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D7196

2,5-Dimethyl-celecoxib

Name: 2,5-Dimethyl-celecoxib
Brand: SIGMA

≥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

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Properties

Quality Segment

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

Description

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 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.