trans-Ketoconazole

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

What is the trans-Ketoconazole?

The molecule trans-Ketoconazole presents a molecular formula of C₂₆H₂₈Cl₂N₄O₄ and its IUPAC name is 1-[4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone.

Trans-ketoconazole is a synthetic antifungal drug used to treat a variety of fungal infections. It is a member of the azole class of antifungals. Trans-ketoconazole was first synthesized in 1979 and approved for medical use in the United States in 1981..

Trans-ketoconazole inhibits the fungal enzyme 14α-demethylase, which participes in the biosynthesis of ergosterol, a key component of the fungal cell membrane. By inhibiting 14α-demethylase, trans-ketoconazole prevents the synthesis of ergosterol and other sterols required for fungal cell membrane function. This leads to the accumulation of 14α-methyl sterols in the fungal cell, which are toxic and cause the cell to rupture..

Trans-ketoconazole is active against a variety of fungal infections, including candidiasis, cryptococcosis, histoplasmosis, and dermatophytoses. It is also effective against some yeast infections, such as candida albicans. In addition to its antifungal activity, trans-ketoconazole has also been shown to have anti-inflammatory, immunomodulatory, and anticancer activity..

Trans-ketoconazole exists as a cream, gel, lotion, shampoo, and tablet. It is typically used for skin infections and scalp infections. For other infections, it is usually given as an oral tablet. Trans-ketoconazole is generally well-tolerated, but side effects can include nausea, vomiting, diarrhea, and abdominal pain. Rare but serious side effects include liver damage, kidney damage, and adrenal insufficiency..

Trans-ketoconazole is a potent antifungal drug with a wide range of activities. It is generally well-tolerated, but can cause serious side effects in some people..

3D structure

Cartesian coordinates

Geometry of trans-Ketoconazole 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.