Fulvestrant (S enantiomer)

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

What is the Fulvestrant (S enantiomer)?

The molecule Fulvestrant (S enantiomer) presents a molecular formula of C32H47F5O3S and its IUPAC name is (7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-[(S)-4,4,5,5,5-pentafluoropentylsulfinyl]nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol.

Fulvestrant is a molecule that belongs to a class of drugs known as selective estrogen receptor degraders (SERDs). Fulvestrant is the S enantiomer of the racemic mixture of fulvestrant. The other enantiomer is R-fulvestrant..

Fulvestrant was originally developed by AstraZeneca. It is approved by the US Food and Drug Administration (FDA) for the treatment of hormone receptor-positive breast cancer in postmenopausal women. It is also approved in Europe for the treatment of hormone receptor-positive breast cancer in both pre- and postmenopausal women..

Fulvestrant works by binding to and degrading the estrogen receptor (ER) in breast cancer cells. This leads to the downregulation of ER-dependent genes, which leads to the growth arrest and death of breast cancer cells..

Fulvestrant has been shown to be effective in the treatment of hormone receptor-positive breast cancer that is resistant to other anti-estrogen therapies, such as tamoxifen. Fulvestrant is typically given as an injection into the buttock once per month..

The most common side effects of fulvestrant include hot flashes, joint pain, fatigue, and nausea. Fulvestrant can also cause serious side effects, such as liver damage, so it is important to talk to your doctor about the risks and benefits of this medication before starting treatment..

3D structure

Cartesian coordinates

Geometry of Fulvestrant (S enantiomer) in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Fulvestrant (S enantiomer) VWUXBMIQPBEWFH-GXZKXCMSSA-N chemical compound 2D structure molecule svg
Fulvestrant (S enantiomer)

 

Molecule descriptors

 
IUPAC name(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-[(S)-4,4,5,5,5-pentafluoropentylsulfinyl]nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
InChI codeInChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-,27+,28+,29-,30+,41+/m1/s1
InChI KeyVWUXBMIQPBEWFH-GXZKXCMSSA-N
SMILESC[C@]12CC[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCCCCC[S@](=O)CCCC(F)(F)C(F)(F)F)[C@H]3[C@@H]1CC[C@@H]2O

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.

  • BDBM50556030
  • CS-8169
  • Fulvestrant (S enantiomer)
  • HY-13636A

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3926298
  • CHEMBL4760678

Physico-Chemical properties

IUPAC name(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-[(S)-4,4,5,5,5-pentafluoropentylsulfinyl]nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Molecular formulaC32H47F5O3S
Molecular weight606.771
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity156.93
LogP9.5
Topological polar surface area76.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow 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(Kow) (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 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.