General
Preferred name
CELECOXIB
Synonyms
SC 58635 ()
Celebrex ()
Celebra ()
Celecox ()
Onsenal ()
Solexa ()
SC-58635 ()
YM-177 ()
YM177 ()
Benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]- ()
PMID26394986-Compound-22 ()
Celecoxib169590-42-5 ()
Celecoxib?(SC 58635) ()
Celebrex, Celebra,SC 58635 ()
DFN15 ()
DFN-15 ()
NSC-719627 ()
NSC-758624 ()
Elyxyb ()
Celecoxib-d7 ()
P&D ID
PD000893
CAS
169590-42-5
544686-21-7
184007-95-2
Tags
natural product
drug
available
Approved by
FDA
First approval
1998
Drug Status
investigational
approved
withdrawn
Drug indication
Rheumatoid arthritis
Pain
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Celecoxib is a non-steroidal anti-inflammatory drug (NSAID).
MOA 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 [FDA label].; ; The mechanism of action of _celecoxib_ is the inhibition of prostaglandin synthesis through COX-2 inhibition [FDA label].; ; COX-2 is expressed heavily in inflamed tissues where it is induced by inflammatory mediators. COX-2 also plays physiological roles in a limited number of tissues, including those of the female reproductive tract, the kidney, and possibly the vascular endothelium [L3296].
METABOLISM Celecoxib metabolism is primarily mediated via _cytochrome P450 2C9_, in the liver. Three metabolites, a primary alcohol, the corresponding _carboxylic acid_ and its _glucuronide conjugate_, have been identified in human plasma. These metabolites are inactive as COX-1 or COX-2 inhibitors. Patients who are known or suspected to be P450 2C9 poor metabolizers, based on a previous history, should be administered celecoxib with caution as they may have abnormally high plasma levels due to their reduced metabolic clearance [FDA label].; ; When celecoxib capsules were taken with a high-fat meal, peak plasma levels were delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20% [FDA label].;
ABSORPTION Easily 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% [FDA label].; ; A meta-analysis of pharmacokinetic studies has suggested an approximately 40% higher AUC (area under the curve) of celecoxib in black patients compared to Caucasians for unknown reasons [L3296].
DESCRIPTION Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) . (GtoPdb)
PHARMACODYNAMICS Celecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). ; The inhibition of prostaglandin E2 synthesis which (a mediator of pain) results from the inhibition of COX-2, and helps to alleviate pain symptoms [FDA label].; ; Celecoxib is used to treat rheumatoid arthritis, osteoarthritis, and familial adenomatous polyposis (FAP). Due to its lack of platelet effects, celecoxib is not a substitute for aspirin for cardiovascular prophylaxis [FDA label].; ;
TOXICITY LD50 in both the rat and dog is >2000 mg/kg [FDA label].; ; It is not advisable to administer celecoxib in patients with renal impairment or advanced hepatic impairment [FDA label].; Symptoms of overdose celecoxib include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting [L3293]. Because serious GI tract ulcerations and bleeding can occur without preceding symptoms, physicians should monitor for signs/symptoms of GI bleeding [FDA label].; ; Multiple studies have been performed on the coadministration of celecoxib and proton pump inhibitors [A34171], [A34172]. It has been concluded that in patients at high risk of both cardiovascular and gastrointestinal events who require concomitant aspirin and NSAID, celecoxib in addition to a proton-pump inhibitor is the preferred treatment to reduce the risk of recurrent episodes of upper gastrointestinal bleeding [A34172].; ; **A note on cardiovascular safety:** ; ; The concerns about the cardiovascular thrombotic risk of COX-2 selective NSAIDS emerged in the early 2000’s. Following an FDA Advisory Committee meeting in 2005, in which data from large clinical outcome trials in a wide range of indications and epidemiology studies of several individual NSAIDs were analyzed, the FDA concluded that the risk for cardiovascular thrombotic events was apparent for both COX-2 selective NSAIDs and nonselective NSAIDs [L3293].; ; Importantly, postmarketing cardiovascular outcomes trial (PRECISION) found that the lowest dose of celecoxib was similar to moderate doses of naproxen and ibuprofen in regards to cardiovascular (CV) safety [L3293]. Patients with recent cardiovascular events such as acute MI, coronary revascularization, or coronary stent placement were not studied in the PRECISION trial. NSAID use is not advisable in these groups of patients [L3293].; ;
DESCRIPTION Selective cyclooxygenase-2 (COX-2) inhibitor (Tocriscreen Plus)
Cell lines
26
Organisms
3
Compound Sets
38
AdooQ Bioactive Compound Library
A10193
Axon Medchem Screening Library
1919
Cayman Chemical Bioactives
10008672
18248
ChEMBL Approved Drugs
CHEMBL118
ChEMBL Drugs
CHEMBL118
Concise Guide to Pharmacology 2017/18
2892
Concise Guide to Pharmacology 2019/20
2892
Concise Guide to Pharmacology 2021/22
2892
Concise Guide to Pharmacology 2023/24
2892
Drug Repurposing Hub
DrugBank
DB00482
DrugBank Approved Drugs
DB00482
DrugCentral
568
DrugCentral Approved Drugs
568
DrugMAP
DM43Z1G
DM6LOQU
DrugMAP Approved Drugs
DM6LOQU
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS101363
Guide to Pharmacology
2892
Ki Database
CELECOXIB
LINCS compound set
10503-101
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL118
LSP-OptimalKinase library (Laboratory of Systems Pharmacology)
CHEMBL118
MedChem Express Bioactive Compound Library
HY-14398
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
JCX84Q7J1L
NIH Approved Oncology Drugs
535138
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Celecoxib
TargetMol Bioactive Compound Library
T0466
The Spectrum Collection
Tocriscreen Plus
3786
Withdrawn 2.0
w205
External IDs
62
Properties
(calculated by RDKit )
Molecular Weight
381.08
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
3
Aromatic Ring Count
3
cLogP
3.51
TPSA
77.98
Fraction CSP3
0.12
Chiral centers
0.0
Largest ring
6.0
QED
0.75
Structural alerts
2
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
Related compounds
Custom attributes
(extracted from source data)
Target Type
Enzymes
Pathway
Immunology/Inflammation
Neuroscience
Target
COX-2
CA12, PDPK1, PTGS2
COX-2 inhibitor
COX
Member status
virtual
MOA
Cyclooxygenase-2 Inhibitors
Angiogenesis Inhibitors
"Cyclooxygenase-2 Inhibitors
Angiogenesis Inhibitors"
cyclooxygenase inhibitor
Indication
osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, primary dysmenorrhea (PD)
Disease Area
rheumatology, endocrinology
ATC
L01XX33
M01AH01
Toxicity type
cardiovascular
Therapeutic Indication
Antiarthritic
Therapeutic Class
Antiinflammatory
Analgesics
Source data