基本情報
- CAS
23674-86-4- 標準SMILES
CCCC(=O)O[C@]1(C(=O)COC(C)=O)CC[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@@]21C- InChIKey
WYQPLTPSGFELIB-JTQPXKBDSA-N- 分子式
- C27H34F2O7
- 平均分子量
- 508.5 g/mol
- 単同位体質量
- 508.22725987
概要
Difluprednate is a corticosteroid hormone and a butyrate ester.
名称と識別子
- 優先名称
- Difluprednate
- IUPAC
- [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
- 現地名
- ジフルプレドナート
- 英語名
- Difluprednate
- 分子式
- C27H34F2O7
- 分子量
- 508.55
名称と別名
difluprednate23674-86-4DurezolDFBADifluprednatoEpitopicDifluprednatumDTXSID0046773Difluoroprednisolone butyrate acetateS8A06QG2QEW 6309W-6309
名称をさらに表示
ジフルプレドネート21-アセチルオキシ-17α-ブチリルオキシ-6α,9α-ジフルオロ-11β-ヒドロキシプレグナ-1,4-ジエン-3,20-ジオンシフナールナルタール21-アセチルオキシ-6α,9-ジフルオロ-11β-ヒドロキシ-17-(1-オキソブトキシ)プレグナ-1,4-ジエン-3,20-ジオントリホモンマイザーサイベースジフルプレドナートエピトピックソロミーフルナートプラパスタ6Α,9Α-ジフルオロプレドニゾロン 21-アセタート 17-ブチラートジフルプレドナート (JAN)Difluprenatew6309myserDifluprednate-d5Difluprednate-d3
CM 9155[(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoateDTXCID80267736-alpha,9-alpha-Difluoroprednisolone 17-butyrate 21-acetate21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione (6alpha,11beta)-Pregna-1,4-diene-3,20-dione, 6-alpha,9-difluoro-11-beta,17,21-trihydroxy-, 21-acetate, 17-butyrate((6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta(a)phenanthren-17-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^(11,15))heptadeca-3,6-dien-14-yl butanoate
物性
構造計算による物性
- XLogP
- 3.4
- 極性表面積
- 107 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 9
- 回転可能結合数
- 8
- 重原子数
- 36
- 形式電荷
- 0
- 複雑度
- 1,050
実験および物理化学的性質
Drugs
Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Anti-Inflammatory Agents; Corticosteroids, Ophthalmic; Glucocorticoids;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point191-194
Physical DescriptionSolid
物理化学的性質
- 融点
- 191 · 191-194°
- 比旋光度
- 22 · D22 +31.7° (c = 0.5 in dioxane)
- 沸点
- 600.3 · 600.3±55.0 °C(Predicted)
- 比重(密度)
- 1.1869 · 1.1869 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- ジオキサン（微量）、メタノール（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 12.56 · 12.56±0.70(Predicted)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.
Danger
H302+H312+H332 (20%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, 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.
危険有害性情報
Hazard Classes and CategoriesRepr. 1B (20%)
毒性情報
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- 2
- rtecs
- TU3831500
- 毒性
- mouse,LD50,intraperitoneal,146mg/kg (146mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)BEHAVIORAL: FOOD INTAKE (ANIMAL),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 1066, 1984.
- hs_code
- 2937.29.9095
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
D - Dermatologicals
S - Sensory organs
QD - Dermatologicals
QS - Sensory organs
PharmacodynamicsDifluprednate is a corticosteroid used as an anti-inflammatory steroidal drug used primarily in ocular surgery.
Mechanism of Action
Corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins (lipocortins). It is postulated that these proteins control the biosynthesis of potent mediators of infammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Metabolism/Metabolites
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.
MeSH Pharmacological Classification
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
Absorption, Distribution and Excretion
Difluprednate penetrates the corneal epithelium rapidly and effectively. Low systemic absorption.
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.
Cellular LocationsCytoplasm
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関連反応
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化合物ノート
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