Desmethyl Celecoxib (PTPBS) is an demethylated metabolite of Celecoxib (SC58635; YM-177; SC-58635; YM 177; Celebrex; Xilebao) which is cyclooxygenase-2 (COX-2) inhibitor approved as an anti-inflammatory agent of the NSAID class.
Physicochemical Properties
| Molecular Formula | C16H12N3O2F3S |
| Molecular Weight | 367.34558 |
| Exact Mass | 367.06 |
| CAS # | 170569-87-6 |
| Related CAS # | Celecoxib-d4;544686-20-6; 169590-42-5 |
| PubChem CID | 6426663 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 522.5±60.0 °C at 760 mmHg |
| Flash Point | 269.8±32.9 °C |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.613 |
| LogP | 3.75 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 25 |
| Complexity | 550 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F |
| InChi Key | MQPLMBSDWYIIID-UHFFFAOYSA-N |
| 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) |
| Chemical Name | 4-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide |
| 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]-; |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | COX-2/cyclooxygenase-2 (IC50 = 32 nM) |
| 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]. |
| 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 emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process. [1] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~680.55 mM) |
| 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. 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. 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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |