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Fluocinolone Acetonide
Các tên gọi khác (38 ) :
  • 6alpha-Fluorotriamcinolone acetonide
  • 6alpha,9alpha-Difluoro-16alpha-hydroxyprednisolone 16,17-acetonide
  • Acetónida de fluocinolona
  • Acétonide de fluocinolone
  • Acetonido de fluocinolona
  • Coriphate
  • Cortiplastol
  • Derma-smoothe/fs
  • Dermalar
  • Flucinar
  • Flucort
  • Fluocet
  • Fluocinolon acetonid
  • Fluocinolonacetonid
  • Fluocinolone 16,17-acetonide
  • Fluocinoloni acetonidum
  • Fluonid
  • Fluotrex
  • Fluovitif
  • Flupollon
  • Fluzon
  • Iluvien
  • Jellin
  • Localyn
  • Omniderm
  • Percutina
  • Prodermin
  • Radiocin
  • Retisert
  • Sinalar
  • Synalar
  • Synamol
  • Synandone
  • Synandrone
  • Synemol
  • Synotic
  • Synsac
  • Tefunote
anti inflammatory agents, glucocorticoids
Thuốc Gốc
Small Molecule
CAS: 67-73-2
ATC: S02BA08, C05AA10, D07AC04, S01BA15
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C24H30F2O6
PTK: 452.4882
A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). It is also being investigated by Sivida and Alimera, under the brand name Medidur, as a sustained release intraocular implant for the treatment of diabetic macular edema.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C24H30F2O6
Phân tử khối
452.4882
Monoisotopic mass
452.201045102
InChI
InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
InChI Key
InChIKey=FEBLZLNTKCEFIT-VSXGLTOVSA-N
IUPAC Name
(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
Traditional IUPAC Name
fluocinolone acetonide
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
Độ tan chảy
266-268
Độ hòa tan
5.47e-02 g/l
logP
2.48
logS
-3.9
pKa (strongest acidic)
13.35
pKa (Strongest Basic)
-3.3
PSA
93.06 Å2
Refractivity
111.41 m3·mol-1
Polarizability
44.97 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
6
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Cơ Chế Tác Dụng : A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). It is also being investigated by Sivida and Alimera, under the brand name Medidur, as a sustained release intraocular implant for the treatment of diabetic macular edema. Fluocinolone Acetonide is a corticosteroid that binds to 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. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.
Dược Động Học :
▧ Absorption :
Rapidly absorbed (15 minutes)
▧ Metabolism :
Primarily hepatic, corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
▧ Route of Elimination :
Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
▧ Half Life :
1.3-1.7 hours
Chỉ Định : For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye (Retisert).
Liều Lượng & Cách Dùng : Cream - Topical
Implant - Intraocular
Liquid - Topical
Ointment - Topical
Shampoo - Topical
Solution - Topical
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Sản phẩm biệt dược : Derma-smoothe/FS
  • Công ty : Teva
    Sản phẩm biệt dược : Dermalar
  • Công ty :
    Sản phẩm biệt dược : DermOtic
  • Công ty : Jelfa
    Sản phẩm biệt dược : Flucinar
  • Công ty : Biolab
    Sản phẩm biệt dược : Fluonid
  • Công ty : Mayado Seiyaku
    Sản phẩm biệt dược : Flupollon
  • Công ty : Shinlon
    Sản phẩm biệt dược : Futocan
  • Công ty : Grünenthal
    Sản phẩm biệt dược : Jellin
  • Công ty : Recordati
    Sản phẩm biệt dược : Locafluo
  • Công ty : ICI
    Sản phẩm biệt dược : Mecloderm
  • Công ty : Bausch & Lomb
    Sản phẩm biệt dược : Retisert
  • Công ty : Astellas Pharma
    Sản phẩm biệt dược : Synalar
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00591
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6215
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506244
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01825
ChemSpider
http://www.chemspider.com/Chemical-Structure.5980.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0168-0064-15
PharmGKB
http://www.pharmgkb.org/drug/PA164754912
Wikipedia
http://en.wikipedia.org/wiki/Fluocinolone_acetonide
RxList
http://www.rxlist.com/cgi/generic4/retisert.htm
Drugs.com
http://www.drugs.com/cdi/fluocinolone-acetonide-implant.html
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