Dapsone

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

What is the Dapsone?

The molecule Dapsone presents a molecular formula of C₁₂H₁₂N₂O₂S and its IUPAC name is 4-(4-aminophenyl)sulfonylaniline.

Dapsone is a sulfone antimicrobial agent with a white to off-white colour, and a crystalline powder with a molecular weight of 248.29 g/mol..

Dapsone is a bacteriostatic agent that inhibits the synthesis of dihydrofolic acid in bacteria by inhibiting the enzyme dihydropteroate synthase. This results in the inhibition of DNA synthesis and cell growth in susceptible bacteria. Dapsone is active against a wide range of bacteria, including Mycobacterium tuberculosis and Mycobacterium leprae, as well as some protozoa and fungi..

Dapsone is usually administered orally in the form of tablets, although it can also be given intravenously. It is rapidly absorbed from the gastrointestinal tract and is widely distributed throughout the body. Dapsone is metabolized in the liver and is eliminated mainly through the urine. The half-life of dapsone is about 12-24 hours..

Dapsone is used to treat a variety of infections, including tuberculosis, leprosy, and pneumocystis pneumonia. It is also sometimes used in the treatment of dermatitis herpetiformis, a chronic skin condition, and in combination with other drugs to treat malaria..

While dapsone is generally well tolerated, it can cause a number of side effects, including nausea, vomiting, dizziness, and headache. It can also cause a rare but serious side effect called methemoglobinemia, in which the level of methemoglobin in the blood increases, leading to a reduction in the oxygen-carrying capacity of the blood. This can cause symptoms such as shortness of breath, fatigue, and cyanosis (bluish discoloration of the skin)..

Summary

From all the above, this molecule is a useful antimicrobial agent that is used to treat a variety of infections. However, it should be used with caution due to the potential for side effects..

3D structure

Cartesian coordinates

Geometry of Dapsone 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.