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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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-1 131	Inhibitor 8,504		15.0 µM [IC50]
Cyclooxygenase-2 201	Inhibitor 8,504		0.04 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157	Palliative	Approved 8,583	CELEBREX
Rheumatoid arthritis 320	Palliative	Approved 8,583	CELEBREX
Juvenile rheumatoid arthritis 5	Palliative	Approved 8,583	CELEBREX
Ankylosing spondylitis 33	Palliative	Approved 8,583	CELEBREX
Acute pain 17	Primary	Approved 8,583	CELEBREX
Primary dysmenorrhea 16	Palliative	Approved 8,583	CELEBREX

C_max

Value	Dose	Analyte	Population
352.6 ng/mL	200 mg single, oral	CELECOXIB plasma	Homo sapiens
705 ng/mL	200 mg single, oral	CELECOXIB plasma	Homo sapiens
1234 μg/L	250 mg/m² 2 times / day steady-state, oral	CELECOXIB plasma	Homo sapiens
686.83 ng/mL	200 mg single, oral	CELECOXIB plasma	Homo sapiens
613 μg/mL	200 mg 2 times / day multiple, oral	CELECOXIB plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
7709 μg × h/L	250 mg/m² 2 times / day steady-state, oral	CELECOXIB plasma	Homo sapiens
5911.48 ng × h/mL	200 mg single, oral	CELECOXIB plasma	Homo sapiens
5164 μg × h/mL	200 mg 2 times / day multiple, oral	CELECOXIB plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
11.2 h	200 mg single, oral	CELECOXIB plasma	Homo sapiens
3.7 h	250 mg/m² 2 times / day steady-state, oral	CELECOXIB plasma	Homo sapiens
8.79 h	200 mg single, oral	CELECOXIB plasma	Homo sapiens
6.4 h	200 mg 2 times / day multiple, oral	CELECOXIB plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
3%	200 mg single, oral		CELECOXIB plasma	Homo sapiens

Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 10 entries

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PubMed

Show entries

Title	Date	PubMed
Selective cyclo-oxygenase-2 inhibition with celecoxib elevates blood pressure and promotes leukocyte adherence.	2000 Apr	10742298
The cyclooxygenase-2 inhibitor celecoxib induces apoptosis by blocking Akt activation in human prostate cancer cells independently of Bcl-2.	2000 Apr 14	10753955
Non-steroidal anti-inflammatory drugs with different cyclooxygenase inhibitory profiles that prevent aberrant crypt foci formation but vary in acute gastrotoxicity in a rat model.	2000 Dec	11197048
Alzheimer's disease, inflammation and non-steroidal anti-inflammatory drugs.	2001	11433600
Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells.	2001	11384747

Showing 1 to 5 of 22 entries

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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.