Home Neuronal Signaling COX inhibitor Ibuprofen (NSC 256857)

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Ibuprofen (NSC 256857) COX inhibitor

Cat.No.S1638

Ibuprofen (NSC 256857, Dolgesic) is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively.
Ibuprofen (NSC 256857) COX inhibitor Chemical Structure

Chemical Structure

Molecular Weight: 206.28

Jump to Mechanism of Action Solubility Chemical Information, Storage & Stability Specificity

Quality Control

Batch: S163801 DMSO]41 mg/mL]false]Ethanol]41 mg/mL]false]Water]Insoluble]false Purity: 100%
100

Chemical Information, Storage & Stability

Molecular Weight 206.28 Formula

C13H18O2

 Storage (From the date of receipt)
CAS No. 15687-27-1 Download SDF Storage of Stock Solutions

Synonyms Dolgesic,NSC 256857 Smiles CC(C)CC1=CC=C(C=C1)C(C)C(=O)O

Solubility

In vitro
Batch:

DMSO : 41 mg/mL (198.75 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Ethanol : 41 mg/mL

Water : Insoluble

Molarity Calculator

Mass Concentration Volume Molecular Weight

In vivo
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Mechanism of Action

Features
Considered a core medicine in the WHO's "WHO Model List of Essential Medicines" (a list of the minimum medical requirements for a basic healthcare system).
Targets/IC50/Ki
COX-1 [1]
13 μM
COX-2 [1]
370 μM
In vitro
Ibuprofen (NSC 256857) 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. [1] This compound 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. [2] It 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. [3]
Kinase Assay
Radiochemical enzyme assays for COX-1 and COX-2
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)]. After [14C]arachidonic acid is added in 0.2 mL eight-strip test tubes and preincubated 10 minutes on ice, the enzyme solution (60 μL) is added to Ibuprofen (NSC 256857) solutions or DMSO (20 μL). 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.
In vivo
Ibuprofen (NSC 256857) reacts with the heme group of cyclooxygenase to prevent arachidonic acid conversion. Prior exposure to this compound in vivo protects cyclooxygenase completely from the irreversible effects of aspirin in platelets. [4] Its 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 does 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. [5]
References
  • [4] https://pubmed.ncbi.nlm.nih.gov/6411052/
  • [5] https://pubmed.ncbi.nlm.nih.gov/21403884/

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT06146491 Recruiting
Pain Postoperative
B.P. Koirala Institute of Health Sciences
 August 10 2023 Phase 4
NCT05928520 Not yet recruiting
Pain Management
Al-Azhar University
 August 1 2023 Phase 3
NCT06247462 Completed
Acute Kidney Injury
University of New Mexico
 June 1 2023 Phase 1
NCT05575700 Recruiting
Pain Acute|Hip Arthropathy|Knee Arthropathy|Safety Issues|Analgesia|Analgesic Adverse Reaction|Postoperative Pain|Postoperative Complications
Naestved Hospital
 April 17 2023 Phase 4
NCT05496868 Recruiting
Acute Respiratory Distress Syndrome Adult
Dompé Farmaceutici S.p.A
 February 7 2023 Phase 2

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