Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H14F3N3O2S |
Molecular Weight | 381.372 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(N)(=O)=O)C(F)(F)F
InChI
InChIKey=RZEKVGVHFLEQIL-UHFFFAOYSA-N
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)
Molecular Formula | C17H14F3N3O2S |
Molecular Weight | 381.372 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/celecoxib.html
http://www.wikidoc.org/index.php/Celecoxib
http://www.rxlist.com/celebrex-drug.htm
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/celecoxib.html
http://www.wikidoc.org/index.php/Celecoxib
http://www.rxlist.com/celebrex-drug.htm
Celecoxib is a nonsteroidal anti-inflammatory drug (NSAID). It works by reducing hormones that cause inflammation and pain in the body. Celecoxib is an analgesic that is FDA approved for the treatment of osteoarthritis,rheumatoid arthritis,juvenile rheumatoid arthritis, ankylosing, spondylitis, acute pain and primary dysmenorrhea. The mechanism of action of Celecoxib is believed to be due to inhibition of prostaglandin synthesis, primarily via inhibition of cyclooxygenase-2 (COX-2). Concomitant use of Celecoxib and analgesic doses of aspirin is not generally recommended. Concomitant use with Celecoxib may diminish the antihypertensive effect of ACE Inhibitors, Angiotensin Receptor Blockers (ARB), or BetaBlockers and can increase serum concentration and prolong half-life of digoxin. Common adverse reactions include hypertension, diarrhea, nausea and headache.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 |
15.0 µM [IC50] | ||
Target ID: CHEMBL230 |
0.04 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
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Palliative | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
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Palliative | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
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Palliative | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
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Primary | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
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Palliative | CELEBREX Approved UseCarefully consider the potential benefits and risks of celecoxib capsules and other treatment options before deciding to use celecoxib capsules. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals [see Warnings and Precautions (5) Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
705 ng/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CELECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
1234 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12426512 |
250 mg/m² single, oral dose: 250 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
CELECOXIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
352.6 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02413203 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
CELECOXIB plasma | Homo sapiens |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7709 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12426512 |
250 mg/m² single, oral dose: 250 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
CELECOXIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.2 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CELECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
3.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12426512 |
250 mg/m² single, oral dose: 250 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
CELECOXIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
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. | 2000 Sep 13 |
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Economic evaluation of celecoxib, a new cyclo-oxygenase 2 specific inhibitor, in Switzerland. | 2001 |
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[The coxibs, third generation anti-inflammatories]. | 2001 Apr |
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Exacerbation of inflammatory bowel disease associated with use of celecoxib. | 2001 Apr |
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Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis. | 2001 Apr |
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Evidence for a direct role of cyclo-oxygenase 2 in implant wear debris-induced osteolysis. | 2001 Apr |
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Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. | 2001 Apr |
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COX-2 inhibitors. | 2001 Apr 2 |
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Liquid chromatographic-mass spectrometric determination of celecoxib in plasma using single-ion monitoring and its use in clinical pharmacokinetics. | 2001 Apr 5 |
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Efficacy and tolerability of celecoxib versus hydrocodone/acetaminophen in the treatment of pain after ambulatory orthopedic surgery in adults. | 2001 Feb |
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Comparison of once-daily and twice-daily administration of celecoxib for the treatment of osteoarthritis of the knee. | 2001 Feb |
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Successful use of cyclooxygenase-2 inhibitor in a patient with aspirin-induced asthma. | 2001 Feb |
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FDA refuses companies' request to drop ulcer warning. | 2001 Feb 17 |
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Gastrointestinal toxic side effects of nonsteroidal anti-inflammatory drugs and cyclooxygenase-2-specific inhibitors. | 2001 Feb 19 |
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Efficacy of cyclooxygenase-2-specific inhibitors. | 2001 Feb 19 |
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Celecoxib--a rational alternative to NSAIDs. | 2001 Jan |
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Celecoxib in patients with asthma and aspirin intolerance. The Celecoxib in Aspirin-Intolerant Asthma Study Group. | 2001 Jan 11 |
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Pharmacokinetics of celecoxib in the presence and absence of interferon-induced acute inflammation in the rat: application of a novel HPLC assay. | 2001 Jan-Apr |
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A new class of COX-2 inhibitors offer an alternative to NSAIDS in pain management after spinal surgery. | 2001 Jul 1 |
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Acute renal failure related to high-dose celecoxib. | 2001 Jul 3 |
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Drug Points: Cholestatic hepatitis in association with celecoxib. | 2001 Jul 7 |
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Celecoxib-- the debate ranges on. | 2001 Jun |
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Celecoxib--the debate rages on. | 2001 Jun |
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Possible celecoxib-induced gastroduodenal ulceration. | 2001 Jun |
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Cyclooxygenase-2: a target for the prevention and treatment of breast cancer. | 2001 Jun |
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Targeting cyclooxygenase 2 and HER-2/neu pathways inhibits colorectal carcinoma growth. | 2001 Jun |
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Rationale for the observed COX-2/COX-1 selectivity of celecoxib from Monte Carlo simulations. | 2001 Jun 18 |
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[Safety of specific cyclo-oxygenase 2 inhibitors]. | 2001 Jun 2 |
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Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors. | 2001 Mar |
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Preventing gastrointestinal complications of NSAIDs. Risk factors, recent advances, and latest strategies. | 2001 May |
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Cyclooxygenase 2 inhibitors and thrombogenicity production: comment on the article by Crofford et al. | 2001 May |
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EULAR recommendations for the management of knee osteoarthritis. | 2001 May |
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Non-steroidal anti-inflammatory drugs with activity against either cyclooxygenase 1 or cyclooxygenase 2 inhibit colorectal cancer in a DMH rodent model by inducing apoptosis and inhibiting cell proliferation. | 2001 May |
Sample Use Guides
Osteoarthritis: 200 mg once daily or 100 mg twice daily
Rheumatoid Arthritis: 100 to 200 mg twice daily
Juvenile Rheumatoid Arthritis: 50 mg twice daily in patients 10-25 kg. 100 mg twice daily in patients more than 25 kg
Ankylosing Spondylitis: 200 mg once daily single dose or 100 mg twice daily. If no effect is observed after 6 weeks, a trial of 400 mg (single or divided doses) may be of benefit
Acute Pain and Primary Dysmenorrhea: 400 mg initially, followed by 200 mg dose if needed on first day. On subsequent days, 200 mg twice daily as needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26438728
The CAR47 and H295R lines showed similar responses that were significantly different from HEK293 at 1 uM, 3 uM, 4uM and 7 uM concentrations of Celecoxib. Increasing Celecoxib concentrations led to decreasing cell numbers with the CAR47 and H295R lines with fewer cells compared to HEK293. In addition, Celecoxib concentrations more than 2 uM reduced cortisol concentrations in H295R cell culture medium.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:56:02 GMT 2023
by
admin
on
Fri Dec 15 15:56:02 GMT 2023
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Record UNII |
JCX84Q7J1L
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QL01XX33
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NDF-RT |
N0000175721
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LIVERTOX |
NBK548579
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EU-Orphan Drug |
EU/3/01/070
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WHO-VATC |
QM01AH01
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EMA ASSESSMENT REPORTS |
ONSENAL (WITHDRAWN: ADENOMATOUS POLYPOSIS COLI)
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FDA ORPHAN DRUG |
718519
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FDA ORPHAN DRUG |
549716
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NDF-RT |
N0000000160
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NCI_THESAURUS |
C80509
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WHO-ATC |
M01AH01
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NDF-RT |
N0000175722
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WHO-ATC |
L01XX33
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FDA ORPHAN DRUG |
751420
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1098504
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JCX84Q7J1L
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CELECOXIB
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DTXSID0022777
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DB00482
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140587
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II-37
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Celecoxib
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7767
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JCX84Q7J1L
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758624
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m3228
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C1728
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2892
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CHEMBL118
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100000089391
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568
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7038
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C105934
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169590-42-5
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719627
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41423
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SUB01143MIG
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
less than 2% of the dose
MINOR
URINE
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METABOLITE -> PARENT |
1-3% in plasma
MINOR
PLASMA
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METABOLITE -> PARENT |
In urine and feces, representing 18.8 and 54.4% of the dose, respectively.
MAJOR
FECAL; URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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