Ibuprofen Piconol | CAS#64622-45-3 | Pyridyl Ester of Ibuprofen

MedKoo Cat#: 592665 | Name: Ibuprofen Piconol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ibuprofen piconol is a Pyridyl ester of ibuprofen.

Chemical Structure

Ibuprofen Piconol

CAS#64622-45-3

Theoretical Analysis

MedKoo Cat#: 592665

Name: Ibuprofen Piconol

CAS#: 64622-45-3

Chemical Formula: C19H23NO2

Exact Mass: 297.1729

Molecular Weight: 297.40

Elemental Analysis: C, 76.74; H, 7.80; N, 4.71; O, 10.76

Price and Availability

Size	Price	Availability
500mg	USD 110.00	2 weeks
1g	USD 190.00	2 weeks
2g	USD 300.00	2 weeks
5g	USD 650.00	2 weeks
10g	USD 950.00	2 Weeks

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Synonym

Ibuprofen piconol

IUPAC/Chemical Name

2-Pyridylmethyl 2-(4-isobutylphenyl)propionate

InChi Key

ACEWLPOYLGNNHV-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H23NO2/c1-14(2)12-16-7-9-17(10-8-16)15(3)19(21)22-13-18-6-4-5-11-20-18/h4-11,14-15H,12-13H2,1-3H3

SMILES Code

CC(C1=CC=C(CC(C)C)C=C1)C(OCC2=NC=CC=C2)=O

Appearance

Liquid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A9T03K05

QC Data

View QC data: current batch, Lot#A9T03K05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Ibuprofen piconol is a non-steroidal, anti-inflammatory (NSAID) agent for the topical relief of primary thermal burns and sunburns.

In vitro activity:

This study tested the effects of ibuprofen, a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that possesses protective properties for neuronal cells, on inhibitory differentiation in N1E-115 cells harboring the 292CA or Q39X mutant constructs. Treatment of these cells with ibuprofen for 2 or 3 days reversed inhibitory differentiation into phenotypes by more than 75% or more than 80%, respectively (Figure 12A,B). Similar results were obtained in cells harboring the Q39X mutant constructs (Figure 12C,D). Further, while the 292CA or Q39X mutant proteins exhibited aggregate-like structures in more than 75% of cells, treatment with ibuprofen decreased this incidence to less than 50% (Figure 13A,B). Consistently, ibuprofen diminished the presence of actin and 292CA mutant proteins in the lysosome (Figure 9D, blots 1 and 3). A similar change to decrease in localization in the lysosome was observed in the case of Q39X mutant proteins (Figure 9D, blot 1). Together, these results suggest that ibuprofen reverses the mutant-mediated phenotypes. Reference: Medicines (Basel). 2020 May; 7(5): 25. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7281511/

In vivo activity:

In order to determine the effects of ibuprofen on cancer cell metastasis and stemness in vivo, this study implanted 4T1-luciferase cells into the fourth fat pad of female Balb/c mice. Seven days after implantation, this study IP-injected the mice with 20 mg/kg ibuprofen, 40 mg/kg ibuprofen or DMSO (control group) two times per week (Fig. 2a). Results showed that tumour volume decreases in the ibuprofen-treated groups versus the control (Fig. 2b). However, the body weight did not change in the ibuprofen-treated groups versus the control (Fig. 2c). In addition, the survival time increases in the ibuprofen-treated groups versus control (Fig. 2d). With respect to the effect of ibuprofen on cancer cell metastasis, lung metastasis decreases in ibuprofen-treated groups versus the control (Fig. 2e–g). With respect to the effect of ibuprofen on cancer cell stemness properties, the immunocytochemical staining of SOX2 and OCT4 stemness markers decreases in the ibuprofen-treated groups versus DMSO controls (Fig. 2h, i). Reference: Br J Cancer. 2020 Sep 1; 123(5): 730–741. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463005/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	168.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 297.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Takeuchi Y, Tanaka M, Okura N, Fukui Y, Noguchi K, Hayashi Y, Torii T, Ooizumi H, Ohbuchi K, Mizoguchi K, Miyamoto Y, Yamauchi J. Rare Neurologic Disease-Associated Mutations of AIMP1 are Related with Inhibitory Neuronal Differentiation Which is Reversed by Ibuprofen. Medicines (Basel). 2020 May 6;7(5):25. doi: 10.3390/medicines7050025. PMID: 32384815; PMCID: PMC7281511. 2. Gao X, Guo N, Xu H, Pan T, Lei H, Yan A, Mi Y, Xu L. Ibuprofen induces ferroptosis of glioblastoma cells via downregulation of nuclear factor erythroid 2-related factor 2 signaling pathway. Anticancer Drugs. 2020 Jan;31(1):27-34. doi: 10.1097/CAD.0000000000000825. PMID: 31490283. 3. Shen W, Zhang X, Du R, Gao W, Wang J, Bao Y, Yang W, Luo N, Li J. Ibuprofen mediates histone modification to diminish cancer cell stemness properties via a COX2-dependent manner. Br J Cancer. 2020 Sep;123(5):730-741. doi: 10.1038/s41416-020-0906-7. Epub 2020 Jun 12. PMID: 32528119; PMCID: PMC7463005. 4. Peng J, Wu S, Guo C, Guo K, Zhang W, Liu R, Li J, Hu Z. Effect of Ibuprofen on Autophagy of Astrocytes During Pentylenetetrazol-Induced Epilepsy and its Significance: An Experimental Study. Neurochem Res. 2019 Nov;44(11):2566-2576. doi: 10.1007/s11064-019-02875-5. Epub 2019 Sep 18. PMID: 31535354.

In vitro protocol:

In vivo protocol:

1. Shen W, Zhang X, Du R, Gao W, Wang J, Bao Y, Yang W, Luo N, Li J. Ibuprofen mediates histone modification to diminish cancer cell stemness properties via a COX2-dependent manner. Br J Cancer. 2020 Sep;123(5):730-741. doi: 10.1038/s41416-020-0906-7. Epub 2020 Jun 12. PMID: 32528119; PMCID: PMC7463005. 2. Peng J, Wu S, Guo C, Guo K, Zhang W, Liu R, Li J, Hu Z. Effect of Ibuprofen on Autophagy of Astrocytes During Pentylenetetrazol-Induced Epilepsy and its Significance: An Experimental Study. Neurochem Res. 2019 Nov;44(11):2566-2576. doi: 10.1007/s11064-019-02875-5. Epub 2019 Sep 18. PMID: 31535354.

1: Christensen JM, Stalker D. Ibuprofen piconol hydrolysis in vitro in plasma, whole blood, and serum using different anticoagulants. J Pharm Sci. 1991 Jan;80(1):29-31. PubMed PMID: 2013845. 2: Kubo K, Shirai K, Akaeda T, Oguchi M. Contact dermatitis from ibuprofen piconol. Contact Dermatitis. 1988 Mar;18(3):188-9. PubMed PMID: 3365979. 3: Kimura T, Doi K. Spontaneous comedones on the skin of hairless descendants of Mexican hairless dogs. Exp Anim. 1996 Oct;45(4):377-84. PubMed PMID: 8902502. 4: Kaluzny BD, Bannow CA. High-performance liquid chromatographic determination of pimeprofen and its metabolite ibuprofen in sheep plasma and lymph. J Chromatogr. 1987 Feb 20;414(1):228-34. PubMed PMID: 3571388. 5: Inoue Y, Isobe M, Shiohara T, Hayashi H. Inhibitory activity of CX-659S, a novel diaminouracil derivative, against the rebound phenomenon following withdrawal of corticosteroid therapy for chronic contact hypersensitivity responses. Int Arch Allergy Immunol. 2003 Jun;131(2):143-52. PubMed PMID: 12811023.