(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编号: 4477
• 分子式: C27H34F2O7
• 平均质量: 508.5514664
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: epitopic; difluprednate
• 商标名: Durezol
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 13.553358
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 3.004233
• LogD (pH = 7.4): 3.0042326
• Log P: 3.004233
• 摩尔折射率: 125.3756 cm^3
• 极化性: 48.93623 Å^3
• 极化表面积: 106.97 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 3.28
• LOG S: -4.72
• 溶解度: 9.70e-03 g/l

分子性质

安全信息

• RTECS编号: TU3831500
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.

参考文献

• 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)