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Details

Stereochemistry ACHIRAL
Molecular Formula C18H16F3N3O2S
Molecular Weight 395.399
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,5-Dimethylcelecoxib

SMILES

CC1=CC(C2=CC(=NN2C3=CC=C(C=C3)S(N)(=O)=O)C(F)(F)F)=C(C)C=C1

InChI

InChIKey=NTFOSUUWGCDXEF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C18H16F3N3O2S
Molecular Weight 395.399
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/21964407 | https://www.ncbi.nlm.nih.gov/pubmed/14973075 | https://www.ncbi.nlm.nih.gov/pubmed/27761963

2,5-dimethyl-celecoxib, also known as DMC, is celecoxib analog that lacks COX-2 inhibitory activity but exhibits anti-tumor properties. DMC demonstrated its ability to inhibit xenograft tumor growth through the inhibition of Akt activation. The central mechanism for the anticancer effect of DMC is the suppression of the Wnt/β-catenin signaling pathway. DMS is a synthetic opener of KV7 channels in smooth muscle cells.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 38.0 µM [IC50]
Inhibitor
8297
 20.0 µM [IC50]
Activator
1430
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents.
2002 Dec 4
Dimethyl-celecoxib (DMC), a derivative of celecoxib that lacks cyclooxygenase-2-inhibitory function, potently mimics the anti-tumor effects of celecoxib on Burkitt's lymphoma in vitro and in vivo.
2005 May
Patents

Patents

US20130331422
1
US8785466 B2
1

Sample Use Guides

In Vivo Use Guide
100-150 mg/kg for 5 days/week over 4 weeks.
Route of Administration: Oral
In Vitro Use Guide
2,5-dimethyl-celecoxib had no COX-2 inhibitory activity (IC50>100 uM) but was highly potent mediator of apoptotic death in PC-3 cells. Exposure of cells to 50 uM 2,5-dimethylcelecoxib resulted in a 50% decrease in cell viability within 1 hour compared with 2 hours for celecoxib.
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:56:08 GMT 2023
Edited
by admin
on Sat Dec 16 19:56:08 GMT 2023
Record UNII
STL56MF6TH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,5-Dimethylcelecoxib
Common Name English
4-[5-(2,5-Dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Systematic Name English
Benzenesulfonamide, 4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
Systematic Name English
Code System Code Type Description
FDA UNII
STL56MF6TH
Created by admin on Sat Dec 16 19:56:08 GMT 2023 , Edited by admin on Sat Dec 16 19:56:08 GMT 2023
PRIMARY
CAS
457639-26-8
Created by admin on Sat Dec 16 19:56:08 GMT 2023 , Edited by admin on Sat Dec 16 19:56:08 GMT 2023
PRIMARY
PUBCHEM
11545682
Created by admin on Sat Dec 16 19:56:08 GMT 2023 , Edited by admin on Sat Dec 16 19:56:08 GMT 2023
PRIMARY
NIH
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