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57469-77-9

57469-77-9 structure
57469-77-9 structure
  • Name: Ibuprofen Lysine
  • Chemical Name: (2S)-2,6-diaminohexanoic acid,2-[4-(2-methylpropyl)phenyl]propanoic acid
  • CAS Number: 57469-77-9
  • Molecular Formula: C19H30N2O3
  • Molecular Weight: 352.468
  • Catalog: Biochemical Amino acids and their derivatives Lysine derivative
  • Create Date: 2018-06-12 16:40:15
  • Modify Date: 2024-01-11 12:39:01
  • Ibuprofen ((±)-Ibuprofen) L-lysine is a potent orally active, selective COX-1 inhibitor with an IC50 value of 13 μM. Ibuprofen L-lysine inhibits cell proliferation, angiogenesis, and induces cell apoptosis. Ibuprofen L-lysine is a nonsteroidal anti-inflammatory agent and a nitric oxide (NO) donor. Ibuprofen L-lysine can be used in the research of pain, swelling, inflammation, infection, immunology, cancers[1][2][3][4][5][6][7][8].

Name (2S)-2,6-diaminohexanoic acid,2-[4-(2-methylpropyl)phenyl]propanoic acid
Synonyms L-Lysine, compd. with α-methyl-4-(2-methylpropyl)benzeneacetic acid (1:1)
S1518_Selleck
Ibuprofen lysine (USAN)
Ibuprofen Lysinate
2-(4-Isobutylphenyl)propanoic acid - L-lysine (1:1)
NeoProfen
Ibuprofen Lysine
EINECS 260-751-7
MFCD01716155
Neoprofen (TN)
Description Ibuprofen ((±)-Ibuprofen) L-lysine is a potent orally active, selective COX-1 inhibitor with an IC50 value of 13 μM. Ibuprofen L-lysine inhibits cell proliferation, angiogenesis, and induces cell apoptosis. Ibuprofen L-lysine is a nonsteroidal anti-inflammatory agent and a nitric oxide (NO) donor. Ibuprofen L-lysine can be used in the research of pain, swelling, inflammation, infection, immunology, cancers[1][2][3][4][5][6][7][8].
Related Catalog
Target

IC50: 13 μM (COX-1), 370 μM (COX-2)

In Vitro Ibuprofen (24 h) L-lysine inhibits COX-1 and COX-2 activity with IC50 values of 13 μM and 370 μM[1]. Ibuprofen (500 μM, 48 h) L-lysine inhibits cell proliferation and angiogenesis, and induces apoptosis in AGS cells (Adenocarcinoma gastric cell line)[2]. Ibuprofen (500 μM, 48 h) L-lysine 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 (500 μM, 24 h) L-lysine 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 (500 μM, 24 h) L-lysine 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 (300 mg/kg; p.o.; daily, for 14 days) L-lysine reduces overall tumor growth and enhances anti-tumor immune characteristics without adverse autoimmune reactions in a model of postpartum breast cancer[5]. Ibuprofen (60 mg/kg; i.h.; every second day for 15 days) L-lysine reduces the risk of neuropathy in a rat model of chronic Oxaliplatin‑induced peripheral neuropathy[6]. Ibuprofen (20 mg/kg; p.o.; every 12 hours, 5 doses total) L-lysine decreases muscle growth (average muscle fiber cross-sectional area) without affecting regulation of supraspinatus tendon adaptions to exercise[7]. Ibuprofen (35 mg/kg; p.o.; twice daily) L-lysine 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.

Boiling Point 319.6ºC at 760 mmHg
Molecular Formula C19H30N2O3
Molecular Weight 352.468
Exact Mass 352.236206
PSA 95.41000
LogP 3.91530
Storage condition -20℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OL5672000
CHEMICAL NAME :
L-Lysine, mono(alpha-methyl-4-(2-methylpropyl)benzeneacetate)
CAS REGISTRY NUMBER :
57469-77-9
LAST UPDATED :
198702
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C13-H18-O2.C6-H14-N2-O2
MOLECULAR WEIGHT :
352.53

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
841 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 14,126,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
485 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 14,126,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
299 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 14,126,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 14,126,1978