(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

• ChemBase ID: 4477
• Molecular Formular: C27H34F2O7
• Molecular Mass: 508.5514664
• Monoisotopic Mass: 508.22725987
• SMILES: CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F)O)C)C(=O)COC(=O)C
• Canonical SMILES: CCCC(=O)O[C@@]1(CC[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/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
• InChIKey: WYQPLTPSGFELIB-JTQPXKBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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; (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,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl butanoate
• IUPAC Traditional name: epitopic; difluprednate
• Brand Name: Durezol
• Synonyms: Difluoroprednisolone butyrate acetate; DFBA; Difluprednate; Difluprednate; 6α,9α-Difluoroprednisolone 21-acetate 17-butyrate; (6α,11β)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-pregna-1,4-diene-3,20-dione; 6a,9-Difluoro-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-Acetate 17-Butyrate; 6α,9-Difluoroprednisolone 21-Acetate 17-Butyrate; Epitopic; Myser; W 6309

Database IDs

• CAS Number: 23674-86-4
• EC Number: 245-815-4
• MDL Number: MFCD00214273
• PubChem SID: 99443292; 24894018; 160967909
• PubChem CID: 443936

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.553358
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.004233
• LogD (pH = 7.4): 3.0042326
• Log P: 3.004233
• Molar Refractivity: 125.3756 cm^3
• Polarizability: 48.93623 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.28
• LOG S: -4.72
• Solubility (Water): 9.70e-03 g/l

PROPERTIES

Safety Information

• RTECS: TU3831500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C27H34F2O7

DETAILS

DrugBank - DB06781

• Drug Groups: approved
• Description: Difluprednate is a topical corticosteroid indicated for the treatment of infammation and pain associated with ocular surgery. It was approved by the the US Food and Drug Administration (FDA) on June 24, 2008.
• Indication: For the treatment of inflammation and pain associated with ocular surgery.
• Pharmacology: Difluprednate is a corticosteroid used as an anti-inflammatory steroidal drug used primarily in ocular surgery.
• Toxicity: Preclinical pharmacokinetic and toxicity studies have established that difluprednate ophthalmic emulsion 0.05% given 4 times a day is not toxic to the eye.
• Biotransformation: Difluprednate is rapidly deacetylated in the aqueous humor to difluoroprednisolone butyrate (DFB), the drug’s active metabolite. Endogenous tissue esterases then metabolize DFB to the inert metabolite hydroxyfluoroprednisolone butyrate (HFB), which limits systemic exposure to the active compound.
• Absorption: Difluprednate penetrates the corneal epithelium rapidly and effectively. The systemic absorption of difuprednate after ocular instillation of difluprednate is limited.
• Elimination: 78.5% of radioactivity was excreted aftert 24 hours, and 99.5% by 7 days after a single dose of labeled difluprednate instilled in the right eyes of pigmented rabbits.
• References: Korenfeld MS, Silverstein SM, Cooke DL, Vogel R, Crockett RS: Difluprednate ophthalmic emulsion 0.05% for postoperative inflammation and pain. J Cataract Refract Surg. 2009 Jan;35(1):26-34. [Pubmed] ; Jamal KN, Callanan DG: The role of difluprednate ophthalmic emulsion in clinical practice. Clin Ophthalmol. 2009;3:381-90. Epub 2009 Jun 29. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - D445925

A corticosteroid (derivative of prednisolone), approved for the treatment of post-operative ocular inflammation.

REFERENCES

• Korenfeld MS, Silverstein SM, Cooke DL, Vogel R, Crockett RS: Difluprednate ophthalmic emulsion 0.05% for postoperative inflammation and pain. J Cataract Refract Surg. 2009 Jan;35(1):26-34. Pubmed
• Jamal KN, Callanan DG: The role of difluprednate ophthalmic emulsion in clinical practice. Clin Ophthalmol. 2009;3:381-90. Epub 2009 Jun 29. Pubmed
• Kapp, A., et al.: J. Allergy and Clin. Immunol., 110, 277 (2002)
• Yasueda, S., et al.: J. Pharm. Biomed. Anal., 30, 1735 (2002)
• Yamaguchi, M., et al.: Int. J. Pharm., 301, 121 (2002)