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Purity: ≥98%
| Targets |
DuP-697 targets the cyclooxygenase-2 (COX-2) enzyme. COX-2 is an inducible enzyme that is upregulated during inflammation and is responsible for the production of prostaglandins that mediate pain and inflammation. DuP-697 selectively inhibits COX-2 over COX-1, which is the constitutive enzyme involved in gastric mucosal protection.
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| ln Vitro |
Treatment of HT29 cells with DuP-697 (0-100 nM; 24 hours) demonstrated anti-proliferative effects with an IC50 value of 42.8 nM [1]. HT29 cells treated with DuP-697 (25-100 nM; 72 hours) undergo concentration-dependent apoptosis. UR (apoptotic fraction) area as a proportion of total area grew progressively with increasing DuP-697 concentration, from 7% in the control to 52% in 100 nM DuP-697 [1]. At doses of 100, 10, and 1 nM, DuP-697 exhibited anti-angiogenic properties. According to DuP-697, the anti-angiogenic scores are 1.2, 0.8, and 0.5, respectively[1].
In vitro, DuP-697 selectively inhibits COX-2 activity. Its IC50 for COX-2 is in the low nanomolar range, while its IC50 for COX-1 is significantly higher, demonstrating its selectivity. This selectivity is the basis for its reduced gastrointestinal toxicity profile. |
| ln Vivo |
In rats with both confirmed and suspected adjuvant arthritis, DuP-697 is a strong inhibitor of paw swelling (ED50 0.03 and 0.18 mg/kg/day, respectively). In the Randall-Selitto assay, DuP-697 has analgesic effects on inflammation-related pain (ED50 = 3.5 mg/kg) and is a very effective antipyretic medication (ED50 = 0.05 mg/kg). However, it has no effect on benzoquinone writhing in rats (ED50 larger than 100 mg/kg). In volume-depleted rats pretreated with furosemide, DuP-697 (5 mg/kg iv) does not change renal blood flow or renal vascular responses to angiotensin II [2]. DuP-697 is not effective on rat kidney prostaglandin (PG) synthesis, but it is a powerful inhibitor of PG synthesis in the brain (IC50 = 4.5 μM) and a moderate inhibitor of PG synthesis in bull seminal vesicles (IC50 = 24 μM). (75 μM is the IC50)][2].
In vivo, DuP-697 has demonstrated analgesic and anti-inflammatory activity in animal models. It reduces carrageenan-induced paw edema and other inflammatory responses. Its efficacy is comparable to that of non-selective NSAIDs, but with a better gastrointestinal safety profile. |
| Enzyme Assay |
In vitro enzyme assays for DuP-697 measure its inhibition of COX-1 and COX-2 activity. The enzymes are incubated with arachidonic acid and various concentrations of the inhibitor. Prostaglandin production is measured by ELISA or other methods. IC50 values for both isoforms are calculated to determine selectivity.
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| Cell Assay |
Cell Proliferation Assay[1]
Cell Types: HT29 Cell Tested Concentrations: 0 nM, 12.5 nM, 25 nM, 50 nM, 100 nM Incubation Duration: 24 hrs (hours) Experimental Results: CI values diminished in a concentration-dependent manner. Demonstrated statistically significant cytotoxicity. Apoptosis analysis [1] Cell Types: HT29 cell Tested Concentrations: 25 nM, 50 nM, 100 nM Incubation Duration: 72 hrs (hours) Experimental Results: Caused concentration-dependent apoptosis of HT29 cells. For in vitro cellular assays, cells such as macrophages or fibroblasts are stimulated with LPS to induce COX-2 expression. The cells are treated with DuP-697, and prostaglandin E2 (PGE2) levels in the culture media are measured by ELISA. |
| Animal Protocol |
In vivo animal studies for DuP-697 are conducted in standard models of inflammation and pain, such as the carrageenan-induced paw edema model, the adjuvant-induced arthritis model, and the acetic acid-induced writhing test. The compound is typically administered orally.
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| ADME/Pharmacokinetics |
DuP-697 has a molecular weight of 454.43 g/mol and a molecular formula of C22H17BrO2S2. It is a solid. It is typically stored at -20°C and is soluble in DMSO.
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| Toxicity/Toxicokinetics |
Preclinical toxicity of DuP-697 would have been evaluated in standard toxicology studies. As a selective COX-2 inhibitor, it is expected to have a lower risk of gastrointestinal ulcers compared to non-selective NSAIDs, but may have cardiovascular risks. Comprehensive toxicity data is not widely available in public databases.
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| References |
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| Additional Infomation |
DuP 697 belongs to the thiophene class of compounds.
DuP-697 is a potent and selective COX-2 inhibitor. It was an early research compound in the development of selective COX-2 inhibitors (coxibs). |
| Molecular Formula |
C17H12BRFO2S2
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|---|---|
| Molecular Weight |
411.30838
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| Exact Mass |
409.944
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| CAS # |
88149-94-4
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| PubChem CID |
3177
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
454.1±45.0 °C at 760 mmHg
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| Flash Point |
228.4±28.7 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.621
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| LogP |
3.85
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
491
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
AJFTZWGGHJXZOB-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
5-bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)thiophene
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| Synonyms |
DuP-697 DuP 697 DuP697 S-6907 S 6907 S6907 BFMT
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMF :≥ 54 mg/mL (~131.29 mM)
DMSO : ≥ 15 mg/mL (~36.47 mM) Ethanol :≥ 7 mg/mL (~17.02 mM) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4313 mL | 12.1563 mL | 24.3126 mL | |
| 5 mM | 0.4863 mL | 2.4313 mL | 4.8625 mL | |
| 10 mM | 0.2431 mL | 1.2156 mL | 2.4313 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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