Dimercaprol, (S)-

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

What is the Dimercaprol, (S)-?

The molecule Dimercaprol, (S)- presents a molecular formula of C₃H₈OS₂ and its IUPAC name is (2S)-2,3-bis(sulfanyl)propan-1-ol.

Dimercaprol, also known as British anti-lewisite (BAL), is an organoarsenic compound used as an antidote for arsenic, gold, and mercury poisoning, and has also been investigated for use as a cancer treatment. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Dimercaprol exists as a generic medication and is not very expensive..

The mechanism of action of dimercaprol is not fully understood, but it is thought to work by chelation of metals. It is given by intramuscular injection..

Common side effects include nausea, vomiting, headache, and rashes. Dimercaprol is in pregnancy category C and so should only be used when the potential benefit justifies the potential risk to the fetus. It is a chelating agent and as such can bind to essential minerals such as iron and copper, which can lead to anemia and other problems..

Dimercaprol was first synthesized in 1937 by British chemist Bernard Henry Collin as a potential antineoplastic agent. However, it was found to be ineffective against cancer. In 1940, it was found to be an effective treatment for arsenic, gold, and mercury poisoning, and it has been used for this purpose since then..

Dimercaprol is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Dimercaprol exists as a generic medication and is not very expensive..

3D structure

Cartesian coordinates

Geometry of Dimercaprol, (S)- 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.