2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 108
• Molecular Formular: C26H32F2O7
• Molecular Mass: 494.5248864
• Monoisotopic Mass: 494.2116098
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](OC(=O)C)([C@H](C3)C)C(=O)COC(=O)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: CC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F)C(=O)COC(=O)C
• InChI: InChI=1S/C26H32F2O7/c1-13-8-17-18-10-20(27)19-9-16(31)6-7-23(19,4)25(18,28)21(32)11-24(17,5)26(13,35-15(3)30)22(33)12-34-14(2)29/h6-7,9,13,17-18,20-21,32H,8,10-12H2,1-5H3/t13-,17-,18-,20-,21-,23-,24-,25-,26-/m0/s1
• InChIKey: BOBLHFUVNSFZPJ-JOYXJVLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: diflorasone
• Brand Name: Florone; Florone E; Maxiflor; Psorcon
• Synonyms: Diflorasone diacetate; Diflorasone Diacetate; Diflorasone; 6α,9-Difluoro-11β,17,21-trihydroxy-16 β-methyl-pregna-1,4-diene-3,20-dione 17,21-diacetate; DIFLORASONE DIACETATE; (6α,11β,16β)-17,21-Bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione; Dermaflor; Diacort; Diflorasone 17,21-Diacetate; Difulal; Florone; Maxiflor; Psorcon; Soriflor; 6α,9-二氟-11β,17,21-三羟基-16β-甲基孕甾-1,4-二烯-3,20-二酮 17,21-二乙酸酯; 双氟拉松乙酸酯

Database IDs

• CAS Number: 2557-49-5; 33564-31-7
• EC Number: 251-575-1
• MDL Number: MFCD00079159
• PubChem SID: 24894203; 160963571
• PubChem CID: 71414

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.553008
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.2241013
• LogD (pH = 7.4): 2.2241008
• Log P: 2.2241013
• Molar Refractivity: 120.6193 cm^3
• Polarizability: 47.113922 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.85
• LOG S: -4.63
• Solubility (Water): 1.16e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 222-224°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: TU3722000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H332-H351
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

MP Biomedicals - 02157696

(6α,9-Difluoro-11β,17,21-trihydroxy-
16β-methyl-pregna-1,4-diene-
3,20-dione 17,21-diacetate)

DrugBank - DB00223

• Drug Groups: approved
• Description: Diflorasone is a topical corticosteroid used to treat itching and inflammation of the skin.
• Indication: For relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.
• Pharmacology: 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.
• Toxicity: Topically applied diflorasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• Protein Binding: Bound to plasma proteins in varying degrees.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - D445500

An anti-inflammatory and anti-itching corticosteroid usually present in topical creams.

REFERENCES

• Dikunets, M., et al.: J. Anal. Chem., 64, 832 (2009)
• Maccaroni, E., et al.: Steroids, 74, 102 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)