Flurandrenolide

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

What is the Flurandrenolide?

The molecule Flurandrenolide presents a molecular formula of C24H33FO6 and its IUPAC name is (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one.

Flurandrenolide is a synthetic corticosteroid with anti-inflammatory and antipruritic properties. It is used topically as a cream, ointment, or lotion for the treatment of various skin disorders such as eczema, psoriasis, and contact dermatitis. Flurandrenolide is also used topically as a tape or patch for the treatment of plaque psoriasis..

3D structure

Cartesian coordinates

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

2D drawing

 

Flurandrenolide POPFMWWJOGLOIF-XWCQMRHXSA-N chemical compound 2D structure molecule svg
Flurandrenolide

 

Molecule descriptors

 
IUPAC name(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
InChI codeInChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
InChI KeyPOPFMWWJOGLOIF-XWCQMRHXSA-N
SMILESCC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1

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.

  • (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
  • (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-17-en-16-one
  • (2S,6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-2-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a,10,10-tetramethyl-5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4(2H)-one
  • (4R,8S,9S,11S,13R,19S)-19-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
  • (6?,11?,16?)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregn-4-ene-3,20-dione
  • 1524-88-5
  • 524F885
  • 6.alpha.-Fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregn-4-ene-3,20-dione, cyclic 16,17-acetal with acetone
  • 6alpha-Fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione, cyclic 16,17-acetal with acetone
  • 6alpha-Fluoro-11beta,16alpha,17,21-tetrahydroxyprogesterone cyclic 16,17-acetal with acetone
  • 6alpha-Fluoro-16alpha-hydroxyhydrocortisone 16,17-acetonide
  • 8EUL29XUQT
  • Acetonide of 6alpha-fluoro-16alpha-hydroxyhydrocortisone
  • Alondra-F
  • BPBio1_000715
  • BSPBio_000649
  • CCG-220645
  • CORDRAN SP
  • CORDRAN-N COMPONENT FLURANDRENOLIDE
  • CS-4526
  • Cordran
  • D00328
  • DB00846
  • DSSTox_CID_27434
  • DSSTox_GSID_47434
  • DSSTox_RID_82344
  • Drenison
  • Drocort
  • FLURANDRENOLIDE COMPONENT OF CORDRAN-N
  • Floudroxycortide
  • Fludrossicortide
  • Fludroxicortida
  • Fludroxicortide
  • Fludroxicortidum
  • Fludroxycortid
  • Fludroxycortide
  • Fludroxycortide (JAN/INN)
  • Fludroxycortidum
  • Fluorandrenolone
  • Fluorandrenolone acetonide
  • Flurandrenolide
  • Flurandrenolone
  • Flurandrenolone acetonide
  • GTPL7606
  • HMS1570A11
  • HMS2097A11
  • HMS2233C04
  • HMS3714A11
  • HSDB 3084
  • HY-B1013
  • Haelan
  • Haldrone-F
  • L 33379
  • MLS000069556
  • MLS001148136
  • NCGC00016586-01
  • NCGC00023234-03
  • NCGC00023234-05
  • NCGC00256709-01
  • NSC 757869
  • NSC-757869
  • Opera_ID_1618
  • PREGN-4-ENE-3,20-DIONE, 6-FLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, (6.ALPHA.,11.BETA.,16.ALPHA.)-
  • Pregn-4-ene-3,20-dione, 6-alpha-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
  • Pregn-4-ene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-
  • Pregn-4-ene-3,20-dione, 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
  • Prestwick0_000645
  • Prestwick1_000645
  • Prestwick2_000645
  • Prestwick3_000645
  • Prestwick_1065
  • Q5462632
  • SMR000058825
  • SR-01000003119
  • SR-01000003119-3
  • Sermaka
  • W-108052
  • flurandrenolide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097308
  • CAS-1524-88-5
  • UNII-8EUL29XUQT
  • BRD-K00824317-001-03-0
  • DTXSID2047434
  • CHEMBL1201012
  • CHEBI:5127
  • Tox21_110509
  • Tox21_302611
  • Tox21_110509_1
  • EINECS 216-196-8
  • SPBio_002570
  • SCHEMBL4694

Physico-Chemical properties

IUPAC name(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
Molecular formulaC24H33FO6
Molecular weight436.514
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity110.94
LogP2.5
Topological polar surface area93.1

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.