| Size | Price | Stock | Qty |
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| 100mg |
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| 500mg |
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| 1g |
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| Targets |
The (R)-enantiomer of ibuprofen does not significantly inhibit cyclooxygenase (COX) enzymes. Instead, its mechanism of action is thought to involve the inhibition of NF-κB activation. NF-κB is a transcription factor that plays a central role in the inflammatory response by regulating the expression of pro-inflammatory genes. By inhibiting NF-κB activation, l-ibuprofen may exert anti-inflammatory effects through a pathway that is distinct from the COX inhibition of its (S)-enantiomer.
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| ln Vitro |
(R)-(-)-Ibuprofen is Ibuprofen's R enantiomer, which has no effect on COX but is engaged in lipid metabolic pathways and is incorporated into triglycerides alongside endogenous fatty acids[1]. At a concentration of 1 μM, (R)-(-)-ibuprofen greatly lowers NF-κB activation and totally stops induction at 10 μM. (R)-(-)-ibuprofen suppresses NF-κB luciferase activity with an IC50 of 121.8 μM, which is weaker than that of S(+)-ibuprofen (IC50, 61.7 μM). In addition, (R)-(-)-Ibuprofen (10 mM) has no effect on HSF [2].
In vitro, l-ibuprofen is inactive against cyclooxygenase (COX) enzymes. This is in contrast to the (S)-enantiomer, which is a potent COX inhibitor. However, l-ibuprofen has been shown to inhibit NF-κB activation. This activity is likely responsible for its anti-inflammatory effects. The compound's inability to inhibit COX makes it an interesting tool for studying the non-COX-mediated pathways of inflammation. |
| ln Vivo |
In vivo, l-ibuprofen has been shown to have anti-inflammatory effects. It is being studied for its potential in relieving pain. The (R)-enantiomer can be converted to the active (S)-enantiomer in the body through a process called chiral inversion, which is a significant metabolic pathway for ibuprofen. Therefore, the in vivo activity of l-ibuprofen may be partially due to its conversion to the active (S)-form.
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| Enzyme Assay |
Non-cell-based assays for l-ibuprofen typically involve measuring its ability to inhibit COX enzymes using purified COX-1 and COX-2. However, as l-ibuprofen is inactive against COX, these assays would show no significant inhibition. To study its NF-κB inhibitory activity, a cell-free assay could be used, such as an electrophoretic mobility shift assay (EMSA) to measure NF-κB DNA binding.
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| Cell Assay |
Cellular assays for l-ibuprofen are performed to study its anti-inflammatory effects. Cells, such as macrophages, are stimulated with LPS to induce inflammation. The cells are treated with l-ibuprofen, and the activation of NF-κB is measured by Western blotting or immunofluorescence. The production of pro-inflammatory cytokines is measured by ELISA. These assays confirm the compound's ability to inhibit the inflammatory response.
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| Animal Protocol |
In vivo animal models for l-ibuprofen would typically involve standard models of inflammation, such as the carrageenan-induced paw edema model in rats. The compound would be administered, and the reduction in paw swelling would be measured. However, due to chiral inversion, the observed effects would be a combination of the direct activity of l-ibuprofen and its conversion to the active (S)-enantiomer.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Known human metabolites of R-ibuprofen include R,S-3-hydroxyibuprofen, (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(2R)-2-[4-(2-methylpropyl)phenyl]propionyl]oxaoxane-2-carboxylic acid, and R-2-hydroxyibuprofen. The pharmacokinetics of l-ibuprofen are complex due to the phenomenon of chiral inversion. In vivo, a significant portion of the (R)-enantiomer is converted to the (S)-enantiomer. Therefore, the overall pharmacokinetic profile of l-ibuprofen is influenced by this metabolic conversion. It is soluble in organic solvents. Detailed PK parameters are not extensively detailed in the provided search results. |
| Toxicity/Toxicokinetics |
l-Ibuprofen has a low acute toxicity profile. Patients have survived after single doses as high as 54 g of racemic ibuprofen. However, as a research compound, its safety profile for non-clinical use is not extensively detailed. The compound is intended for research use only and is not for human consumption.
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| References | |
| Additional Infomation |
Levo-ibuprofen is a derivative of ibuprofen and is the enantiomer of devo ibuprofen.
l-Ibuprofen is the (R)-enantiomer of ibuprofen. It is also known as (R)-(-)-Ibuprofen or levibuprofen. In contrast to the (S)-enantiomer, it is inactive against COX but can inhibit NF-κB activation. It has anti-inflammatory effects and is being studied for pain relief. It has the CAS number 51146-57-7 and is supplied for research purposes. |
| Molecular Formula |
C13H18O2
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|---|---|
| Molecular Weight |
206.28
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| Exact Mass |
206.13
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| CAS # |
51146-57-7
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| PubChem CID |
114864
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
319.6±11.0 °C at 760 mmHg
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| Melting Point |
41-42ºC
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| Flash Point |
216.7±14.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.519
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| LogP |
3.72
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
203
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
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| InChi Key |
HEFNNWSXXWATRW-SNVBAGLBSA-N
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| InChi Code |
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1
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| Chemical Name |
(2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid
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| Synonyms |
(R)-(-)-Ibuprofen; Levibuprofen; l-Ibuprofen
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 4.8478 mL | 24.2389 mL | 48.4778 mL | |
| 5 mM | 0.9696 mL | 4.8478 mL | 9.6956 mL | |
| 10 mM | 0.4848 mL | 2.4239 mL | 4.8478 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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