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Namespace Prefixes

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Statements

Subject Item
n2:DB00482
rdf:type
n3:Drug
n3:description
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.
n3:dosage
n28:271B5B4C-363D-11E5-9242-09173F13E4C5 n28:271B5B4D-363D-11E5-9242-09173F13E4C5 n28:271B5B4E-363D-11E5-9242-09173F13E4C5 n28:271B5B4F-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Malhotra S, Shafiq N, Pandhi P: COX-2 inhibitors: a CLASS act or Just VIGORously promoted. MedGenMed. 2004 Mar 23;6(1):6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15208519 # Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS: Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: A randomized controlled trial. Celecoxib Long-term Arthritis Safety Study. JAMA. 2000 Sep 13;284(10):1247-55. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10979111 # Solomon SD, McMurray JJ, Pfeffer MA, Wittes J, Fowler R, Finn P, Anderson WF, Zauber A, Hawk E, Bertagnolli M: Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention. N Engl J Med. 2005 Mar 17;352(11):1071-80. Epub 2005 Feb 15. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15713944 # Yelland MJ, Nikles CJ, McNairn N, Del Mar CB, Schluter PJ, Brown RM: Celecoxib compared with sustained-release paracetamol for osteoarthritis: a series of n-of-1 trials. Rheumatology (Oxford). 2007 Jan;46(1):135-40. Epub 2006 Jun 15. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16777855 # Bertagnolli MM, Eagle CJ, Zauber AG, Redston M, Solomon SD, Kim K, Tang J, Rosenstein RB, Wittes J, Corle D, Hess TM, Woloj GM, Boisserie F, Anderson WF, Viner JL, Bagheri D, Burn J, Chung DC, Dewar T, Foley TR, Hoffman N, Macrae F, Pruitt RE, Saltzman JR, Salzberg B, Sylwestrowicz T, Gordon GB, Hawk ET: Celecoxib for the prevention of sporadic colorectal adenomas. N Engl J Med. 2006 Aug 31;355(9):873-84. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16943400 # FDA label # Sandberg M, Yasar U, Stromberg P, Hoog JO, Eliasson E: Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase. Br J Clin Pharmacol. 2002 Oct;54(4):423-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12392591
n3:group
approved investigational
n3:halfLife
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.
n3:indication
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
n3:manufacturer
n12:271B5B47-363D-11E5-9242-09173F13E4C5
owl:sameAs
n9:DB00482 n22:DB00482
dcterms:title
Celecoxib
adms:identifier
n6:Celecoxib n10:2662 n11:46505596 n13:CEL n14:PA448871 n15:D00567 n16:0025-1515-01 n17:C07589 n18:2562 n19:DB00482 n20:11639 n21:3520
n3:mechanismOfAction
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.
n3:packager
n12:271B5B29-363D-11E5-9242-09173F13E4C5 n12:271B5B2A-363D-11E5-9242-09173F13E4C5 n12:271B5B2D-363D-11E5-9242-09173F13E4C5 n12:271B5B2E-363D-11E5-9242-09173F13E4C5 n12:271B5B2B-363D-11E5-9242-09173F13E4C5 n12:271B5B2C-363D-11E5-9242-09173F13E4C5 n12:271B5B31-363D-11E5-9242-09173F13E4C5 n12:271B5B32-363D-11E5-9242-09173F13E4C5 n12:271B5B2F-363D-11E5-9242-09173F13E4C5 n12:271B5B30-363D-11E5-9242-09173F13E4C5 n12:271B5B35-363D-11E5-9242-09173F13E4C5 n12:271B5B36-363D-11E5-9242-09173F13E4C5 n12:271B5B33-363D-11E5-9242-09173F13E4C5 n12:271B5B34-363D-11E5-9242-09173F13E4C5 n12:271B5B39-363D-11E5-9242-09173F13E4C5 n12:271B5B3A-363D-11E5-9242-09173F13E4C5 n12:271B5B37-363D-11E5-9242-09173F13E4C5 n12:271B5B38-363D-11E5-9242-09173F13E4C5 n12:271B5B3D-363D-11E5-9242-09173F13E4C5 n12:271B5B3E-363D-11E5-9242-09173F13E4C5 n12:271B5B3B-363D-11E5-9242-09173F13E4C5 n12:271B5B3C-363D-11E5-9242-09173F13E4C5 n12:271B5B41-363D-11E5-9242-09173F13E4C5 n12:271B5B42-363D-11E5-9242-09173F13E4C5 n12:271B5B3F-363D-11E5-9242-09173F13E4C5 n12:271B5B40-363D-11E5-9242-09173F13E4C5 n12:271B5B45-363D-11E5-9242-09173F13E4C5 n12:271B5B46-363D-11E5-9242-09173F13E4C5 n12:271B5B43-363D-11E5-9242-09173F13E4C5 n12:271B5B44-363D-11E5-9242-09173F13E4C5
n3:patent
n7:5972986 n7:2177576 n7:2267186 n7:5466823
n3:routeOfElimination
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.
n3:synonym
Celebrex P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide Celecoxib Célécoxib Celecoxibum
n3:toxicity
Symptoms of overdose include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.
n3:volumeOfDistribution
Apparent volume of distribution at steady state (Vdss/F), 200 mg single dose, healthy subjects = 429 L
n26:hasAHFSCode
n29:28-08-04-08
n3:foodInteraction
Take without regard to meals. Taking this product with a high-fat meal will delay the Cmax, but total absorption will be increased by 10 to 20%.
n3:mixture
n31:271B5B28-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
97%, primarily to albumin and, to a lesser extent, a<sub>1</sub>-acid glycoprotein. Celecoxib is not preferentially bound to red blood cells.
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Celecoxib.htm
n32:hasConcept
n33:M0276185
foaf:page
n24:coxib.htm n30:celecoxib.html
n3:IUPAC-Name
n4:271B5B54-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5B5A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5B59-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5B56-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5B57-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5B58-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5B52-363D-11E5-9242-09173F13E4C5 n4:271B5B6A-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5B53-363D-11E5-9242-09173F13E4C5 n4:271B5B50-363D-11E5-9242-09173F13E4C5 n4:271B5B6C-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5B51-363D-11E5-9242-09173F13E4C5
n26:hasATCCode
n27:L01XX33 n27:M01AH01
n3:H-Bond-Acceptor-Count
n4:271B5B60-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5B61-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5B5B-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5B5C-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5B5E-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5B5D-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5B5F-363D-11E5-9242-09173F13E4C5
n3: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%.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
169590-42-5
n3:clearance
Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr.
n3:containedIn
n34:271B5B48-363D-11E5-9242-09173F13E4C5 n34:271B5B49-363D-11E5-9242-09173F13E4C5 n34:271B5B4A-363D-11E5-9242-09173F13E4C5 n34:271B5B4B-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5B66-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5B68-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5B69-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5B6B-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5B65-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5B64-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5B67-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5B55-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5B62-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5B63-363D-11E5-9242-09173F13E4C5