Tìm theo
Etretinate
Thuốc Gốc
Small Molecule
CAS: 54350-48-0
ATC: D05BB01
CTHH: C23H30O3
PTK: 354.4825
Etretinate is a medication used to treat severe psoriasis. It is a synthetic aromatic retinoid. The mechanism of action of etretinate is still incompletely understood although, like retinoic acid, it is thought to interfere with the terminal differentiation of keratinocytes. It is thought to bind to the retinoic acid receptors. Etretinate is also believed to enhance the binding of cAMP to the regulatory RI subunit of cAMP dependent protein kinases. It was removed from the United States market in 1998 and the Canadian market in 1996 as a psoriasis medication, due to the high risk of birth defects. Etretinate is now used to treat T-cell lymphomas. It also appears to inhibit NADH oxidase activity.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C23H30O3
Phân tử khối
354.4825
Monoisotopic mass
354.219494826
InChI
InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
InChI Key
InChIKey=HQMNCQVAMBCHCO-DJRRULDNSA-N
IUPAC Name
ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
Traditional IUPAC Name
ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
SMILES
CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C)C(C)=C(OC)C=C1C
Độ tan chảy
104-105
Độ hòa tan
4.05e-04 g/l
logP
6.5
logS
-5.9
pKa (Strongest Basic)
-4.8
PSA
35.53 Å2
Refractivity
113.68 m3·mol-1
Polarizability
42.98 Å3
Rotatable Bond Count
8
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Dược Lực Học : The active metabolite responsible for etretinate's effects, acitretin, is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.
Cơ Chế Tác Dụng : Etretinate is a medication used to treat severe psoriasis. It is a synthetic aromatic retinoid. The mechanism of action of etretinate is still incompletely understood although, like retinoic acid, it is thought to interfere with the terminal differentiation of keratinocytes. It is thought to bind to the retinoic acid receptors. Etretinate is also believed to enhance the binding of cAMP to the regulatory RI subunit of cAMP dependent protein kinases. It was removed from the United States market in 1998 and the Canadian market in 1996 as a psoriasis medication, due to the high risk of birth defects. Etretinate is now used to treat T-cell lymphomas. It also appears to inhibit NADH oxidase activity. The mechanism of action of the active metabolite, acitretin, is unknown, however it is believed to work by targeting specific receptors (retinoid receptors) in the skin which help normalize the growth cycle of skin cells.
Dược Động Học :
▧ Absorption :
Absorbed in the small intestine. Studies in normal volunteers indicate that the absorption of etretinate is greater in patients consuming whole milk or a high-fat diet than in patients in a fasting state.
▧ Protein binding :
More than 99% bound to plasma proteins, predominantly lipoproteins, whereas its active metabolite, acetretin (etretin), is predominantly bound to albumin.
▧ Metabolism :
Extensively metabolized, with significant first-pass metabolism to the pharmacologically active acid form. Subsequent metabolism results in the inactive 13-cis acid form, chain-shortened breakdown products, and conjugates that are ultimately excreted.
▧ Half Life :
In one study, the apparent terminal half-life of etretinate after 6 months of therapy was approximately 120 days. In another study of 47 patients who had undergone chronic therapy with etretinate, 5 patients had detectable serum drug concentrations (0.5 to 12 ng/mL) 2.1 to 2.9 years after therapy was completed.
Độc Tính : Symptoms of overdose include headache and vertigo.
Chỉ Định : For the treatment of severe psoriasis in adults.
Tương Tác Thuốc :
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Tegison
  • Sản phẩm biệt dược : Tigason
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00926
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5282375
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504486
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00316
ChemSpider
http://www.chemspider.com/Chemical-Structure.3196.html
PharmGKB
http://www.pharmgkb.org/drug/PA449554
Wikipedia
http://en.wikipedia.org/wiki/Etretinate
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