Ibuprofen Piconol
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MedKoo CAT#: 592665

CAS#: 64622-45-3

Description: Ibuprofen piconol is a Pyridyl ester of ibuprofen.


Chemical Structure

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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: 297.4
Elemental Analysis: C, 76.74; H, 7.80; N, 4.71; O, 10.76

Price and Availability

Size Price Availability Quantity
500.0mg USD 110.0 Same day
1.0g USD 190.0 Same day
2.0g USD 350.0 Same day
5.0g USD 750.0 Same day
100.0g USD 3950.0 2 weeks
500.0g USD 7450.0 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: Solid powder

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

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 168.12

Preparing Stock Solutions

The following data is based on the product molecular weight 297.4 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.

Recalculate based on batch purity %
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: 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.
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.

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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.