| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| 1g |
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| 2g | |||
| Other Sizes |
| Targets |
S-(+)-Ketoprofen targets cyclooxygenase-1 (COX-1) with a Ki of 1.8 μM [1]
S-(+)-Ketoprofen targets cyclooxygenase-2 (COX-2) with a Ki of 3.2 μM [1] |
|---|---|
| ln Vitro |
S-(+)-Ketoprofen (compound 1) has an IC50 of 1.9 nM for COX-1 and 27 nM for COX-2, making it a strong inhibitor of both COXs [1].
S-(+)-Ketoprofen (0.1 μM–10 μM) dose-dependently inhibited the catalytic activity of both COX-1 and COX-2 enzymes. At 10 μM, it achieved 92% inhibition of COX-1 and 85% inhibition of COX-2 [1] Computational modeling revealed that S-(+)-Ketoprofen binds to the active site of COX enzymes via hydrophobic interactions with non-polar residues and a hydrogen bond with the key residue Tyr355. The binding induced displacement of water molecules in the COX-1 active site, contributing to its slightly higher affinity for COX-1 than COX-2 [1] The selectivity index (COX-2 Ki / COX-1 Ki) of S-(+)-Ketoprofen was 1.78, indicating moderate preference for COX-1 [1] |
| Enzyme Assay |
COX-1/COX-2 inhibitory activity assay: Recombinant human COX-1 and COX-2 enzymes were separately incubated with different concentrations of S-(+)-Ketoprofen (0.1 μM–10 μM) in assay buffer at 37°C for 15 minutes. Arachidonic acid was added as the substrate to initiate the reaction, and the mixture was incubated for another 30 minutes. The amount of prostaglandin E2 (PGE2), the reaction product, was quantified by a specific immunoassay. Ki values were calculated using the Cheng-Prusoff equation based on the inhibition rates of PGE2 production [1]
Computational binding modeling assay: Three-dimensional structures of COX-1 and COX-2 active sites were constructed, and S-(+)-Ketoprofen was docked into the active sites using molecular modeling software. The binding interactions (hydrophobic contacts, hydrogen bonds) and water molecule distribution in the active sites were analyzed to evaluate binding affinity and selectivity [1] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
After oral administration, dexketoprofen has an onset of action within 30 minutes. The plasma half-life of dexketoprofen is approximately 4–6 hours. Peak plasma concentration (Cmax) is approximately 30 minutes. 70% to 80% of the ingested dose is excreted in the urine within 12 hours after ingestion, primarily as an acyl conjugate. <0.25 L/kg It is primarily cleared via glucuronidation, followed by renal excretion, mainly in its unchanged form. Metabolism/Metabolites Dexketoprofen is highly lipophilic and is metabolized in the liver via glucuronidation. In one study, after oral administration of 25 mg dexketoprofen to young, healthy adults, the time to peak concentration (Tmax) was approximately 30 minutes, and the peak plasma concentration (Cmax) was 3.7 ± 0.72 mg/L. Dexketoprofen is metabolized by hepatic cytochrome P450 enzymes (CYP2C8 and CYP2C9) to dexketoprofen tromethamine. It has multiple metabolites, with hydroxyl derivatives accounting for the majority of dexketoprofen tromethamine. Hydroxylation is relatively minor in the human body. Dexketoprofen is primarily bound to acyl glucuronide. Biological half-life 1.65 hours |
| Toxicity/Toxicokinetics |
Protein Binding
High protein binding. |
| References | |
| Additional Infomation |
Dexketoprofen is a monocarboxylic acid with the structure (S)-hydrotropinic acid, where a benzoyl group is substituted at the 3-position of the benzene ring. It is a cyclooxygenase inhibitor used to relieve short-term pain, such as muscle pain, toothache, and dysmenorrhea. It is a nonsteroidal anti-inflammatory drug (NSAID), a cyclooxygenase 1 inhibitor, a cyclooxygenase 2 inhibitor, and a non-narcotic analgesic. It is a monocarboxylic acid belonging to the benzophenone class of compounds. Its function is related to (S)-hydrotropinic acid. Dexketoprofen is a nonsteroidal anti-inflammatory drug. It is sold in several countries in Europe, Asia, and Latin America. It has analgesic, antipyretic, and anti-inflammatory effects.
Drug Indications For short-term treatment of mild to moderate pain, including dysmenorrhea, musculoskeletal pain, and toothache. In ...> For short-term treatment of mild to moderate pain, including dysmenorrhea, musculoskeletal pain, and toothache. For short-term treatment of mild to moderate pain, including dysmenorrhea, musculoskeletal pain, and toothache. For short-term treatment of mild to moderate pain, including dysmenorrhea, musculoskelet Mechanism of Action: It is a nonsteroidal anti-inflammatory drug (NSAID) that reduces prostaglandin synthesis by inhibiting the activity of the cyclooxygenase pathway (COX-1 and COX-2). Pharmacodynamics: This drug is an isomer of ketoprofen. Dexketoprofen is a propionic acid derivative with analgesic, anti-inflammatory, and antipyretic effects. S-(+)-ketoprofen is the active enantiomer of ketoprofen, a nonsteroidal anti-inflammatory drug (NSAID) [1] Its mechanism of action involves the inhibition of cyclooxygenase (COX), which is responsible for converting arachidonic acid into prostaglandins, thereby reducing inflammation, pain and fever [1] This study focuses on the structural basis of its COX inhibitory selectivity, emphasizing that the hydration state of the COX-1 and COX-2 active sites plays a key role in the enantiomer's binding preference [1] Compared to the R-(-)-enantiomer, S-(+)-ketoprofen exhibits higher COX inhibitory activity due to a more favorable binding interaction with the enzyme's active site [1] |
| Molecular Formula |
C₁₆H₁₄O₃
|
|---|---|
| Molecular Weight |
254.28
|
| Exact Mass |
254.094
|
| CAS # |
22161-81-5
|
| Related CAS # |
Ketoprofen;22071-15-4;Dexketoprofen (trometamol);156604-79-4
|
| PubChem CID |
667550
|
| Appearance |
White to off-white solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
431.3±28.0 °C at 760 mmHg
|
| Melting Point |
75-78ºC(lit.)
|
| Flash Point |
228.8±20.5 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.592
|
| LogP |
2.81
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
19
|
| Complexity |
331
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C[C@@H](C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
|
| InChi Key |
DKYWVDODHFEZIM-NSHDSACASA-N
|
| InChi Code |
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m0/s1
|
| Chemical Name |
Benzeneacetic acid, 3-benzoyl-alpha-methyl-, (S)-
|
| Synonyms |
(S)-Ketoprofen Dexketoprofen (S)-(+)-Ketoprofen
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| 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~393.27 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.18 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 (8.18 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 (8.18 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 | 3.9327 mL | 19.6634 mL | 39.3267 mL | |
| 5 mM | 0.7865 mL | 3.9327 mL | 7.8653 mL | |
| 10 mM | 0.3933 mL | 1.9663 mL | 3.9327 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.
Parecoxib vs. Dexketoprofen for the Management of Pain After Cesarean Section.
CTID: NCT04847024
Phase: N/A Status: Completed
Date: 2021-10-11
Products are for research use only; We do not sell to patients
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