Flumethasone

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

What is the Flumethasone?

The molecule Flumethasone presents a molecular formula of C22H28F2O5 and its IUPAC name is (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one.

Flumethasone is a synthetic glucocorticoid or corticosteroid drug. It is a white to creamy-white, odorless, crystalline powder. It is insoluble in water, slightly soluble in alcohol, and freely soluble in chloroform and in acetone..

The chemical name for flumethasone is 9-fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione. Its molecular weight is 392.47..

Flumethasone is indicated for the treatment of inflammatory and allergic disorders. These include eczema, psoriasis, contact dermatitis, atopic dermatitis, drug eruptions, seborrheic dermatitis, anogenital pruritus, asthma, bronchitis, and COPD..

Flumethasone may also be used for other conditions as determined by your doctor..

3D structure

Cartesian coordinates

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

2D drawing

 

Flumethasone WXURHACBFYSXBI-GQKYHHCASA-N chemical compound 2D structure molecule svg
Flumethasone

 

Molecule descriptors

 
IUPAC name(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
InChI KeyWXURHACBFYSXBI-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)CO

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.

  • (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-5-one
  • (6?,11?,16?)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
  • (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  • (6S,9R,10S,11S,13S,16R,17R)-6,9-Difluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
  • 135F173
  • 2135-17-3
  • 6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • 6-alpha-Fluorodexamethasone
  • 6.alpha., 9-Difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1, 4-diene-3,20-dione
  • 6.alpha., 9.alpha.-Difluoro-16.alpha.-methylprednisolone
  • 6.alpha.,9-Difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione
  • 6.alpha.-Fluorodexamethasone
  • 6alpha,9-Difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione
  • 6alpha,9-Difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione (Flumetasone)
  • 6alpha,9alpha-Difluoro-16alpha-methylprednisolone
  • 6alpha-Fluoro-dexamethasone
  • 6alpha-Fluorodexamethasone
  • A855571
  • AC-2069
  • AMY38487
  • AS-12534
  • Anaprime
  • Aniprime
  • BPBio1_000758
  • BRN 5645455
  • BSPBio_000688
  • CCG-220734
  • CS-4573
  • Cortexilar
  • D04208
  • DB00663
  • DSSTox_CID_25365
  • DSSTox_GSID_45365
  • DSSTox_RID_80828
  • EC 218-370-9
  • F0945
  • Flucort (Veterinary)
  • Flucorticin
  • Flumetasona
  • Flumetasone
  • Flumetasone (INN)
  • Flumetasonum
  • Flumethason
  • Flumethasone
  • Flumethasone (USAN)
  • Flumethasonum
  • Fluvet
  • HMS1570C10
  • HMS2097C10
  • HMS2234B11
  • HMS3714C10
  • HY-B1051
  • LR3CD8SX89
  • MFCD00056464
  • MLS000028618
  • MLS001077306
  • Methagon
  • NCGC00016604-01
  • NCGC00021761-03
  • NCGC00021761-05
  • NCGC00021761-06
  • NSC 54702
  • NSC-54702
  • NSC54702
  • Opera_ID_1501
  • Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17, 21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-
  • Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-
  • Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-
  • Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6a,11b,16a)-
  • Prestwick0_000734
  • Prestwick1_000734
  • Prestwick2_000734
  • Prestwick3_000734
  • Prestwick_229
  • Q-101387
  • Q4383636
  • RS 2177
  • RS-2177
  • SMP1_000127
  • SMR000058690
  • SR-01000003144
  • SR-01000003144-3
  • T72075
  • U-10,974
  • U-10974
  • flumethasone
  • s4088

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3983936
  • CAS-2135-17-3
  • UNII-LR3CD8SX89
  • AKOS005256462
  • AKOS015895435
  • BRD-K61496577-001-03-8
  • BRD-K61496577-001-20-2
  • DTXSID2045365
  • CHEMBL1201392
  • CHEBI:34764
  • Tox21_110518
  • Tox21_110518_1
  • EINECS 218-370-9
  • SPBio_002627
  • SCHEMBL4046

Physico-Chemical properties

IUPAC name(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC22H28F2O5
Molecular weight410.452
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity102.01
LogP1.8
Topological polar surface area94.8

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.