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D7196

Sigma-Aldrich

2,5-Dimethyl-celecoxib

≥98% (HPLC)

Synonym(s):

2,5-Dimethylcelecoxib, 4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C18H16F3N3O2S
CAS Number:
457639-26-8
Molecular Weight:
395.40
MDL number:
MFCD19443858
UNSPSC Code:
12352200
PubChem Substance ID:
329798845
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

Cc1ccc(C)c(c1)-c2cc(nn2-c3ccc(cc3)S(N)(=O)=O)C(F)(F)F

InChI

1S/C18H16F3N3O2S/c1-11-3-4-12(2)15(9-11)16-10-17(18(19,20)21)23-24(16)13-5-7-14(8-6-13)27(22,25)26/h3-10H,1-2H3,(H2,22,25,26)

InChI key

NTFOSUUWGCDXEF-UHFFFAOYSA-N

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Application

2,5-Dimethyl-celecoxib has been used
  • To block the synthesis of prostaglandin E2 and to study effect of transforming growth factor-2 signaling towards cyclooxygenase-2 expression.
  • In an in vitro study to analyze its pro-oxidative capacities in metastatic melanoma/ breast cancer cells.
  • To study its interaction between silymarin on chemically induced osteoarthritis in rats.

Biochem/physiol Actions

Celecoxib is a pyrazole derivative containing sulfonamide substituent. It is mostly metabolized by the cytochrome P450 2C9 system. Celecoxib possess anti-inflammatory action and can enhance antidepressant response.
Celecoxib, and the inactive analog 2′,5′-dimethyl celecoxib both induce apoptosis in a many cancer cell lines by down-regulating the expression of survivin. This activiy is mediated via an AKT mediated pathway, and is unique to this class of cyclo-oxygenase inhibitors, as non-selective NSAIDs or other COX-2 specific inhibitors such as rofecoxib, do not effect survivin expression. Unlike celecoxib, 2′,5′-dimethyl celecoxib is devoid of any inhibitory activity against COX-2.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

wgk_germany

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Celecoxib inhibits mitochondrial O 2 consumption, promoting ROS dependent death of murine and human metastatic cancer cells via the apoptotic signalling pathway
Pritchard R, et al.
Biochemical Pharmacology (2018)
Clinical trial of adjunctive celecoxib treatment in patients with major depression: a double-blind and placebo controlled trial
Akhondzadeh S, et al.
Depression and Anxiety, 26(7), 607-611 (2009)
Oncology Nursing Drug Handbook, 521-521 (2004)
Trial of celecoxib in amyotrophic lateral sclerosis
Cudkowicz ME, et al.
Annals of Neurology, 60(1), 22-31 (2006)
Z Ashkavand et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(13), 1200-1205 (2012-08-29)
Silymarin (SMN) is used as an antioxidant complex to attenuate the pro-oxidant effects of toxic agents. This study was carried out to investigate the effect of SMN, Celecoxib (CLX) individually and in combination on monoiodoacetate (MIA)-induced osteoarthritis (OA) in rat.
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