Mestranol

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

What is the Mestranol?

The molecule Mestranol presents a molecular formula of C₂₁H₂₆O₂ and its IUPAC name is (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol.

Mestranol is a synthetic estrogen that was first introduced in the 1950s. It is a prodrug of ethinylestradiol, meaning that it is converted into ethinylestradiol (EE) in the body. Mestranol is no longer used as a medication on its own, but it is still found in some combination oral contraceptives..

Mestranol is a white, crystalline powder that is insoluble in water. It has a molecular weight of 290.4 and a molecular formula of C20H24N2O2..

When mestranol is ingested, it is converted into ethinylestradiol by first-pass metabolism in the liver. Ethinylestradiol is the active estrogen in the body. It binds to and activates estrogen receptors, which leads to the various effects of estrogen..

The main difference between mestranol and other estrogens is that mestranol is a prodrug of ethinylestradiol. This means that it is converted into ethinylestradiol in the body. Mestranol is no longer used as a medication on its own, but it is still found in some combination oral contraceptives..

Mestranol has a long history of use as a medication. It was first introduced in the 1950s and was used for a variety of indications, including menopausal hormone therapy and contraception..

Mestranol is no longer used as a standalone medication, but it is still found in some combination oral contraceptives. These oral contraceptives contain a combination of an estrogen (usually ethinylestradiol) and a progestin (usually norethindrone)..

The combination of an estrogen and a progestin is more effective at preventing pregnancy than either medication alone. The progestin in the oral contraceptive works to prevent ovulation, while the estrogen works to thicken the mucus in the cervix, making it more difficult for sperm to reach the egg..

The side effects of mestranol are similar to those of other estrogens. The most common side effects are nausea, vomiting, bloating, breast tenderness, and headaches. These side effects are usually mild and resolve with time..

Mestranol is a synthetic estrogen that was first introduced in the 1950s. It is a prodrug of ethinylestradiol, meaning that it is converted into ethinylestradiol (EE) in the body. Mestranol is no longer used as a medication on its own, but it is still found in some combination oral contraceptives..

3D structure

Cartesian coordinates

Geometry of Mestranol 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.