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    Ibuprofen (Advil; Motrin; Brufen)
    Ibuprofen (Advil; Motrin; Brufen)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1040
    CAS #: 15687-27-1 Purity ≥98%

    Description: Ibuprofen (also known as Dolgesic; Advil, Motrin, Nurofen, Brufen) is a potent anti-inflammatory drug of the NSAID class targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively. Ibuprofen, from isobutylphenylpropanoic acid, is a nonsteroidal anti-inflammatory drug (NSAID) used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. In HCT-116 p53wt or HCT-116 p53-/-colon carcinoma cell lines, S- and R-ibuprofen induced apoptosis and blocked cell cycle is in part dependent on p53. The anti-proliferative effects were significantly higher in the p53wt cell line than in the p53-deficient cells.

    References: J Nat Prod. 1998 Jan;61(1):2-7; Arteriosclerosis. 1983 Jul-Aug;3(4):383-8.

    Related CAS#: 57469-77-9 (lysine); 57469-82-6 (ariginine); 51146-56-6 (Dexibuprofen, also known as S-ibuoprofen free acid); 1113403-10-4 (Dexibuprofen lysine); 141505-32-0 (Dexibuprofen lysine hydrate); 64622-41-9 (Ibuprofen diethylaminoethyl ester); 64622-45-3 (Ibuprofen piconol); 51146-57-7 (R-Ibuprofen); 121839-78-9 ((-)-Ibuprofenamide); 121662-14-4 (Ibuprofen D3); 51146-55-5 (2-Hydroxy Ibuprofen); 1329643-44-8 [(S)-(+)-Ibuprofen D3]; 15935-54-3 (Ibuprofen carboxylic acid); 

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    Molecular Weight (MW)206.28
    FormulaC13H18O2
    CAS No.15687-27-1
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 41 mg/mL (198.8 mM)
    Water: <1 mg/mL
    Ethanol: 41 mg/mL (198.8 mM)
    Solubility (In vivo)1% DMSO+30% polyethylene glycol+1% Tween 80: 20 mg/mL 
    Other infoSynonym: Ibuprofen, Advil, Motrin, Nurofen, Brufen
    IUPAC/Chemical Name: 2-[4-(2-methylpropyl)phenyl]propanoic acid
    InChi Key: HEFNNWSXXWATRW-UHFFFAOYSA-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)
    SMILES Code: CC(C1=CC=C(CC(C)C)C=C1)C(O)=O


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    In Vitro

    In vitro activity: Ibuprofen works by inhibiting the enzyme cyclooxygenase COX-1 and COX-2, which convert arachidonic acid to prostaglandin H2 (PGH2). Its action is similar to aspirin, indomethacin and all other NSAIDs in intact cells, broken cells, and purified enzyme preparations. Ibuprofen inhibits the constitutive activation of NF-κB and IKKα in the androgen-independent prostate tumor cells PC-3 and DU-145. It sensitizes prostate cells to ionizing radiation and blocks stimulated activation of NF-κB following exposure to TNFα or ionizing radiation in the androgen-sensitive prostate tumor cell line LNCaP. Both of these cannot be attributed directly to inhibition of IκB-α kinase but to inhibition of an upstream regulator of IKKα. Ibuprofen exerts an anticancer effect by reducing survival of cancer cells. Ibuprofen is more efficacious than aspirin and acetaminophen, and comparable with (R)-flurbiprofen and indomethacin in induction of p75NTR protein (a tumor and metastasis suppressor) expression in cell lines from bladder and other organs.


    Kinase Assay: 10 μL of purified COX-1 (0.7-0.8 μg) or COX-2 (3.0 units, 0.3μg) is activated with 50 μL of cofactor solution [l-epinephrine (1.3 mg/mL), reduced glutathione (0.3 mg/mL), and hematin (1.3 mg/mL) in oxygen-free Tris-HCl buffer (pH 8.0)]. The enzyme solution (60 μL) is added to Ibuprofen solutions or DMSO (20 μL) after [14C]arachidonic acid is added in 0.2 mL eight-strip test tubes and preincubated 10 minutes on ice. Samples are incubated for 15 minutes at 37 °C, after which the reaction is terminated by addition of 10 μL of 2 M HCl and 5 μL of carrier solution (PGE2 and PGF2α, 0.2 μg/mL of each in EtOH). The unmetabolized arachidonic acid is separated from the prostaglandin products by column chromatography and eluted with n-hexane-dioxane-glacial acetic acid (70:30:1). The prostaglandin products are then eluted with EtOAc-MeOH (85:15), and the samples are counted in a Packard scintillation spectrometer. IC50 values are obtained by linear regression analysis.  


    Cell Assay: Each cell line (Bladder epithelial cell line T24, RT-4 transitional cell papilloma bladder cell line, 5637 primary carcinoma bladder cell line, HCT-116, MDAMB231, MCF7, HEK293, A549, SKOV3 and DU145) is incubated with Ibuprofen of various concentrations for 48 hours. Cell survival is estimated by the MTT assay, and cell death is determined by Hoechst staining used to distinguish between intact cell nuclei and fragmented nuclei undergoing cell death. Cells are lysed and analyzed by western blotting for detection of the p75NTR protein.

    In VivoIbuprofen reacts with the heme group of cyclooxygenase to prevent arachidonic acid conversion. Prior exposure to Ibuprofen in vivo protects cyclooxygenase completely from the irreversible effects of aspirin in platelets. Ibuprofen treatment is effective in attenuating joint inflammation and early articular cartilage degeneration in the adult female Sprague-Dawley rat model induced by high-repetition and high-force (HRHF) task. It dose this by blocking the increases in serum C1 and 2C (a biomarker of collagen I and II degradation) as well as the ratio of collagen degradation to synthesis (C1, 2C/CPII, the latter a biomarker of collage type II synthesis) induced by HRHF.
    Animal modelFemale Sprague-Dawley rats with joint inflammation induced by high-repetition and high-force (HRHF) tasks
    Formulation & DosageDissolved in DMSO and diluted in saline; 45 mg/kg; oral gavage 
    References

    J Nat Prod. 1998 Jan;61(1):2-7; Arteriosclerosis. 1983 Jul-Aug;3(4):383-8.J Biomed Biotechnol. 2011;2011:691412.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Ibuprofen

    J Biomed Biotechnol. 2011;2011:691412.
     

    Ibuprofen

    J Biomed Biotechnol. 2011;2011:691412.


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