(S)-Sulindac

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

What is the (S)-Sulindac?

The molecule (S)-Sulindac presents a molecular formula of C20H17FO3S and its IUPAC name is 2-[(3Z)-6-fluoro-2-methyl-3-[[4-[(S)-methylsulfinyl]phenyl]methylidene]inden-1-yl]acetic acid.

Sulindac (INN) is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid family, related to other NSAIDs such as indomethacin, naproxen, and tofenacin. It is marketed under the brand names Clinoril and Sulamyd..

Sulindac is used to treat mild to moderate pain, inflammation, and fever. It is also used to reduce the risk of colorectal cancer in people with familial adenomatous polyposis..

The mechanism of action of sulindac is not completely understood, but it is thought to work by inhibiting the synthesis of prostaglandins, molecules that play a role in pain and inflammation..

Sulindac is generally well-tolerated, but side effects can include gastrointestinal upset, dizziness, and rashes. More serious but rare side effects can include liver damage and kidney failure..

Sulindac is a prescription drug and should be used only as directed by a healthcare provider..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-Sulindac MLKXDPUZXIRXEP-WXKFDZDZSA-N chemical compound 2D structure molecule svg
(S)-Sulindac

 

Molecule descriptors

 
IUPAC name2-[(3Z)-6-fluoro-2-methyl-3-[[4-[(S)-methylsulfinyl]phenyl]methylidene]inden-1-yl]acetic acid
InChI codeInChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-/t25-/m0/s1
InChI KeyMLKXDPUZXIRXEP-WXKFDZDZSA-N
SMILESCC1=C(CC(=O)O)c2cc(F)ccc2/C1=C\c1ccc([S@](C)=O)cc1

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.

  • (S)-Sulindac
  • 149116-77-8
  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-((S)-methylsulfinyl)phenyl)methylene)-, (1Z)-
  • 2-[(3Z)-6-fluoro-2-methyl-3-[[4-[(S)-methylsulfinyl]phenyl]methylidene]inden-1-yl]acetic acid
  • P969C405OM
  • Q26998355
  • S-Sulindac Sulfoxide
  • S-sulindac
  • Sulindac, (S)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4475353
  • UNII-P969C405OM
  • CHEMBL3527054
  • SCHEMBL487717
  • SCHEMBL15700834

Physico-Chemical properties

IUPAC name2-[(3Z)-6-fluoro-2-methyl-3-[[4-[(S)-methylsulfinyl]phenyl]methylidene]inden-1-yl]acetic acid
Molecular formulaC20H17FO3S
Molecular weight356.411
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity98.35
LogP5.2
Topological polar surface area73.6

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.