Mifepristone

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

What is the Mifepristone?

The molecule Mifepristone presents a molecular formula of C₂₉H₃₅NO₂ and its IUPAC name is (8S,11R,13S,14S,17S)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one.

Mifepristone is a synthetic steroid molecule with both antiprogestational and antiglucocorticoid properties. It is a progesterone receptor antagonist and a glucocorticoid receptor agonist. Mifepristone was first synthesized in 1980 and was originally known as RU-486. It was developed as an antiprogestational agent for use in contraception and abortion. Mifepristone is currently approved for use in the United States for the medical termination of pregnancy up to 70 days gestation..

Mifepristone is a white to off-white powder that is insoluble in water. The molecular weight is 429.6 and the molecular formula is C29H35NO2. The structure of mifepristone is shown in Figure 1..

Mifepristone binds to the progesterone receptor (PR) with high affinity and specificity. It is a competitive antagonist of progesterone at the PR and inhibits the binding of progesterone to the receptor. Mifepristone also binds to the glucocorticoid receptor (GR) and is a weak agonist of the receptor. The binding of mifepristone to the GR results in the inhibition of cortisol binding to the receptor..

Mifepristone has a number of effects in the body that result in the termination of pregnancy. Mifepristone inhibits the secretion of progesterone by the corpus luteum, which is necessary for the maintenance of pregnancy. Mifepristone also inhibits the production of cortisol, which is necessary for the development of the fetal lung. In addition, mifepristone inhibits the production of prostaglandins, which are necessary for the maintenance of pregnancy..

Mifepristone is administered orally as a single dose of 200 mg. The recommended dose of mifepristone for the termination of pregnancy is 600 mg. Mifepristone is also available in a vaginal insert form..

Mifepristone is generally well tolerated. The most common side effects are nausea, vomiting, diarrhea, fatigue, and headache. Mifepristone is contraindicated in women with a history of hypersensitivity to the drug..

Mifepristone is a safe and effective option for the termination of pregnancy. Mifepristone is associated with a lower risk of complications than surgical abortion. Mifepristone is also associated with a lower risk of future fertility than surgical abortion..

3D structure

Cartesian coordinates

Geometry of Mifepristone 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.