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Details

Stereochemistry ACHIRAL
Molecular Formula C17H14F3N3O2S
Molecular Weight 381.3739
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CELECOXIB

SMILES

Cc1ccc(cc1)-c2cc(C(F)(F)F)nn2-c3ccc(cc3)S(=O)(=O)N

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)

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Palliative
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Palliative
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Palliative
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Primary
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Palliative
CELEBREX

Approved Use

Carefully 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 Date

9.1506239E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
200 mg single, oral
dose: 200 mg
route of administration: oral
experiment type: single
co-administered:
CELECOXIB plasma
Homo sapiens
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7709 μg × h/L
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

PubMed

TitleDatePubMed
Potential adverse effects of cyclooxygenase-2 inhibition: evidence from animal models of inflammation.
2001
Alzheimer's disease, inflammation and non-steroidal anti-inflammatory drugs.
2001
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis.
2001
Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells.
2001
Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy.
2001
[COX-2 specific inhibitors: are NSAIDs and the stomach become reconcilied?].
2001 Apr
Celecoxib--the debate rages on.
2001 Apr
[The coxibs, third generation anti-inflammatories].
2001 Apr
Inhibition of cyclooxygenase-1 or -2 on insulin sensitivity in healthy subjects.
2001 Apr
[Effect of celecoxib, a COX-2 inhibitor, in familial adenomatous polyposis].
2001 Apr
In-vitro metabolism of celecoxib, a cyclooxygenase-2 inhibitor, by allelic variant forms of human liver microsomal cytochrome P450 2C9: correlation with CYP2C9 genotype and in-vivo pharmacokinetics.
2001 Apr
Cyclooxygenase 2 inhibition and thrombosis: comment on the article by Crofford et al.
2001 Apr
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.
2001 Apr
Selective COX-2 inhibitors.
2001 Apr
COX-2 inhibitors.
2001 Apr 2
NSAIDS and selective COX-2 inhibitors: competition between gastroprotection and cardioprotection.
2001 Apr 21
Liquid chromatographic-mass spectrometric determination of celecoxib in plasma using single-ion monitoring and its use in clinical pharmacokinetics.
2001 Apr 5
Celecoxib: a new option in the treatment of arthropathies and familial adenomatous polyposis.
2001 Jan
Anti-inflammatory drugs, cyclooxygenases and other factors.
2001 Jan
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
Cyclooxygenase-2 pathway correlates with VEGF expression in head and neck cancer. Implications for tumor angiogenesis and metastasis.
2001 Jan-Feb
Selective cyclooxygenase-2 inhibitors: a pattern of nephrotoxicity similar to traditional nonsteroidal anti-inflammatory drugs.
2001 Jul
Cyclooxygenase-selective inhibition of prostanoid formation: transducing biochemical selectivity into clinical read-outs.
2001 Jul
Chemoprevention of colorectal cancer.
2001 Jul
Celecoxib loses its anti-inflammatory efficacy at high doses through activation of NF-kappaB.
2001 Jul
Comparative analysis of pharmacologic and/or genetic disruption of cyclooxygenase-1 and cyclooxygenase-2 function in female reproduction in mice.
2001 Jul
Effect of cyclooxygenase-2 inhibitor (celecoxib) on the infarcted heart in situ.
2001 Jul
A new class of COX-2 inhibitors offer an alternative to NSAIDS in pain management after spinal surgery.
2001 Jul 1
Acute renal failure related to high-dose celecoxib.
2001 Jul 3
Drug Points: Cholestatic hepatitis in association with celecoxib.
2001 Jul 7
Celecoxib-- the debate ranges on.
2001 Jun
Celecoxib--the debate rages on.
2001 Jun
Suppression of occurrence and advancement of beta-catenin-accumulated crypts, possible premalignant lesions of colon cancer, by selective cyclooxygenase-2 inhibitor, celecoxib.
2001 Jun
Possible celecoxib-induced gastroduodenal ulceration.
2001 Jun
Cyclooxygenase-2: a target for the prevention and treatment of breast cancer.
2001 Jun
T-cell involvement in drug-induced acute generalized exanthematous pustulosis.
2001 Jun
Evaluation of the tocolytic effect of a selective cyclooxygenase-2 inhibitor in a mouse model of lipopolysaccharide-induced preterm delivery.
2001 Jun
Cyclooxygenase-1 vs. cyclooxygenase-2 inhibitors in the induction of antinociception in rodent withdrawal reflexes.
2001 Jun
Targeting cyclooxygenase 2 and HER-2/neu pathways inhibits colorectal carcinoma growth.
2001 Jun
Rat colorectal tumours treated with a range of non-steroidal anti-inflammatory drugs show altered cyclooxygenase-2 and cyclooxygenase-1 splice variant mRNA expression levels.
2001 Jun
Rationale for the observed COX-2/COX-1 selectivity of celecoxib from Monte Carlo simulations.
2001 Jun 18
[Safety of specific cyclo-oxygenase 2 inhibitors].
2001 Jun 2
Cyclooxygenase-2 inhibition and renal function.
2001 Jun 5
Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors.
2001 Mar
Cyclooxygenase-2--specific inhibitors and cardiorenal function: a randomized, controlled trial of celecoxib and rofecoxib in older hypertensive osteoarthritis patients.
2001 Mar-Apr
Cardiovascular and renal effects of COX-2-specific inhibitors: recent insights and evolving clinical implications.
2001 Mar-Apr
Preventing gastrointestinal complications of NSAIDs. Risk factors, recent advances, and latest strategies.
2001 May
Osteoarthritis. A primary care approach for physicians in 2000 and beyond.
2001 May
Cyclooxygenase 2 inhibitors and thrombogenicity production: comment on the article by Crofford et al.
2001 May
Celecoxib- and rofecoxib-induced delirium.
2001 Spring
Patents

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
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.
Name Type Language
CELECOXIB
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
CELECOXIB [USP MONOGRAPH]
Common Name English
CELECOXIB [INN]
Common Name English
SC-58635
Code English
CONSENSI COMPONENT CELECOXIB
Brand Name English
CELECOXIB [MI]
Common Name English
CELECOXIB [EMA EPAR]
Common Name English
CELECOXIB [WHO-DD]
Common Name English
CELECOXIB [JAN]
Common Name English
CELEBREX
Brand Name English
NSC-719627
Code English
P-(5-P-TOLYL-3-(TRIFLUOROMETHYL)PYRAZOL-1-YL)BENZENESULFONAMIDE
Common Name English
DFN15
Code English
CELECOXIB COMPONENT OF CONSENSI
Brand Name English
CELECOXIB [VANDF]
Common Name English
CELECOXIB [MART.]
Common Name English
ONSENAL
Brand Name English
CELECOXIB [USP-RS]
Common Name English
NSC-758624
Code English
DFN-15
Code English
4-(5-(4-METHYLPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL)BENZENESULFONAMIDE
Systematic Name English
ELYXYB
Brand Name English
CELECOXIB [EP MONOGRAPH]
Common Name English
CELECOXIB [ORANGE BOOK]
Common Name English
CELECOXIB [USAN]
Common Name English
CELECOXIB [HSDB]
Common Name English
Classification Tree Code System Code
WHO-VATC QL01XX33
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
LIVERTOX 176
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
EU-Orphan Drug EU/3/01/070
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
WHO-VATC QM01AH01
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
EMA ASSESSMENT REPORTS ONSENAL (WITHDRAWN: ADENOMATOUS POLYPOSIS COLI)
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
FDA ORPHAN DRUG 718519
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
FDA ORPHAN DRUG 549716
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
NCI_THESAURUS C80509
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
WHO-ATC M01AH01
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
WHO-ATC L01XX33
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
FDA ORPHAN DRUG 751420
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
Code System Code Type Description
WIKIPEDIA
CELECOXIB
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
EPA CompTox
169590-42-5
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
DRUG BANK
DB00482
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
RXCUI
140587
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY RxNorm
LACTMED
Celecoxib
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
INN
7767
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
FDA UNII
JCX84Q7J1L
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
MERCK INDEX
M3228
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C1728
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
IUPHAR
2892
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL118
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
DRUG CENTRAL
568
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
USP_CATALOG
1098504
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY USP-RS
PUBCHEM
2662
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
HSDB
7038
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
MESH
C105934
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
CAS
169590-42-5
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY
EVMPD
SUB01143MIG
Created by admin on Fri Jun 25 21:07:22 UTC 2021 , Edited by admin on Fri Jun 25 21:07:22 UTC 2021
PRIMARY