Synonym
l-Ibuprofen; Levibuprofen; (R)-(-)-Ibuprofen; (R)-Ibuprofen;
IUPAC/Chemical Name
(R)-2-(4-isobutylphenyl)propanoic acid
InChi Key
HEFNNWSXXWATRW-SNVBAGLBSA-N
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
SMILES Code
O=C(O)[C@H](C)C1=CC=C(CC(C)C)C=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
(R)-(-)-Ibuprofen is the R enantiomer of Ibuprofen, inactive on COX, inhibits NF-κB activation; (R)-(-)-Ibuprofen exhibits anti-inflammatory and antinociceptive effects.
In vitro activity:
NF-kB activation was significantly reduced by treatment of Jurkat T cells with 1 mM R(7)-ibuprofen, whereas 10 mM completely prevented NF-kB induction (Figure 1a, lanes 3, 4). The NF-kB-mediated transactivation was suppressed by R(7)-ibuprofen as well as the S(+)-enantiomer in a dose-dependent manner (Figure 1b).
Reference: Br J Pharmacol. 1998 Feb;123(4):645-52. https://pubmed.ncbi.nlm.nih.gov/9517383/
In vivo activity:
Measurement of intracellular coenzyme-A levels in isolated rat hepatocytes revealed that R-ibuprofen transiently reduced coenzyme-A levels, whereas S-ibuprofen had no effect.
Reference: J Clin Pharmacol. 1996 Dec;36(12 Suppl):27S-32S. https://pubmed.ncbi.nlm.nih.gov/9013381/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
45.0 |
218.14 |
| DMSO |
63.7 |
308.63 |
| Ethanol |
50.5 |
244.81 |
| PBS (pH 7.2) |
2.0 |
9.70 |
| Water |
20.8 |
101.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
206.29
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kaehler S, Marsik C, Heinisch B, Thallinger C, Sauermann R, Kazemi-Shirazi L, Wagner O, Joukhadar C. S-ibuprofen effectively inhibits thromboxane B2 levels and platelet function in an experimental model of lipopolysaccharide-stimulated and non-stimulated whole blood. Pharmacology. 2008;81(2):181-6. doi: 10.1159/000111759. Epub 2007 Nov 28. PMID: 18043009.
2. Scheuren N, Bang H, Münster T, Brune K, Pahl A. Modulation of transcription factor NF-kappaB by enantiomers of the nonsteroidal drug ibuprofen. Br J Pharmacol. 1998 Feb;123(4):645-52. doi: 10.1038/sj.bjp.0701652. PMID: 9517383; PMCID: PMC1565210.
3. Yoshida H, Kohno Y, Endo H, Yamaguchi J, Fukushima K, Suwa T, Hayashi M. Mechanistic studies on metabolic chiral inversion of 4-(4-methylphenyl)-2-methylthiomethyl-4-oxobutanoic acid (KE-748), an active metabolite of the new anti-rheumatic agent 2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (KE-298), in rats. Biochem Pharmacol. 1997 Jan 24;53(2):179-87. doi: 10.1016/s0006-2952(96)00658-2. PMID: 9037250.
4. Mayer JM. Ibuprofen enantiomers and lipid metabolism. J Clin Pharmacol. 1996 Dec;36(12 Suppl):27S-32S. PMID: 9013381.
In vitro protocol:
1. Kaehler S, Marsik C, Heinisch B, Thallinger C, Sauermann R, Kazemi-Shirazi L, Wagner O, Joukhadar C. S-ibuprofen effectively inhibits thromboxane B2 levels and platelet function in an experimental model of lipopolysaccharide-stimulated and non-stimulated whole blood. Pharmacology. 2008;81(2):181-6. doi: 10.1159/000111759. Epub 2007 Nov 28. PMID: 18043009.
2. Scheuren N, Bang H, Münster T, Brune K, Pahl A. Modulation of transcription factor NF-kappaB by enantiomers of the nonsteroidal drug ibuprofen. Br J Pharmacol. 1998 Feb;123(4):645-52. doi: 10.1038/sj.bjp.0701652. PMID: 9517383; PMCID: PMC1565210.
In vivo protocol:
1. Yoshida H, Kohno Y, Endo H, Yamaguchi J, Fukushima K, Suwa T, Hayashi M. Mechanistic studies on metabolic chiral inversion of 4-(4-methylphenyl)-2-methylthiomethyl-4-oxobutanoic acid (KE-748), an active metabolite of the new anti-rheumatic agent 2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (KE-298), in rats. Biochem Pharmacol. 1997 Jan 24;53(2):179-87. doi: 10.1016/s0006-2952(96)00658-2. PMID: 9037250.
2. Mayer JM. Ibuprofen enantiomers and lipid metabolism. J Clin Pharmacol. 1996 Dec;36(12 Suppl):27S-32S. PMID: 9013381.
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5: Li Y, Lu J. Direct chemiluminescence determination of ibuprofen by the enhancement of the KMnO(4)-sulphite reaction. Luminescence. 2007 Jul-Aug;22(4):326-30. PubMed PMID: 17471464.
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9: Borgs M, Bollen M, Keppens S, Yap SH, Stalmans W, Vanstapel F. Modulation of basal hepatic glycogenolysis by nitric oxide. Hepatology. 1996 Jun;23(6):1564-71. PubMed PMID: 8675178.
10: Bhattacharyya DK, Lecomte M, Rieke CJ, Garavito M, Smith WL. Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H synthase-1. J Biol Chem. 1996 Jan 26;271(4):2179-84. PubMed PMID: 8567676.
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-(-)-Ibuprofen3021.jpg "(R)-(-)-Ibuprofen")
