ibuprofen sodium salt

Names

[ Name ]:
ibuprofen sodium salt

[Synonym ]:
EINECS 250-477-6
Sodium ibuprofen
sodium 2-[4-(2-methylpropyl)phenyl]propanoate
p-Isobutylhydratropic acid sodium salt
2-(4'-isobutylphenyl)propionic acid,sodium salt
Sodium 2-(4-isobutylphenyl)propionate
Hydratropic acid,p-isobutyl-,sodium salt
Ibuprofen sodium salt
Ibuprofen sodium
(RS)-ibuprofen sodium
2-(p-isobutylphenyl)propionic acid sodium salt

Biological Activity

[Description]:

Ibuprofen ((±)-Ibuprofen) sodium is an orally active, selective COX-1 inhibitor with an IC50 value of 13 μM. Ibuprofen sodium inhibits cell proliferation, angiogenesis, and induces cell apoptosis. Ibuprofen sodium is a nonsteroidal anti-inflammatory agent and a nitric oxide (NO) donor. Ibuprofen sodium can be used in the research of pain, swelling, inflammation, infection, immunology, cancers[1][2][5][8].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

Research Areas >> Neurological Disease

[Target]

COX-1:13 μM (IC50)

COX-2:370 μM (IC50)

[In Vitro]

Ibuprofen sodium (24 h) inhibits COX-1 and COX-2 activity with IC50 values of 13 μM and 370 μM[1]. Ibuprofen sodium (500 μM, 48 h) inhibits cell proliferation and angiogenesis, and induces apoptosis in AGS cells (Adenocarcinoma gastric cell line)[2]. Ibuprofen sodium (500 μM, 48 h) downregulates transcription of Akt, VEGF-A, PCNA, Bcl2, OCT3/4 and CD44 genes, but upregulates RNA levels of wild type P53 and Bax genes in AGS cell[2]. Ibuprofen sodium (500 μM, 24 h) restores microtubule reformation, microtubule-dependent intracellular cholesterol transport, and induces extension of microtubules to the cell periphery in both cystic fibrosis (CF) cell models and primary CF nasal epithelial cells[3]. Ibuprofen sodium (500 μM, 24 h) enhances UV-induced cell death in MCF-7 cells and MDA-MB-231 cells by a photosensitization process[4]. Cell Viability Assay[2] Cell Line: AGS cells Concentration: 100-1000 μM Incubation Time: 24 h, 48 h Result: Inhibited AGS cell viability with IC50 values of 630 μM (trypan blue staining, 24 h), 456 μM (neutral red assay, 24 h), 549 μM (trypan blue staining , 48 h) and 408 μM (neutral red assay, 48 h).

[In Vivo]

Ibuprofen sodium (fed in animal feedings, 300 mg/kg, 14 days) reduces overall tumor growth and enhances anti-tumor immune characteristics without adverse autoimmune reactions in a model of postpartum breast cancer[5]. Ibuprofen sodium (subcutaneous injection, 60 mg/kg, every second day for 15 days) reduces the risk of neuropathy in a rat model of chronic Oxaliplatin‑induced peripheral neuropathy[6]. Ibuprofen sodium (oral administration, 20 mg/kg, every 12 hours, 5 doses total) decreases muscle growth (average muscle fiber cross-sectional area) without affecting regulation of supraspinatus tendon adaptions to exercise[7]. Ibuprofen sodium (oral administration, 35 mg/kg, twice daily) attenuates the Inflammatory response to pseudomonas aeruginosa in a rat model of chronic pulmonary infection[8]. Animal Model: Syngeneic (D2A1) orthotopic Balb/c mouse model of PPBC (postpartum)[5] Dosage: 300 mg/kg, daily for 14 days Administration: Fed in animal feedings (added to pulverized standard chow and mixed dry, then mixed with water, made into chow pellets and dried thoroughly) Result: Suppresed tumor growth, reduced presence of immature monocytes and increased numbers of T cells. Enhanced Th1 associated cytokines as well as promoted tumor border accumulation of T cells. Animal Model: Oxaliplatin‑induced peripheral neuropathy[6] Dosage: 60 mg/kg, every second day for 15 days Administration: Subcutaneous injection Result: Lowered sensory nerve conduction velocity (SNCV).

[References]

[1]. Noreen Y, et al. Development of a radiochemical cyclooxygenase-1 and -2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis. J Nat Prod. 1998 Jan;61(1):2-7.

[2]. Hassan Akrami, et al. Inhibitory effect of ibuprofen on tumor survival and angiogenesis in gastric cancer cell. Tumour Biol. 2015 May;36(5):3237-43.

[3]. Sharon M Rymut, et al. Ibuprofen regulation of microtubule dynamics in cystic fibrosis epithelial cells. Am J Physiol Lung Cell Mol Physiol. 2016 Aug 1;311(2):L317-27.

[4]. Emmanuelle Bignon, et al. Ibuprofen and ketoprofen potentiate UVA-induced cell death by a photosensitization process. Sci Rep. 2017 Aug 21;7(1):8885.

[5]. Nathan D Pennock, et al. Ibuprofen supports macrophage differentiation, T cell recruitment, and tumor suppression in a model of postpartum breast cancer. J Immunother Cancer. 2018 Oct 1;6(1):98.

[6]. Thomas Krøigård, et al. Protective effect of ibuprofen in a rat model of chronic oxaliplatin-induced peripheral neuropathy. Exp Brain Res. 2019 Oct;237(10):2645-2651.

[7]. Sarah Ilkhanipour Rooney, et al. Ibuprofen Differentially Affects Supraspinatus Muscle and Tendon Adaptations to Exercise in a Rat Model. Am J Sports Med. 2016 Sep;44(9):2237-45.

[8]. M W Konstan, et al. Ibuprofen attenuates the inflammatory response to Pseudomonas aeruginosa in a rat model of chronic pulmonary infection. Implications for antiinflammatory therapy in cystic fibrosis. Am Rev Respir Dis. 1990 Jan;141(1):186-92.

Chemical & Physical Properties

[ Density]:
1.029g/cm3

[ Boiling Point ]:
319.6ºC at 760 mmHg

[ Melting Point ]:
75-77ºC

[ Molecular Formula ]:
C₁₃H₁₇NaO₂

[ Molecular Weight ]:
228.26300

[ Flash Point ]:
216.7ºC

[ Exact Mass ]:
228.11300

[ PSA ]:
40.13000

[ LogP ]:
1.73850

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents

[ Water Solubility ]:
H2O: 100 mg/mL, may be clear to slightly hazy

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MU6641000

CHEMICAL NAME :: Hydratropic acid, p-isobutyl-, sodium salt

CAS REGISTRY NUMBER :: 31121-93-4

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C13-H17-O2.Na

MOLECULAR WEIGHT :: 228.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 38,238,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
MU6641000

[ HS Code ]:
2916399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916399090

[ Summary ]:
2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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