DuP-697 - CAS 88149-94-4
Catalog number:
88149-94-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C17H12BrFO2S2
Molecular Weight:
411.3
COA:
Inquire
Targets:
Cox-2
Description:
A selective COX-2 inhibitor
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Brife Description:
A selective COX-2 inhibitor
Appearance:
A crystalline solid
Synonyms:
5-bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)-thiophene
Solubility:
Soluble to 100 mM in DMSO
Storage:
Store at -20°C
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
InChIKey:
AJFTZWGGHJXZOB-UHFFFAOYSA-N
InChI:
1S/C17H12BrFO2S2/c1-23(20,21)14-8-4-11(5-9-14)15-10-16(18)22-17(15)12-2-6-13(19)7-3-12/h2-10H,1H3
Canonical SMILES:
Fc1ccc(cc1)c1sc(Br)cc1c1ccc(cc1)S(=O)(=O)C
1.In vitro effects of cyclooxygenase inhibitors in whole blood of horses, dogs, and cats.
Brideau C1, Van Staden C, Chan CC. Am J Vet Res. 2001 Nov;62(11):1755-60.
OBJECTIVE: To determine potency and selectivity of nonsteroidal anti-inflammatory drugs (NSAID) and cyclooxygenase- (COX-) specific inhibitors in whole blood from horses, dogs, and cats.
2.Prenatal effects of DuP-697-the irreversible, highly selective cyclooxygenase-2 inhibitor.
Burdan F1, Dudka J, Szumilo J, Korobowicz A, Klepacz L. Reprod Toxicol. 2003 Jul-Aug;17(4):413-9.
DuP-697 (5-bromo-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-thiophene), like celecoxib and rofecoxib, is a vicinal diaryl heterocycle highly selective cyclooxygenase-2 (COX-2) inhibitor. The aim of the study was to evaluate prenatal tolerability of DuP-697. The drug was administered orally in Tween 80 water suspension once a day to pregnant Wistar rats, on Days 7-18 of gestation. The initial dose, similar to the rat antipyretic dose, was set at 0.05 mg/kg. The middle dose, 3.5 mg/kg, corresponded to the rat anti-inflammatory and analgesic dose. The high dose was set at 35.0 mg/kg. Control animals received Tween 80 water suspension. On Day 21 of gestation, fetuses were delivered by laparotomy and double stained with alcian blue and alizarin red S or examined using the Wilson technique. Intrauterine growth retardation occurred in the groups exposed to the middle and highest dose of DuP-697. Minimal reactive and degenerative hepatic changes were found in both drug-exposed and control groups.
3.Simultaneous quantification of an anti-inflammatory compound (DuP 697) and a potential metabolite (X6882) in human plasma and urine by high-performance liquid chromatography.
Joshi AS1, Raghavan N, Williams RM, Takahashi K, Shingu H, King SY. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):143-50.
A high-performance liquid chromatographic (HPLC) method using fluorescence detection has been developed for the simultaneous analysis of low nanogram concentrations of an anti-inflammatory drug, 5-Bromo-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (DuP 697), and a potential metabolite (X6882) in human plasma and of DuP 697 in human urine. This assay method used an EM Separations Lichrospher C18 endcapped column. The mobile phase was acetonitrile-water (75:25, v/v). The detection of DuP 697 and X6882 was by fluorescence at excitation and emission wavelengths of 256 and 419 nm, respectively. The chromatographic system could separate DuP 697 from X6882, the external standard (anthracene), and other endogenous substances present in human plasma. In human plasma the limits of quantification for DuP 697 and X6882 were 3 and 20 ng/ml, respectively; the limit of quantification for DuP 697 in human urine was 5 ng/ml. These compounds were shown to be stable in frozen (-20 degrees C) human plasma and urine for at least 9 weeks.
4.Studies on anti-inflammatory agents. VI. Synthesis and pharmacological properties of 2,3-diarylthiophenes.
Tsuji K1, Nakamura K, Ogino T, Konishi N, Tojo T, Ochi T, Seki N, Matsuo M. Chem Pharm Bull (Tokyo). 1998 Feb;46(2):279-86.
A series of novel 5-substituted-2,3-diarylthiophenes has been synthesized and found to be active in the rat adjuvant arthritis (AA) model and/or in the yeast-induced hyperalgesia (Randall-Selitto) assay. Among the compounds synthesized herein, 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiop hene (6a) exhibited the most potent activities on AA, collagen-induced arthritis (CIA) and the delayed-type hypersensitivity response to type II collagen. 5-Bromo-2-[4-(methylamino)phenyl]-3-[4-(methylsulfinyl)phenyl]thiophene (38) is also a potent inhibitor of AA, CIA, hyperalgesia and in vitro tumor necrosis factor-alpha production.
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Chemical Structure

CAS 88149-94-4 DuP-697

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