Sulindac sulfide

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

What is the Sulindac sulfide?

The molecule Sulindac sulfide presents a molecular formula of C20H17FO2S and its IUPAC name is 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid.

Sulindac sulfide is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid class that is marketed under the brand names Clinoril and Sulindac. It is the sulfide derivative of sulindac. It is used to treat pain and inflammation in conditions such as rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis..

Sulindac sulfide was first approved for use in the United States in 1980 and is still in wide use today. It exists as an oral capsule, an oral suspension, and a topical gel. The most common side effects of sulindac sulfide are gastrointestinal, such as nausea, vomiting, and diarrhea. Less common side effects include headache, dizziness, and rash..

Sulindac sulfide works by inhibiting the synthesis of prostaglandins, which are compounds that play a role in pain and inflammation. It does this by blocking the enzyme cyclooxygenase (COX), which is responsible for the synthesis of prostaglandins..

There are two types of COX enzymes, COX-1 and COX-2. COX-1 is responsible for the synthesis of prostaglandins that are involved in the protection of the stomach lining. COX-2 is responsible for the synthesis of prostaglandins that are involved in pain and inflammation. Sulindac sulfide inhibits both COX-1 and COX-2..

While sulindac sulfide behaves reducing pain and inflammation, it can also cause gastrointestinal side effects. To reduce the risk of these side effects, sulindac sulfide is often taken with food..

Sulindac sulfide is a safe and effective medication for the treatment of pain and inflammation. However, like all medications, it has the potential for side effects. If you experience any side effects, talk to your doctor..

3D structure

Cartesian coordinates

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

2D drawing

 

Sulindac sulfide LFWHFZJPXXOYNR-MFOYZWKCSA-N chemical compound 2D structure molecule svg
Sulindac sulfide

 

Molecule descriptors

 
IUPAC name2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid
InChI codeInChI=1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
InChI KeyLFWHFZJPXXOYNR-MFOYZWKCSA-N
SMILESCSc1ccc(/C=C2/C(C)=C(CC(=O)O)c3cc(F)ccc32)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.

  • (Z)-2-(3-(4-(methylthio)benzylidene)-6-fluoro-2-methyl-3H-inden-1-yl)acetic acid
  • (Z)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetic acid
  • (Z)-5-Fluoro-2-methyl-1-((4-(methylthio)phenyl)methylene)-1H-indene-3-acetic acid
  • (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene) inden-3-ylacetic acid
  • (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetic acid
  • (Z)-5-fluoro-2-methyl-1-(4-methythiobenzylidene)-3-indenylacetic acid
  • (Z)-5-fluoro-2-methyl-1-[[4-(methylthio)-phenyl]methylene]-1H-indene-3-acetic acid
  • (Z)-Sulindac sulfide
  • 004S674
  • 1H-INDENE-3-ACETIC ACID, 5-FLUORO-2-METHYL-1-((4-(METHYLTHIO)PHENYL)METHYLENE)-, (1Z)-
  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylthio)phenyl)methylene)-, (Z)-
  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-[[4-(methylthio)phenyl]methylene]-
  • 1H-Indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylthio)phenyl]methylene]-, (1Z)-
  • 2-(3-(4-(methylthio)benzylidene)-6-fluoro-2-methyl-3H-inden-1-yl)acetic acid
  • 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid
  • 2-[(3z)-6-Fluoranyl-2-Methyl-3-[(4-Methylsulfanylphenyl)methylidene]inden-1-Yl]ethanoic Acid
  • 32004-67-4
  • 49627-27-2
  • 5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl acetic acid
  • 5-Fluoro-2-methyl-1-(p-methylthiobenzylidene)-3-indenyl acetic acid
  • 6UVA8S2DEY
  • AC-20512
  • BDBM50110164
  • CCG-208108
  • CS-0013817
  • DSSTox_CID_29004
  • DSSTox_GSID_49078
  • DSSTox_RID_83269
  • HY-B1786
  • NCGC00161601-01
  • NCGC00161601-02
  • NSC-747692
  • NSC747692
  • Q27145288
  • SFI
  • SR-01000944868
  • SR-01000944868-1
  • Sulindac Related Compound C
  • Sulindac Sulfide - CAS 32004-67-4
  • Sulindac Sulphane
  • Sulindac sulfide
  • Sulindac sulfide, (Z)-
  • Sulindac sulphide
  • Sulindac sulphide, (z)-
  • UNM-0000306137
  • Z-sulindac sulfide
  • [6-Fluoro-2-methyl-3-(4-methylsulfanyl-benzylidene)-3H-inden-1-yl]-acetic acid
  • cid_5352624
  • cis-Sulindac sulfide
  • {(1Z)-5-fluoro-2-methyl-1-[4-(methylsulfanyl)benzylidene]-1H-inden-3-yl}acetic acid
  • {6-Fluoro-2-methyl-3-[1-(4-methylsulfanyl-phenyl)-meth-(E)-ylidene]-3H-inden-1-yl}-acetic acid
  • {6-Fluoro-2-methyl-3-[1-[4-(methyl-lambda*4*-sulfanyl)-phenyl]-meth-(E)-ylidene]-3H-inden-1-yl}-acetic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC12404515
  • CAS-49627-27-2
  • UNII-6UVA8S2DEY
  • AKOS015965586
  • BRD-K76525302-001-01-3
  • DTXSID0049078
  • CHEMBL18797
  • CHEBI:75408
  • CHEBI:95256
  • Tox21_113636
  • Tox21_113636_1
  • EINECS 256-403-9
  • UPCMLD-DP020
  • UPCMLD-DP020:001
  • SCHEMBL2586650

Physico-Chemical properties

IUPAC name2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid
Molecular formulaC20H17FO2S
Molecular weight340.411
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.66
LogP5.4
Topological polar surface area62.6

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.