| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
No direct target as labeled internal standard. Unlabeled (S)-ibuprofen (active enantiomer) is a non-selective inhibitor of COX-1 and COX-2, involved in prostaglandin synthesis, leading to anti-inflammatory, analgesic, and antipyretic effects. (R)-ibuprofen is inactive on COX but inhibits NF-kappaB activation and exhibits anti-inflammatory and antinociceptive effects.
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|---|---|
| ln Vitro |
(R)-(-)-Ibuprofen-d3 is not biologically active as it is a deuterated internal standard. Unlabeled (R)-ibuprofen is inactive on COX but inhibits NF-kappaB activation and exhibits anti-inflammatory and antinociceptive effects. Active (S)-enantiomer inhibits COX-1 (IC50 ~2-5 uM) and COX-2 (IC50 ~10-50 uM), reducing prostaglandin synthesis.
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| ln Vivo |
Used as internal standard for quantification of ibuprofen enantiomers in PK studies and chiral analysis by MS. In vivo, unlabeled (R)-ibuprofen is partially converted to active (S)-ibuprofen by enzymatic unidirectional chiral inversion in the liver (acyl-CoA epimerase). In humans, inversion occurs at ~60%, so a significant portion of (R)-ibuprofen is converted to (S)-ibuprofen, contributing to overall anti-inflammatory activity of racemic ibuprofen.
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| Enzyme Assay |
(1) COX-1/COX-2 inhibition: incubate ovine COX-1 or human recombinant COX-2 (0.1-1 U) with arachidonic acid (10-100 uM) and (R)-ibuprofen-d3 or unlabeled ibuprofen (0.01-1000 uM) in 50 mM Tris-HCl pH8.0 at 37degC for 5-10 min. (2) Stop with 1M HCl, measure PGE2 by ELISA, calculate IC50.
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| Cell Assay |
(1) No direct cellular assays for labeled compound. For ibuprofen: seed macrophages (RAW 264.7) in 96-well plates. (2) Pre-treat with (R)-ibuprofen (0.1-1000 uM) or (S)-ibuprofen for 1 h. (3) Stimulate with LPS (1 ug/mL) for 6-24 h. (4) Collect supernatant, measure PGE2, TNF-alpha, IL-6 by ELISA. (5) For NF-kappaB: treat with (R)-ibuprofen (50-500 uM) for 1-2 h, then LPS for 30 min-2 h, perform nuclear extraction and Western blot for p65 or EMSA.
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| Animal Protocol |
(1) For chiral PK: use male SD rats (200-250 g) or Beagle dogs (8-12 kg). (2) Administer racemic ibuprofen (10-50 mg/kg) or ibuprofen-d3 by oral gavage (0.5% methylcellulose) or IV (10% DMSO/40% PEG300/5% Tween-80/45% saline). (3) Collect blood at 0,0.25,0.5,1,2,4,6,8,12,24 h. (4) Plasma deproteinized with 3 vol ice-cold acetonitrile containing (R)-(-)-Ibuprofen-d3 as IS. (5) LC-MS/MS with chiral column (Chiralpak AD-H, hexane:isopropanol:TFA 95:5:0.1), ESI- MRM m/z 205→161 (ibuprofen), m/z 208→161 (d3). (6) Quantify (R) and (S) separately, calculate PK parameters and inversion ratio.
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| ADME/Pharmacokinetics |
(R)-(-)-Ibuprofen-d3 soluble in DMSO (≥30 mg/mL), ethanol, acetonitrile. For in vivo, ibuprofen formulated in 0.5% methylcellulose for PO, or 10% DMSO/40% PEG300/5% Tween-80/45% saline for IV. For LC-MS, prepare stock in methanol or acetonitrile at 0.1-1 mg/mL. Storage: powder at -20degC for 3 years; solution at -20degC for 6 months, -80degC for 1 year.
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| Toxicity/Toxicokinetics |
Ibuprofen is safe at therapeutic doses (up to 1200 mg/day in humans; higher doses cause GI ulcers, renal impairment, cardiovascular risk). Deuterated internal standard used at trace levels (ng/mL), non-toxic. In vitro: ibuprofen 0.1-1 mM on HEK293 cells, IC50 >500 uM. In vivo: acute oral LD50 in rats ~600-800 mg/kg. (R)-enantiomer less toxic than (S). For research use only.
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| References |
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| Additional Infomation |
(R)-(-)-Ibuprofen-d3 is a deuterium-labeled stable isotope internal standard for accurate quantification of ibuprofen enantiomers in biological samples by LC-MS/MS. Ibuprofen is a chiral NSAID marketed as racemic mixture (50:50 R:S) worldwide. (S)-enantiomer is pharmacologically active, inhibiting COX-1/2 and exerting anti-inflammatory, analgesic, antipyretic effects. (R)-enantiomer is inactive on COX but undergoes unidirectional chiral inversion to active (S)-enantiomer in vivo (liver acyl-CoA epimerase), contributing to overall activity. Used to measure stereoselective disposition, chiral inversion, and interactions. Not a drug; strictly for research as analytical standard.
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| Molecular Formula |
C13H15D3O2
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|---|---|
| Molecular Weight |
209.30
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| Exact Mass |
209.149
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| CAS # |
121702-86-1
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| Related CAS # |
(R)-(-)-Ibuprofen;51146-57-7
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| PubChem CID |
59014967
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| Appearance |
White to off-white 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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| 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
|
| SMILES |
[2H]C([2H])([2H])[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
|
| InChi Key |
HEFNNWSXXWATRW-NYJKMMONSA-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/i3D3
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| Chemical Name |
(2R)-3,3,3-trideuterio-2-[4-(2-methylpropyl)phenyl]propanoic acid
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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 | 4.7778 mL | 23.8892 mL | 47.7783 mL | |
| 5 mM | 0.9556 mL | 4.7778 mL | 9.5557 mL | |
| 10 mM | 0.4778 mL | 2.3889 mL | 4.7778 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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