Tìm theo
Celecoxib
Các tên gọi khác (5 ) :
  • Celebrex
  • Celecoxib
  • Célécoxib
  • Celecoxibum
  • P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide
Thuốc giảm đau, hạ sốt, chống viêm không steroid, điều trị Gút và các bệnh xương khớp
Thuốc Gốc
Small Molecule
CAS: 169590-42-5
ATC: L01XX33, M01AH01
ĐG : 4uOrtho LLC , http://www.4udr.com
CTHH: C17H14F3N3O2S
PTK: 381.372
Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra. Celecoxib is available by prescription in capsule form.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H14F3N3O2S
Phân tử khối
381.372
Monoisotopic mass
381.075882012
InChI
InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChI Key
InChIKey=RZEKVGVHFLEQIL-UHFFFAOYSA-N
IUPAC Name
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional IUPAC Name
celecoxib
SMILES
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
Độ tan chảy
158 °C
Độ hòa tan
Very low water solubility (3.3 mg/L)
logP
3.9
logS
-4.9
pKa (strongest acidic)
10.7
pKa (Strongest Basic)
-0.42
PSA
77.98 Å2
Refractivity
92.23 m3·mol-1
Polarizability
35.2 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Celecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Celecoxib is used to treat rheumatoid arthritis, osteoarthritis, and familial adenomatous polyposis (FAP). Because of its lack of platelet effects, celecoxib is not a substitute for aspirin for cardiovascular prophylaxis. It is not known if there are any effects of celecoxib on platelets that may contribute to the increased risk of serious cardiovascular thrombotic adverse events associated with the use of celecoxib. Inhibition of PGE2 synthesis may lead to sodium and water retention through increased fluid reabsorption in the renal medullary thick ascending loop of Henle and perhaps other segments of the distal nephron. In the collecting ducts, PGE2 appears to inhibit water reabsorption by counteracting the action of antidiuretic hormone.
Cơ Chế Tác Dụng : Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra. Celecoxib is available by prescription in capsule form. The mechanism of action of celecoxib is believed to be due to inhibition of prostaglandin synthesis. Unlike most NSAIDs, which inhibit both types of cyclooxygenases (COX-1 and COX-2), celecoxib is a selective noncompetitive inhibitor of cyclooxygenase-2 (COX-2) enzyme. It binds with its polar sulfonamide side chain to a hydrophilic side pocket region close to the active COX-2 binding site. Both COX-1 and COX-2 catalyze the conversion of arachidonic acid to prostaglandin (PG) H2, the precursor of PGs and thromboxane.
Dược Động Học :
▧ Absorption :
Well absorbed in the gastrointestinal tract. When a single dose of 200 mg is given to healthy subjects, peak plasma levels occur 3 hours after an oral dose. The peak plasma level is 705 ng/mL. Absolute bioavailability studies have not been conducted. When multiple doses are given, steady-state is reached on or before Day 5. When taken with a high fat meal, peak plasma levels are delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20%.
▧ Volume of Distribution :
Apparent volume of distribution at steady state (Vdss/F), 200 mg single dose, healthy subjects = 429 L
▧ Protein binding :
97%, primarily to albumin and, to a lesser extent, a1-acid glycoprotein. Celecoxib is not preferentially bound to red blood cells.
▧ Metabolism :
Hepatic. Celecoxib metabolism is primarily mediated via cytochrome P450 2C9. Three metabolites, a primary alcohol, the corresponding carboxylic acid and its glucuronide conjugate, have been identified in human plasma. CYP3A4 is also involved in the hydroxylation of celecoxib but to a lesser extent. These metabolites are inactive as COX-1 or COX-2 inhibitors.
▧ Route of Elimination :
Celecoxib is eliminated predominantly by hepatic metabolism with little (<3%) unchanged drug recovered in the urine and feces. 57% of the oral dose is excreted in the feces and 27% is excreted into the urine. The primary metabolite in urine and feces was the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is low.
▧ Half Life :
The effective half-life is approximately 11 hours when a single 200 mg dose is given to healthy subjects. Terminal half-life is generally variable because of the low solubility of the drug thus prolonging absorption.
▧ Clearance :
Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr.
Độc Tính : Symptoms of overdose include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.
Chỉ Định : For relief and management of osteoarthritis (OA), rheumatoid arthritis (RA), juvenile rheumatoid arthritis (JRA), ankylosing spondylitis, acute pain, primary dysmenorrhea and oral adjunct to usual care for patients with familial adenomatous polyposis
Tương Tác Thuốc :
  • Acenocoumarol Celecoxib may increase the anticoagulant effect of acenocoumarol.
  • Anisindione Celecoxib may increase the anticoagulant effect of anisindione.
  • Azilsartan medoxomil Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
  • Colesevelam Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
  • Dicoumarol Celecoxib may increase the anticoagulant effect of dicumarol.
  • Eltrombopag Eltrombopag increases levels of Celecoxib via metabolism decrease.
  • Fluconazole Fluconazole may increase the effect of celecoxib.
  • Lithium The COX-2 inhibitor increases serum levels of lithium
  • Pralatrexate NSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
  • Rifampicin Rifampin, a strong CYP2C9 inducer, may decrease the serum levels of celecoxib by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects if rifampin is initiated, discontinued or dose changed.
  • Telmisartan Concomitant use of Telmisartan and Celecoxib may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
  • Timolol The NSAID, Celecoxib, may antagonize the antihypertensive effect of Timolol.
  • Tolbutamide Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Celecoxib. Consider alternate therapy or monitor for changes in Celecobix therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
  • Trandolapril The NSAID, Celecoxib, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Celecoxib is initiated, discontinued or dose changed.
  • Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Celecoxib. Monitor for increased bleeding during concomitant thearpy.
  • Tretinoin The moderate CYP2C8 inhibitor, Celecoxib, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Celecoxib is initiated, discontinued to dose changed.
  • Vilazodone Selective Serotonin Reuptake Inhibitors may enhance the antiplatelet effect of NSAID (COX-2 Inhibitor). To minimize the risk of bleeding associated with this combination, consider using alternative analgesics, when appropriate, and/or addition of an gastroprotective agent, such as a proton pump inhibitor for the time that combined selective serotonin reuptake inhibitor (SSRIs) and nonsteroidal anti-inflammatory drugs (NSAIDs) is necessary.
  • Warfarin Celecoxib may increase the anticoagulant effect of warfarin.
Liều Lượng & Cách Dùng : Capsule - Oral - 50 mg, 100 mg, 200 mg, 400 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Keyfarm
    Sản phẩm biệt dược : Articox
  • Công ty : Nabiqasim
    Sản phẩm biệt dược : Articoxib
  • Công ty : Standpharm
    Sản phẩm biệt dược : Artiflex
  • Công ty : Pfizer
    Sản phẩm biệt dược : Artilog
  • Công ty : Pharmalab
    Sản phẩm biệt dược : Artix
  • Công ty : Intipharma
    Sản phẩm biệt dược : Artrixib
  • Công ty : Infarmasa
    Sản phẩm biệt dược : Blockten
  • Công ty : Farmindustria
    Sản phẩm biệt dược : Caditar
  • Công ty : Farmacoop
    Sản phẩm biệt dược : Cefinix
  • Công ty : Sun
    Sản phẩm biệt dược : Celact
  • Công ty : Pfizer
    Sản phẩm biệt dược : Celebra
  • Công ty : Pfizer
    Sản phẩm biệt dược : Celebrex
  • Công ty : Pfizer
    Sản phẩm biệt dược : Onsenal
  • Công ty : Pfizer
    Sản phẩm biệt dược : Valdyne
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00482
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2662
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505596
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07589
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00567
ChemSpider
http://www.chemspider.com/Chemical-Structure.2562.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=11639
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0025-1515-01
PharmGKB
http://www.pharmgkb.org/drug/PA448871
Wikipedia
http://en.wikipedia.org/wiki/Celecoxib
RxList
http://www.rxlist.com/cgi/generic/coxib.htm
Drugs.com
http://www.drugs.com/celecoxib.html
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