基本情報
- CAS
426-13-1- 標準SMILES
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C- InChIKey
FAOZLTXFLGPHNG-KNAQIMQKSA-N- 分子式
- C22H29FO4
- 平均分子量
- 376.5 g/mol
- 単同位体質量
- 376.20498756
概要
Fluorometholone is a member of the class of glucocorticoids that is 1-progesterone substituted at positions 11beta and 17 by hydroxy groups, at position 6alpha by a methyl group and at position 9 by a fluoro group. Used for the treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe. It has a role as an anti-inflammatory drug. It is a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It is functionally related to a Delta(1)-progesterone.
名称と識別子
- 優先名称
- Fluorometholone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- 現地名
- フルオロメトロン
- 英語名
- Fluorometholone
- 分子式
- C22H29FO4
- 分子量
- 376.46
名称と別名
fluorometholone426-13-1OxyloneFluor-OpFML ForteFluorometolonaFluorometholonumFluorometoloneDTXSID70474359-Fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dioneFluaton(6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
名称をさらに表示
フルオロメトロンウルスノン9α-フルオロ-11β,17α-ジヒドロキシ-6α-メチルプレグナ-1,4-ジエン-3,20-ジオンフルコンフルアトンオキシロンフルオメソロンフルベースフルロンオドメール9-フルオロ-11β,17α-ジヒドロキシ-6α-メチル-1,4-プレグナジエン-3,20-ジオンレグレシンオロロンピトスフルメトロンコルチレットトリクリンフルオダームメソフロンフルオロメトロンTfluoromethaloneFlurometholoneFMLFlulon
物性
構造計算による物性
- XLogP
- 2
- 極性表面積
- 74.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 1
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 787
実験および物理化学的性質
Drugs
Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Pharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesMagnetic anisotropy
LogP
2
2.65
Solubility1.66e-02 g/L
Human Drugs
Breast Feeding; Lactation; Anti-Inflammatory Agents; Corticosteroids, Ophthalmic; Glucocorticoids;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
292-303
297 °C
Physical DescriptionSolid
Collision Cross Section
272.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID7047435]
182.45 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
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
Warning
H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (89.1%)
毒性情報
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- 3
- rtecs
- TU3834100
- 毒性
- rat,LD,oral,> 2gm/kg (2000mg/kg),Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2349, 1974.
- hs_code
- 29189900
- risk_code
- 20/21/22
- hazard_code
- Xn
- safety_code
- 36
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
S01BA07
S - Sensory organs
D - Dermatologicals
D - Dermatologicals
S - Sensory organs
C - Cardiovascular system
Pharmacodynamics
Corticosteroids such as fluorometholone inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation associated with inflammation.
Mechanism of Action
There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 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 A2. Their primary target is the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.
FDA Pharmacological Classification
SV0CSG527L
FLUOROMETHOLONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Fluorometholone is a Corticosteroid. The mechanism of action of fluorometholone is as a Corticosteroid Hormone Receptor Agonist.
FLUOROMETHOLONE
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
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.
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