordinates

Geometry of Ceritinib 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.