Diflorasone
Basic information
- CAS
2557-49-5- Standard SMILES
C[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- InChIKey
WXURHACBFYSXBI-XHIJKXOTSA-N- Molecular formula
- C22H28F2O5
- Average molar mass
- 410.5 g/mol
- Monoisotopic mass
- 410.19048031
Overview
Diflorasone is the 16beta-analogue of flumethasone. It is used as the 17,21-diacetate as a topical anti-inflammatory and antipruritic in the treatment of various skin disorders. It has a role as an anti-inflammatory drug. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Diflorasone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,16S,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
- English name
- Diflorasone
- Molecular formula
- C22H28F2O5
- Molecular weight
- 410.46
Names & synonyms
diflorasone2557-49-5DiflorasonaDiflorasonumMurodeT2DHJ9645W6alpha,9-Difluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dioneCHEBI:59750DTXSID201036185(6alpha,11beta,16beta)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-dien-5-one(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
Show more names
DifloasoneDiflorasone [INN:BAN]Diflorasone USP/EP/BPDiflorasone, 10 mM in DMSOFluticasone Propionate Impurity 28Fluticasone propionate impurity 37、 Diflorasone11β,17α,21-trihydroxy-6α,9α-difluoro-16β-methylpregna-1,4-diene-3,20-dione(6α,11β,16β)-6,9-Difluoro-11,17,21-trihydroxy-16-Methyl-pregna-1,4-diene-3,20-dione
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 839
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.1
Solubility8.53e-02 g/L
Human DrugsBreast Feeding; Lactation; Corticosteroids, Topical; Glucocorticoids; Anti-Inflammatory Agents
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 228 · 228-239°C
- Boiling point
- 569.8 · 569.8±50.0 °C(Predicted)
- Density
- 1.36 · 1.36±0.1 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- Methanol (Slightly)
- pka
- 11.98 · 11.98±0.70(Predicted)
- form
- Solid
- color
- Off-White to Pale Yellow
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H312 (60%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P203, P260, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P308+P316, P317, P318, P321, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (60%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS08,GHS07
- Hazard statements
- H312-H361
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501-P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
QD - Dermatologicals
Protein BindingBound to plasma proteins in varying degrees.
Pharmacodynamics
Like other topical corticosteroids, diflorasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Diflorasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
Mechanism of Action
The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A<sub>2</sub> inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A<sub>2</sub>.
Metabolism/MetabolitesMetabolized, primarily in the liver, and then excreted by the kidneys.
FDA Pharmacological Classification
T2DHJ9645W
DIFLORASONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Diflorasone is a Corticosteroid. The mechanism of action of diflorasone is as a Corticosteroid Hormone Receptor Agonist.
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
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