Fluticasone

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

What is the Fluticasone?

The molecule Fluticasone presents a molecular formula of C22H27F3O4S and its IUPAC name is S-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate.

Fluticasone (FLU-tik-a-sone) is a man-made steroid that is used to treat nasal and lung problems. These problems include seasonal or year-round allergies, asthma, bronchitis, and emphysema. Fluticasone is a white powder with a molecular weight of 507.6 and the following chemical structure:.

Fluticasone belongs to a class of drugs called corticosteroids. Corticosteroids are hormones that are produced naturally by the adrenal gland. They have many important functions, including control of inflammatory reactions..

Fluticasone is used to treat the symptoms of allergies, asthma, and bronchitis. It works by preventing the release of substances in the body that cause inflammation..

Fluticasone exists as a nasal spray and an inhalation powder. It can be found as a cream, ointment, and lotion..

Fluticasone is usually used once or twice a day. The nasal spray is usually used once or twice a day. The inhalation powder is usually used two or three times a day. The cream, ointment, and lotion are usually applied once or twice a day..

Fluticasone may cause side effects. Tell your doctor if any of these symptoms are severe or do not go away:.

headache.

nausea.

vomiting.

diarrhea.

stomach pain.

dizziness.

trouble sleeping.

dry mouth.

nosebleed.

sore throat.

cough.

hoarseness.

runny nose.

increased appetite.

weight gain.

muscle weakness.

tremor.

anxiety.

nervousness.

irritability.

If you experience any of the following symptoms, call your doctor immediately:.

vision problems.

eye pain.

ear pain.

flu-like symptoms.

rash.

hives.

itching.

difficulty breathing or swallowing.

wheezing.

swelling of the face, throat, tongue, lips, eyes, hands, feet, ankles, or lower legs.

dizziness.

lightheadedness.

fainting.

Fluticasone may cause other side effects. Call your doctor if you have any unusual problems while you are taking this medication..

If you experience a serious side effect, you or your doctor may send a report to the Food and Drug Administration's (FDA) MedWatch Adverse Event Reporting program online (http://www.fda.gov/Safety/MedWatch) or by phone (1-800-332-1088)..

3D structure

Cartesian coordinates

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

2D drawing

 

Fluticasone MGNNYOODZCAHBA-GQKYHHCASA-N chemical compound 2D structure molecule svg
Fluticasone

 

Molecule descriptors

 
IUPAC nameS-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
InChI codeInChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
InChI KeyMGNNYOODZCAHBA-GQKYHHCASA-N
SMILESC[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)SCF

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.

  • 566F533
  • 90566-53-3
  • AC-456
  • Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, S-(fluoromethyl) ester, (6alpha,11beta,16alpha,17alpha)-
  • BIDD:GT0819
  • C07815
  • CS-0009547
  • CUT2W21N7U
  • D07981
  • DB13867
  • EX-A4418
  • Fluticasona
  • Fluticasone
  • Fluticasone (INN)
  • Fluticasone, Inhaled
  • Fluticasone, topical
  • Fluticasonum
  • GTPL6699
  • HSDB 7740
  • HY-B0603
  • Q1002165
  • S-(FLUOROMETHYL) (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-11,17-DIHYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIENE-17-CARBOTHIOATE
  • S-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
  • S-(fluoromethyl) (6alpha,11beta,16alpha,17alpha)-6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioate
  • fluticasone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097438
  • UNII-CUT2W21N7U
  • DTXSID0044022
  • CHEMBL1201396
  • CHEBI:5134
  • SCHEMBL4069

Physico-Chemical properties

IUPAC nameS-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
Molecular formulaC22H27F3O4S
Molecular weight444.508
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity108.49
LogP3.5
Topological polar surface area99.9

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.