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Merck
CN

D7196

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
NACRES:
NA.77
PubChem Substance ID:
329798845
UNSPSC Code:
12352200
MDL number:
MFCD19443858
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

2,5-Dimethyl-celecoxib, ≥98% (HPLC)

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)

SMILES string

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

InChI key

NTFOSUUWGCDXEF-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

Quality Level

100

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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 analog devoid of COX-2 inhibitor activity, induces apoptosis by inhibiting expression of survivin.
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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000175164
0000140516
0000140516
0000175164
0000141183

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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)
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)
Meghan A Bowler et al.
JACC. Basic to translational science, 4(2), 135-143 (2019-05-08)
Calcific aortic valve disease is a progressive fibrocalcific process that can only be treated with valve replacement. Cadherin-11 has recently been identified as a potential therapeutic target for calcific aortic valve disease. The already approved drug celecoxib, a cyclooxygenase-2 inhibitor
Trial of celecoxib in amyotrophic lateral sclerosis
Cudkowicz ME, et al.
Annals of Neurology, 60(1), 22-31 (2006)
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