Tìm theo
Lumiracoxib
Các tên gọi khác (6 ) :
  • 2-((2-chloro-6-Fluorophenyl)amino)-5-methylbenzeneacetic acid
  • COX 189
  • COX-189
  • COX189
  • Lumiracoxibum
  • Prexige
cyclooxygenase 2 inhibitors
Thuốc Gốc
Small Molecule
CAS: 220991-20-8
ATC: M01AH06
CTHH: C15H13ClFNO2
PTK: 293.721
Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H13ClFNO2
Phân tử khối
293.721
Monoisotopic mass
293.061884577
InChI
InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)
InChI Key
InChIKey=KHPKQFYUPIUARC-UHFFFAOYSA-N
IUPAC Name
2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
Traditional IUPAC Name
lumiracoxib
SMILES
CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1
Độ hòa tan
5.49e-03 g/l
logP
3.9
logS
-4.7
pKa (strongest acidic)
4.11
pKa (Strongest Basic)
-1.9
PSA
49.33 Å2
Refractivity
75.91 m3·mol-1
Polarizability
28.53 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity.
Cơ Chế Tác Dụng : Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug. The mechanism of action of lumiracoxib is due to inhibition of prostaglandin synthesis via inhibition of cyclooygenase-2 (COX-2). Lumiracoxib does not inhibit COX-1 at therapeutic concentrations.
Dược Động Học :
▧ Absorption :
Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.
▧ Protein binding :
Highly bound to plasma proteins (>= 98%).
▧ Metabolism :
Hepatic oxidation and hydroxylation via CYP2C9. Three major metabolites have been identified in plasma: 4'-hydroxy-lumiracoxib, 5-carboxy-lumiracoxib, and 4'-hydroxy-5-carboxy-lumiracoxib.
▧ Half Life :
Terminal half-life is approximately 4 hours.
Độc Tính : Single oral doses in mice and rats resulted in mortality and/or moribundity at doses of 600 mg/kg and 500 mg/kg, respectively. Single intraperitoneal doses in mice and rats results in mortality/moribundity at 750 mg/kg and 1000 mg/kg, respectively. The maximum non-lethal single oral and intraperitoneal dose in mouse was 300 mg/kg and 250 mg/kg, respectively. In the rat it was 150 mg/kg and 250 mg/kg, respectively.
Chỉ Định : For the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.
Tương Tác Thuốc :
  • Acenocoumarol Lumiracoxib may increase the anticoagulant effect of acenocoumarol.
  • Anisindione Lumiracoxib may increase the anticoagulant effect of anisindione.
  • Dicoumarol Lumiracoxib may increase the anticoagulant effect of dicumarol.
  • Lithium The COX-2 inhibitor increases serum levels of lithium
  • Telmisartan Concomitant use of Telmisartan and Lumiracoxib may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
  • Timolol The NSAID, Lumiracoxib, may antagonize the antihypertensive effect of Timolol.
  • Tolbutamide Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Lumiracoxib. Consider alternate therapy or monitor for changes in Lumiracoxib therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
  • Trandolapril The NSAID, Lumiracoxib, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Lumiracoxib is initiated, discontinued or dose changed.
  • Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Lumiracoxib. Monitor for increased bleeding during concomitant thearpy.
  • Warfarin Lumiracoxib may increase the anticoagulant effect of warfarin.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty : Novartis
    Sản phẩm biệt dược : Prexige
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01283
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D03714
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50207446
PharmGKB
http://www.pharmgkb.org/drug/PA164769031
Wikipedia
http://en.wikipedia.org/wiki/Lumiracoxib
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