Parecoxib sodium ( SC-69124A; Dynastat) is a novel and potent cyclooxygenase-2/COX-2 inhibitor with the potential for treating postoperative pain in adults. It is a water-soluble and injectable prodrug of valdecoxib.
Physicochemical Properties
| Molecular Formula | C19H17N2NAO4S |
| Molecular Weight | 392.4048 |
| Exact Mass | 392.08 |
| Elemental Analysis | C, 58.16; H, 4.37; N, 7.14; Na, 5.86; O, 16.31; S, 8.17 |
| CAS # | 198470-85-8 |
| Related CAS # | Parecoxib;198470-84-7;Parecoxib-d5 sodium |
| PubChem CID | 15895902 |
| Appearance | White to off-white solid powder |
| Boiling Point | 538ºC at 760mmHg |
| Melting Point | 273-275°C |
| Flash Point | 279.2ºC |
| LogP | 5.396 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 27 |
| Complexity | 581 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | S(C1C([H])=C([H])C(=C([H])C=1[H])C1=C(C([H])([H])[H])ON=C1C1C([H])=C([H])C([H])=C([H])C=1[H])([N-]C(C([H])([H])C([H])([H])[H])=O)(=O)=O.[Na+] |
| InChi Key | HQPVVKXJNZEAFW-UHFFFAOYSA-M |
| InChi Code | InChI=1S/C19H18N2O4S.Na/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)/q+1/p-1 |
| Chemical Name | sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide |
| Synonyms | SC 69124A sodium SC-69124A Parecoxib sodiumSC69124A Dynastat |
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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
| ln Vitro | In a dose-dependent manner, parecoxib sodium (0-200 μM; 24-48 hours) suppresses the growth of GBM cells [4]. Parecoxib sodium (200 μM; 24-48 hours) decreased U343 cells' ability to migrate when compared to the PBS-treated group [4]. |
| ln Vivo | In the elevated plus maze test, parecoxib sodium (ip; 2.5, 5.0, or 10 mg/kg; once daily; 21 days) had no effect on locomotor activity, but parecoxib 5 and 10 mg/kg was found to have a percentage greater level of motor activity. duration of open arms[3]. |
| Cell Assay |
Cell Viability Assay [4] Cell Types: GBM Cells: U251 and U343 Cell Tested Concentrations: 0 μM, 20 μM, 50 μM, 100 μM and 200 μM Incubation Duration: 24-48 hrs (hours) Experimental Results: Result in slower BrdU incorporation into GBM Cells include U251 and U343 cells. |
| Animal Protocol |
Animal/Disease Models: Adult male ICR mouse, 15 weeks old, weighing 25-35 grams [3] Doses: 2.5 mg/kg, 5.0 mg/kg or 10 mg/kg Route of Administration: intraperitoneal (ip) injection; 2.5, 5.0 or 10 mg /kg; one time/day; 21 days Experimental Results: Exercised anxiolytic-like effects in the elevated plus maze test. |
| References |
[1]. Effect of parecoxib, a novel intravenous cyclooxygenase type-2 inhibitor, on the postoperative opioid requirement and quality of pain control. Anesthesiology. [2]. [Selective inhibitors of cyclooxygenase-2 (COX-2), celecoxib and parecoxib: a systematic review]. Drugs Today (Barc). 2010 Feb;46 Suppl A:1-25. [3]. Chronic administration of parecoxib exerts anxiolytic-like and memory enhancing effects and modulates synaptophysin expression in mice. BMC Anesthesiol. 2017 Nov 13;17(1):152. [4]. Parecoxib inhibits glioblastoma cell proliferation, migration and invasion by upregulating miRNA-29c. Biol Open. 2017 Mar 15;6(3):311-316. |
| Additional Infomation |
Parecoxib Sodium is a water-soluble, injectable sodium salt form of parecoxib, an amide prodrug of the cyclooxygenase II (COX-2) selective, non-steroidal anti-inflammatory drug (NSAID) valdecoxib, with anti-inflammatory, analgesic, and antipyretic activities. Upon intravenous or intramuscular administration, parecoxib is hydrolyzed by hepatic carboxyesterases to its active form, valdecoxib. Valdecoxib selectively binds to and inhibits COX-2. This prevents the conversion of arachidonic acid into prostaglandins, which are involved in the regulation of pain, inflammation, and fever. This NSAID does not inhibit COX-1 at therapeutic concentrations and, therefore, does not interfere with blood coagulation. Drug Indication For the short-term treatment of postoperative pain in adults. , For the short-term treatment of postoperative pain. The decision to prescribe a selective COX-2 inhibitor should be based on an assessment of theindividual patient's overall risks (see sections 4. 3, 4. 4). |
Solubility Data
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~254.84 mM) H2O : ≥ 100 mg/mL (~254.84 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.37 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 25.0 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: ≥ 2.5 mg/mL (6.37 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 25.0 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: ≥ 2.5 mg/mL (6.37 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 100 mg/mL (254.84 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5484 mL | 12.7421 mL | 25.4842 mL | |
| 5 mM | 0.5097 mL | 2.5484 mL | 5.0968 mL | |
| 10 mM | 0.2548 mL | 1.2742 mL | 2.5484 mL |