Difluprednate

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

What is the Difluprednate?

The molecule Difluprednate presents a molecular formula of C27H34F2O7 and its IUPAC name is [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate.

Difluprednate is a molecule that belongs to the class of corticosteroids. It is used as an anti-inflammatory and immunosuppressive drug. It is structurally similar to prednisolone and has similar effects on the body. Difluprednate is used to treat inflammatory conditions such as rheumatoid arthritis, lupus, and psoriasis. It is also used to treat immune-mediated diseases such as Crohn's disease and ulcerative colitis. Difluprednate is a potent drug and should be used with caution in patients with a history of cardiovascular disease, hypertension, or diabetes..

3D structure

Cartesian coordinates

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

2D drawing

 

Difluprednate WYQPLTPSGFELIB-JTQPXKBDSA-N chemical compound 2D structure molecule svg
Difluprednate

 

Molecule descriptors

 
IUPAC name[(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
InChI codeInChI=1S/C27H34F2O7/c1-5-6-23(34)36-26(22(33)14-35-15(2)30)10-8-17-18-12-20(28)19-11-16(31)7-9-24(19,3)27(18,29)21(32)13-25(17,26)4/h7,9,11,17-18,20-21,32H,5-6,8,10,12-14H2,1-4H3/t17-,18-,20-,21-,24-,25-,26-,27-/m0/s1
InChI KeyWYQPLTPSGFELIB-JTQPXKBDSA-N
SMILESCCCC(=O)O[C@]1(C(=O)COC(C)=O)CC[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@@]21C

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,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl butanoate
  • (6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetoxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl butyrate
  • (6alpha,11beta)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dion
  • 21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione (6alpha,11beta)-
  • 23674-86-4
  • 6-alpha,9-alpha-Difluoroprednisolone 17-butyrate 21-acetate
  • 6.ALPHA.,9-DIFLUORO-11.BETA.,17,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE 21-ACETATE 17-BUTYRATE
  • 674D864
  • 6ALPHA,9ALPHA-DIFLUOROPREDNISOLONE 21-ACETATE 17-BUTYRATE
  • 6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate
  • 6alpha-9-Difluoroprednisolone 21-acetate 17-butyrate
  • A932746
  • AB00383058_10
  • ACT03289
  • AS-15800
  • CCG-269762
  • CM 9155
  • D01266
  • D5579
  • DB06781
  • DFBA
  • DSSTox_CID_26773
  • DSSTox_GSID_46773
  • DSSTox_RID_81894
  • Difluoroprednisolone butyrate acetate
  • Difluprednate
  • Difluprednate (JAN/USAN/INN)
  • Difluprednato
  • Difluprednatum
  • Durezol
  • Epitopic
  • GTPL7474
  • HMS2231D18
  • HY-17569
  • MFCD00214273
  • MLS000028663
  • MLS001148580
  • MLS001333701
  • Myser
  • NCGC00168749-01
  • Opera_ID_1287
  • Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6.alpha.,11.beta.)-
  • Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6alpha,11beta)-
  • Pregna-1,4-diene-3,20-dione, 6-alpha,9-difluoro-11-beta,17,21-trihydroxy-, 21-acetate, 17-butyrate
  • Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6a,11b)-
  • Q-101389
  • Q736113
  • S8A06QG2QE
  • SMR000058924
  • SR-01000000265
  • SR-01000000265-4
  • W 6309
  • W-6309
  • [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
  • difluprednate
  • s4095
  • st60-1

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4212945
  • CAS-23674-86-4
  • UNII-S8A06QG2QE
  • DTXSID0046773
  • CHEMBL1201749
  • CHEBI:31485
  • Tox21_112628
  • EINECS 245-815-4
  • SCHEMBL4580

Physico-Chemical properties

IUPAC name[(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
Molecular formulaC27H34F2O7
Molecular weight508.551
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity126.29
LogP3.5
Topological polar surface area107.0

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.