CELECOXIB

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf
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
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135032 \| https://www.ncbi.nlm.nih.gov/pubmed/16080279	Inhibitor 8297		15.0 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135032 \| https://www.ncbi.nlm.nih.gov/pubmed/16080279 \| http://www.drugbank.ca/drugs/DB00482	Inhibitor 8297		0.04 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Palliative	Approved 8429	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
Rheumatoid arthritis 316 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Palliative	Approved 8429	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
Juvenile rheumatoid arthritis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Palliative	Approved 8429	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
Ankylosing spondylitis 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Palliative	Approved 8429	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
Acute pain 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Primary	Approved 8429	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 dysmenorrhea 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020998s048lbl.pdf	Palliative	Approved 8429	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

C_max

Value	Dose	Analyte	Population
705 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020998s017lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020998s017lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:41423	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41423
ChemicalBook	CB54842250	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB54842250
ChemicalBook	CB7444681	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7444681
ChemicalBook	CB74842249	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB74842249
ChemicalBook	CB91267649	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB91267649
ChemicalBook	CB93313564	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB93313564
MolPort	MolPort-002-885-815	https://www.molport.com/shop/molecule-link/MolPort-002-885-815
Selleck Chemicals	Celecoxib	http://www.selleckchem.com/products/Celecoxib.html
ZINC	ZINC000002570895	http://zinc15.docking.org/substances/ZINC000002570895
eMolecules	901601	https://www.emolecules.com/cgi-bin/more?vid=901601

PubMed

Title	Date	PubMed
Potential adverse effects of cyclooxygenase-2 inhibition: evidence from animal models of inflammation.	2001	11437671
Alzheimer's disease, inflammation and non-steroidal anti-inflammatory drugs.	2001	11433600
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis.	2001	11398914
Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells.	2001	11384747
Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy.	2001	11330653
[COX-2 specific inhibitors: are NSAIDs and the stomach become reconcilied?].	2001 Apr	11449148
Celecoxib--the debate rages on.	2001 Apr	11402887
[The coxibs, third generation anti-inflammatories].	2001 Apr	11388024
Inhibition of cyclooxygenase-1 or -2 on insulin sensitivity in healthy subjects.	2001 Apr	11383931
[Effect of celecoxib, a COX-2 inhibitor, in familial adenomatous polyposis].	2001 Apr	11367984
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	11337938
Gastrointestinal damage induced by celecoxib and rofecoxib in rats.	2001 Apr	11330413
Exacerbation of inflammatory bowel disease associated with use of celecoxib.	2001 Apr	11316199
Reduced incidence of gastroduodenal ulcers with celecoxib, a novel cyclooxygenase-2 inhibitor, compared to naproxen in patients with arthritis.	2001 Apr	11316141
COX-2 inhibitors.	2001 Apr 2	11346118
NSAIDS and selective COX-2 inhibitors: competition between gastroprotection and cardioprotection.	2001 Apr 21	11418144
Liquid chromatographic-mass spectrometric determination of celecoxib in plasma using single-ion monitoring and its use in clinical pharmacokinetics.	2001 Apr 5	11334356
Renal safety of combined cyclooxygenase 2 (COX-2) inhibitor and angiotensin II receptor blocker administration in mild volume depletion.	2001 Apr 7	11345810
Celecoxib: a new option in the treatment of arthropathies and familial adenomatous polyposis.	2001 Jan	11336575
Anti-inflammatory drugs, cyclooxygenases and other factors.	2001 Jan	11336563
Cyclooxygenase-2 pathway correlates with VEGF expression in head and neck cancer. Implications for tumor angiogenesis and metastasis.	2001 Jan-Feb	11326316
Selective cyclooxygenase-2 inhibitors: a pattern of nephrotoxicity similar to traditional nonsteroidal anti-inflammatory drugs.	2001 Jul	11448662
Cyclooxygenase-selective inhibition of prostanoid formation: transducing biochemical selectivity into clinical read-outs.	2001 Jul	11435450
Chemoprevention of colorectal cancer.	2001 Jul	11429490
Celecoxib loses its anti-inflammatory efficacy at high doses through activation of NF-kappaB.	2001 Jul	11427506
Comparative analysis of pharmacologic and/or genetic disruption of cyclooxygenase-1 and cyclooxygenase-2 function in female reproduction in mice.	2001 Jul	11416042
Effect of cyclooxygenase-2 inhibitor (celecoxib) on the infarcted heart in situ.	2001 Jul	11408829
A new class of COX-2 inhibitors offer an alternative to NSAIDS in pain management after spinal surgery.	2001 Jul 1	11458162
Acute renal failure related to high-dose celecoxib.	2001 Jul 3	11434756
Drug Points: Cholestatic hepatitis in association with celecoxib.	2001 Jul 7	11440939
Celecoxib-- the debate ranges on.	2001 Jun	11455700
Celecoxib--the debate rages on.	2001 Jun	11455699
Suppression of occurrence and advancement of beta-catenin-accumulated crypts, possible premalignant lesions of colon cancer, by selective cyclooxygenase-2 inhibitor, celecoxib.	2001 Jun	11429049
Possible celecoxib-induced gastroduodenal ulceration.	2001 Jun	11408999
Cyclooxygenase-2: a target for the prevention and treatment of breast cancer.	2001 Jun	11397667
T-cell involvement in drug-induced acute generalized exanthematous pustulosis.	2001 Jun	11390425
Evaluation of the tocolytic effect of a selective cyclooxygenase-2 inhibitor in a mouse model of lipopolysaccharide-induced preterm delivery.	2001 Jun	11385116
Cyclooxygenase-1 vs. cyclooxygenase-2 inhibitors in the induction of antinociception in rodent withdrawal reflexes.	2001 Jun	11378164
Targeting cyclooxygenase 2 and HER-2/neu pathways inhibits colorectal carcinoma growth.	2001 Jun	11375952
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	11375891
Rationale for the observed COX-2/COX-1 selectivity of celecoxib from Monte Carlo simulations.	2001 Jun 18	11412976
[Safety of specific cyclo-oxygenase 2 inhibitors].	2001 Jun 2	11414163
Cyclooxygenase-2 inhibition and renal function.	2001 Jun 5	11388824
Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors.	2001 Mar	11318071
Preventing gastrointestinal complications of NSAIDs. Risk factors, recent advances, and latest strategies.	2001 May	11381661
Osteoarthritis. A primary care approach for physicians in 2000 and beyond.	2001 May	11376380
Cyclooxygenase 2 inhibitors and thrombogenicity production: comment on the article by Crofford et al.	2001 May	11352260
EULAR recommendations for the management of knee osteoarthritis.	2001 May	11345080
Surveillance colonoscopy or chemoprevention with COX-2 inhibitors in average-risk post-polypectomy patients: a decision analysis.	2001 May	11328256
Celecoxib- and rofecoxib-induced delirium.	2001 Spring	11449042

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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