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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
Structure of CELECOXIB

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)

HIDE SMILES / InChI

Molecular Formula C17H14F3N3O2S
Molecular Weight 381.372
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1998
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

1998
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

1998
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

1998
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

1998
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

1998
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
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
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
Economic evaluation of celecoxib, a new cyclo-oxygenase 2 specific inhibitor, in Switzerland.
2001
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
Gastrointestinal damage induced by celecoxib and rofecoxib in rats.
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
Trial endpoints for drug approval in oncology: Chemoprevention.
2001 Apr
Middermal elastolysis in two patients with lupus erythematosus.
2001 Apr
Liquid chromatographic-mass spectrometric determination of celecoxib in plasma using single-ion monitoring and its use in clinical pharmacokinetics.
2001 Apr 5
Efficacy and tolerability of celecoxib versus hydrocodone/acetaminophen in the treatment of pain after ambulatory orthopedic surgery in adults.
2001 Feb
Comparison of once-daily and twice-daily administration of celecoxib for the treatment of osteoarthritis of the knee.
2001 Feb
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.
2001 Feb
FDA refuses companies' request to drop ulcer warning.
2001 Feb 17
Efficacy of cyclooxygenase-2-specific inhibitors.
2001 Feb 19
Celecoxib--a rational alternative to NSAIDs.
2001 Jan
Efficacy of celecoxib, a cyclooxygenase 2-specific inhibitor, in the treatment of ankylosing spondylitis: a six-week controlled study with comparison against placebo and against a conventional nonsteroidal antiinflammatory drug.
2001 Jan
Hyaluronan-induced cyclooxygenase-2 expression promotes thromboxane A2 production by renal cells.
2001 Jan
Celecoxib in patients with asthma and aspirin intolerance. The Celecoxib in Aspirin-Intolerant Asthma Study Group.
2001 Jan 11
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
Renal effects of COX-2-selective inhibitors.
2001 Jan-Feb
Cyclooxygenase-selective inhibition of prostanoid formation: transducing biochemical selectivity into clinical read-outs.
2001 Jul
Celecoxib loses its anti-inflammatory efficacy at high doses through activation of NF-kappaB.
2001 Jul
Effect of cyclooxygenase-2 inhibitor (celecoxib) on the infarcted heart in situ.
2001 Jul
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
Rationale for the observed COX-2/COX-1 selectivity of celecoxib from Monte Carlo simulations.
2001 Jun 18
Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors.
2001 Mar
Functional status and health-related quality of life of elderly osteoarthritic patients treated with celecoxib.
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:02 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:02 GMT 2023
Record UNII
JCX84Q7J1L
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
Common Name English
CELECOXIB [MI]
Common Name English
CELECOXIB [EMA EPAR]
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 Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
LIVERTOX NBK548579
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
EU-Orphan Drug EU/3/01/070
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
WHO-VATC QM01AH01
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
EMA ASSESSMENT REPORTS ONSENAL (WITHDRAWN: ADENOMATOUS POLYPOSIS COLI)
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
FDA ORPHAN DRUG 718519
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
FDA ORPHAN DRUG 549716
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
NDF-RT N0000000160
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
NCI_THESAURUS C80509
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
WHO-ATC M01AH01
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
WHO-ATC L01XX33
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
FDA ORPHAN DRUG 751420
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1098504
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
DAILYMED
JCX84Q7J1L
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
WIKIPEDIA
CELECOXIB
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022777
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
DRUG BANK
DB00482
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
RXCUI
140587
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY RxNorm
USAN
II-37
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
LACTMED
Celecoxib
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
INN
7767
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PRIMARY
FDA UNII
JCX84Q7J1L
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
NSC
758624
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
MERCK INDEX
m3228
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C1728
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
IUPHAR
2892
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PRIMARY
ChEMBL
CHEMBL118
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
SMS_ID
100000089391
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
DRUG CENTRAL
568
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
PUBCHEM
2662
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
HSDB
7038
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
MESH
C105934
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
CAS
169590-42-5
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
NSC
719627
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
CHEBI
41423
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
EVMPD
SUB01143MIG
Created by admin on Fri Dec 15 15:56:02 GMT 2023 , Edited by admin on Fri Dec 15 15:56:02 GMT 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
less than 2% of the dose
MINOR
URINE
METABOLITE -> PARENT
1-3% in plasma
MINOR
PLASMA
METABOLITE -> PARENT
In urine and feces, representing 18.8 and 54.4% of the dose, respectively.
MAJOR
FECAL; URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC