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Merck
CN

35342

2,5-Dimethyl-celecoxib

VETRANAL®, analytical standard

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.24
PubChem Substance ID:
329755121
UNSPSC Code:
41116107
MDL number:
MFCD19443858

Key Documents

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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

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

2,5-Dimethyl-celecoxib is a derivative of the anti-inflammatory drug, celecoxib.

Application

2,5-Dimethyl-celecoxib may be used as an internal standard for the determination of celecoxib in human plasma samples by liquid chromatography coupled to electrospray ionization and time of flight mass spectrometry (LC-ESI-TOF-MS).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

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

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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
BCBS4479V

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Calcium-activated endoplasmic reticulum stress as a major component of tumor cell death induced by 2, 5-dimethyl-celecoxib, a non-coxib analogue of celecoxib.
Pyrko P, et al.
Molecular Cancer Therapeutics, 6(4), 1262-1275 (2007)
Determination of Celecoxib in human plasma using liquid chromatography with high resolution time of flight-mass spectrometry
Dongari N, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 955(4), 86-92 (2014)
Dai Tamura et al.
International journal of oncology, 46(3), 1393-1404 (2015-01-13)
Celecoxib plays antitumor roles via multiple mechanisms in a variety of human cancers. The aim of this study was to clarify the mechanism of action of celecoxib in canine mammary tumors. We examined the antitumor effects of celecoxib in AZACB
So-Jung Kim et al.
Experimental cell research, 330(2), 451-459 (2014-09-15)
In the present study, we investigated whether celecoxib could induce the expression of NKG2D ligands in clonogenic colon cancer cells, and increase their susceptibility to NK cell-mediated cell death. Celecoxib and its non-coxib analog, 2,5-dimethyl celecoxib, induced ULBP-1 and DR5
Mark J Henderson et al.
Molecular biology of the cell, 25(18), 2828-2839 (2014-07-18)
Endoplasmic reticulum (ER) calcium homeostasis is disrupted in diverse pathologies, including neurodegeneration, cardiovascular diseases, and diabetes. Temporally defining calcium dysregulation during disease progression, however, has been challenging. Here we describe secreted ER calcium-monitoring proteins (SERCaMPs), which allow for longitudinal monitoring

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