| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
COX-2/cyclooxygenase-2 (IC50 = 32 nM)
Desmethyl Celecoxib targets cyclooxygenase-2 (COX-2), the same enzyme targeted by Celecoxib. COX-2 is an inducible enzyme that catalyzes the conversion of arachidonic acid to prostaglandins, which are mediators of inflammation and pain. Desmethyl Celecoxib is a selective COX-2 inhibitor with an IC50 of 32 nM and exhibits anti-inflammatory activities. As a demethylated analog of Celecoxib, it lacks the methyl group present in the parent drug. |
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| ln Vitro |
Monte Carlo (MC)-extended linear response (ELR) calculations have been used for prediction of binding affinities of celecoxib analogues with the COX-2 enzyme. Three physically motivated descriptors from the MC simulations were used in a regression equation to fit 45 experimental activities with r(2)=0.71 and q(2)=0.68. The ELR approach provides a promising screen for optimization of enzyme inhibitors [1].
In vitro studies have demonstrated that Desmethyl Celecoxib is a selective COX-2 inhibitor with an IC50 of 32 nM. It exhibits anti-inflammatory activities. As a demethylated analog and primary metabolite of Celecoxib, it contributes to the overall pharmacological profile of the parent drug. The compound is used as a research tool for studying COX-2 inhibition and inflammation. Further detailed in vitro characterization data are available. |
| ln Vivo |
In vivo studies of Desmethyl Celecoxib are conducted in the context of Celecoxib metabolism and pharmacology. As a primary metabolite of Celecoxib, it is formed in vivo following Celecoxib administration. Its COX-2 inhibitory activity (IC50 = 32 nM) contributes to the anti-inflammatory effects of the parent drug. The compound is used in pharmacokinetic and pharmacodynamic studies of Celecoxib and its metabolites.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for Desmethyl Celecoxib typically involve COX-2 inhibition studies using recombinant human COX-2. The enzyme is incubated with increasing concentrations of Desmethyl Celecoxib (0.01 nM - 10 μM) and a substrate (e.g., arachidonic acid) in assay buffer at 37°C for 30-60 minutes. Prostaglandin production is measured by ELISA or by quantifying the oxygen consumption or peroxide production. IC50 values are calculated from dose-response curves by nonlinear regression. Selectivity for COX-2 over COX-1 is assessed using recombinant COX-1 in similar assays. Celecoxib is used as a positive control.
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| Cell Assay |
For in vitro cell-based assays, cells expressing COX-2 (e.g., LPS-stimulated macrophages) are cultured in appropriate media. Cells are treated with Desmethyl Celecoxib at concentrations ranging from 0.01-10 μM for 24-72 hours. COX-2 inhibition is assessed by measuring prostaglandin E2 (PGE2) production in culture supernatants by ELISA. Cell viability is assessed by MTT or CCK-8 assays. Anti-inflammatory activity is confirmed by measuring other inflammatory mediators such as TNF-α, IL-6, and NO. The compound's selectivity for COX-2 over COX-1 can be confirmed using cells expressing COX-1.
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| Animal Protocol |
In vivo animal studies with Desmethyl Celecoxib are limited, as the compound is primarily studied as a metabolite of Celecoxib. Anti-inflammatory activity can be assessed in animal models of inflammation (e.g., carrageenan-induced paw edema). The compound would be administered orally or intraperitoneally at doses determined from pharmacokinetic studies. Inflammatory markers and PGE2 levels would be measured in serum or tissue. The compound's effects on pain and inflammation would be assessed. However, specific published protocols are limited.
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| ADME/Pharmacokinetics |
Desmethyl Celecoxib has a molecular weight of 367.35 g/mol and molecular formula C16H12F3N3O2S. Chemical name: 4-[5-(4-aminophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide. The compound is a demethylated analog and primary metabolite of Celecoxib. It is also known as CAY10452 or PTPBS. Pharmacokinetic properties are similar to other COX-2 inhibitors. The compound is intended for research purposes only.
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| Toxicity/Toxicokinetics |
Desmethyl Celecoxib is a selective COX-2 inhibitor with an IC50 of 32 nM. As a COX-2 inhibitor, it is expected to have a similar side effect profile to Celecoxib, including gastrointestinal effects and potential cardiovascular risks at high doses. The compound is used in very small quantities as a research reagent and does not pose significant toxicity risks under normal handling. The compound is not intended for human therapeutic use.
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| References |
[1]. An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors. Organic Process Research & Development. Org. Process Res. Dev. 2019, 23, 9, 1892–1899. https://doi.org/10.1021/acs.oprd.9b00212
[2]. Estimation of binding affinities for celecoxib analogues with COX-2 via Monte Carlo-extended linear response. Bioorg Med Chem Lett . 2002 Feb 11;12(3):267-70. |
| Additional Infomation |
Integrated continuous manufacturing has become a promising approach for the rapid production of active pharmaceutical ingredients (APIs). This paper reports a newly designed continuous flow micro-total process system platform for the rapid production of the selective nonsteroidal anti-inflammatory drug celecoxib. This method has proven to be universally applicable to the synthesis of a variety of alkyl and aryl substituted pyrazoles. To minimize the cumbersome post-processing of potential reaction intermediates/products, we developed a continuous flow extraction separation platform to complete the entire reaction sequence, thereby achieving good yields in a short residence time. The process is further extended to the continuous flow synthesis of COX-2-related APIs (i.e., celecoxib) at the gram scale. [1]
Desmethyl Celecoxib (also known as CAY10452 or PTPBS) is a demethylated analog and primary metabolite of the selective COX-2 inhibitor Celecoxib. It has a molecular weight of 367.35 g/mol and molecular formula C16H12F3N3O2S. Desmethyl Celecoxib is a selective COX-2 inhibitor with an IC50 of 32 nM and exhibits anti-inflammatory activities. The compound is not FDA-approved and is intended for research use only. |
| Molecular Formula |
C16H12N3O2F3S
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|---|---|
| Molecular Weight |
367.34558
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| Exact Mass |
367.06
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| CAS # |
170569-87-6
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| Related CAS # |
Celecoxib-d4;544686-20-6; 169590-42-5
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| PubChem CID |
6426663
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
522.5±60.0 °C at 760 mmHg
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| Flash Point |
269.8±32.9 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.613
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| LogP |
3.75
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
25
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| Complexity |
550
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
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| InChi Key |
MQPLMBSDWYIIID-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H12F3N3O2S/c17-16(18,19)15-10-14(11-4-2-1-3-5-11)22(21-15)12-6-8-13(9-7-12)25(20,23)24/h1-10H,(H2,20,23,24)
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| Chemical Name |
4-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
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| Synonyms |
Desmethyl Celecoxib; 170569-87-6; 4-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide; 1-HEXADECANOYL-2-(P-NITROPHENOXYSUCCINOYL)-SN-GLYCERYL-3-PHOSPHORYLCHOLINE; 4-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide; CHEMBL29920; 4-(5-Phenyl-3-trifluoromethyl-1H-pyrazol-1-yl)benzenesulfonamide; Benzenesulfonamide, 4-[5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-;
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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) |
DMSO : ~250 mg/mL (~680.55 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7222 mL | 13.6110 mL | 27.2220 mL | |
| 5 mM | 0.5444 mL | 2.7222 mL | 5.4444 mL | |
| 10 mM | 0.2722 mL | 1.3611 mL | 2.7222 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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