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MedKoo Cat#: 329668 | Name: Dexibuprofen
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Description:

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

Dexibuprofen, also known as (S)-(+)-Ibuprofen, is a non-steroidal anti-inflammatory drug. It is the active dextrorotatory enantiomer of ibuprofen. Most ibuprofen formulations contain a racemic mixture of both isomers. Dexibuprofen acts as cyclooxygenase inhibitor.

Chemical Structure

Dexibuprofen
Dexibuprofen
CAS#51146-56-6 (S-)

Theoretical Analysis

MedKoo Cat#: 329668

Name: Dexibuprofen

CAS#: 51146-56-6 (S-)

Chemical Formula: C13H18O2

Exact Mass: 206.1307

Molecular Weight: 206.29

Elemental Analysis: C, 75.69; H, 8.80; O, 15.51

Price and Availability

Size Price Availability Quantity
1g USD 150.00 2 weeks
5g USD 400.00 2 weeks
10g USD 650.00 2 weeks
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Related CAS #
51146-56-6 (S-) 51146-57-7 (R-) 1113403-10-4 (S- lysine) 141505-32-0 (S- lysine hydrate)
Synonym
Dexibuprofen; Doctrin; L 669455; L-669,455, MK 233; MK-233; Dexibuprofen (free acid), (S)-(+)-Ibuprofen
IUPAC/Chemical Name
(S)-(+)-2-(4-Isobutylphenyl)propionic Acid
InChi Key
HEFNNWSXXWATRW-JTQLQIEISA-N
InChi Code
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1
SMILES Code
C[C@@H](C1=CC=C(CC(C)C)C=C1)C(O)=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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(S)-(+)-Ibuprofen ((S)-Ibuprofen), a S(+)-enantiomer of Ibuprofen, is a potent COX-1 and COX-2 inhibitor with IC50s of 2.1 μM and 1.6 μM, respectively.
In vitro activity:
TBD
In vivo activity:
It is widely demonstrated that APP/PS1 mice develop time-dependent accumulation of Aβ plaques in the brain, which is enhanced with the obesogenic diet intake. As expected, two-way ANOVA showed a significant effect of the diet (p < 0.0001) in the quantification of cortical Aβ plaques deposition in APP/PS1 mice, demonstrating an increase of these plaques caused by HFD intake. Moreover, treatment factor also results in a significant effect (p < 0.0001), indicating that long-term administration of DXI (dexibuprofen) reduced Aβ plaques deposition independent of the diet (Fig. 5A). Reference: Cell Biosci. 2021; 11: 141. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8296685/
Solvent mg/mL mM
Solubility
DMSO 56.9 275.72
DMF 30.0 145.43
Ethanol 50.0 242.38
PBS (pH 7.2) 1.0 4.85
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 206.29 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. Ettcheto M, Sánchez-Lopez E, Cano A, Carrasco M, Herrera K, Manzine PR, Espinosa-Jimenez T, Busquets O, Verdaguer E, Olloquequi J, Auladell C, Folch J, Camins A. Dexibuprofen ameliorates peripheral and central risk factors associated with Alzheimer's disease in metabolically stressed APPswe/PS1dE9 mice. Cell Biosci. 2021 Jul 22;11(1):141. doi: 10.1186/s13578-021-00646-w. PMID: 34294142; PMCID: PMC8296685. 2. Ettcheto M, Sánchez-López E, Pons L, Busquets O, Olloquequi J, Beas-Zarate C, Pallas M, García ML, Auladell C, Folch J, Camins A. Dexibuprofen prevents neurodegeneration and cognitive decline in APPswe/PS1dE9 through multiple signaling pathways. Redox Biol. 2017 Oct;13:345-352. doi: 10.1016/j.redox.2017.06.003. Epub 2017 Jun 15. PMID: 28646794; PMCID: PMC5480981.
In vitro protocol:
TBD
In vivo protocol:
1. Ettcheto M, Sánchez-Lopez E, Cano A, Carrasco M, Herrera K, Manzine PR, Espinosa-Jimenez T, Busquets O, Verdaguer E, Olloquequi J, Auladell C, Folch J, Camins A. Dexibuprofen ameliorates peripheral and central risk factors associated with Alzheimer's disease in metabolically stressed APPswe/PS1dE9 mice. Cell Biosci. 2021 Jul 22;11(1):141. doi: 10.1186/s13578-021-00646-w. PMID: 34294142; PMCID: PMC8296685. 2. Ettcheto M, Sánchez-López E, Pons L, Busquets O, Olloquequi J, Beas-Zarate C, Pallas M, García ML, Auladell C, Folch J, Camins A. Dexibuprofen prevents neurodegeneration and cognitive decline in APPswe/PS1dE9 through multiple signaling pathways. Redox Biol. 2017 Oct;13:345-352. doi: 10.1016/j.redox.2017.06.003. Epub 2017 Jun 15. PMID: 28646794; PMCID: PMC5480981.
1: Gao Z, Cui F, Cao X, Wang D, Li X, Li T. Local infiltration of the surgical wounds with levobupivacaine, dexibuprofen, and norepinephrine to reduce postoperative pain: A randomized, vehicle-controlled, and preclinical study. Biomed Pharmacother. 2017 May 29;92:459-467. doi: 10.1016/j.biopha.2017.05.038. [Epub ahead of print] PubMed PMID: 28570980. 2: Arshad N, Zafran M, Ashraf Z, Perveen F. Synthesis, characterization of amide substituted dexibuprofen derivatives and their spectral, voltammetric and docking investigations for DNA binding interactions. J Photochem Photobiol B. 2017 Apr;169:134-147. doi: 10.1016/j.jphotobiol.2017.02.021. Epub 2017 Mar 3. PubMed PMID: 28319868. 3: Ashraf Z, Alamgeer, Rasool R, Hassan M, Ahsan H, Afzal S, Afzal K, Cho H, Kim SJ. Synthesis, Bioevaluation and Molecular Dynamic Simulation Studies of Dexibuprofen-Antioxidant Mutual Prodrugs. Int J Mol Sci. 2016 Dec 21;17(12). pii: E2151. doi: 10.3390/ijms17122151. PubMed PMID: 28009827; PubMed Central PMCID: PMC5187951. 4: Sánchez-López E, Ettcheto M, Egea MA, Espina M, Calpena AC, Folch J, Camins A, García ML. New potential strategies for Alzheimer's disease prevention: pegylated biodegradable dexibuprofen nanospheres administration to APPswe/PS1dE9. Nanomedicine. 2017 Apr;13(3):1171-1182. doi: 10.1016/j.nano.2016.12.003. Epub 2016 Dec 14. PubMed PMID: 27986603. 5: Sánchez-López E, Egea MA, Cano A, Espina M, Calpena AC, Ettcheto M, Camins A, Souto EB, Silva AM, García ML. PEGylated PLGA nanospheres optimized by design of experiments for ocular administration of dexibuprofen-in vitro, ex vivo and in vivo characterization. Colloids Surf B Biointerfaces. 2016 Sep 1;145:241-50. doi: 10.1016/j.colsurfb.2016.04.054. Epub 2016 May 3. PubMed PMID: 27187188. 6: Akhlaq M, Arshad MS, Mudassir AM, Hussain A, Kucuk I, Haj-Ahmad R, Rasekh M, Ahmad Z. Formulation and evaluation of anti-rheumatic dexibuprofen transdermal patches: a quality-by-design approach. J Drug Target. 2016 Aug;24(7):603-12. doi: 10.3109/1061186X.2015.1116538. Epub 2015 Dec 17. PubMed PMID: 26586147. 7: Li Y, Zhou Y, Jiang J, Wang X, Fu Y, Gong T, Sun X, Zhang Z. Mechanism of brain targeting by dexibuprofen prodrugs modified with ethanolamine-related structures. J Cereb Blood Flow Metab. 2015 Dec;35(12):1985-94. doi: 10.1038/jcbfm.2015.160. Epub 2015 Jul 8. PubMed PMID: 26154870; PubMed Central PMCID: PMC4671119. 8: El-Houssieny BM, El-Dein EZ, El-Messiry HM. Enhancement of solubility of dexibuprofen applying mixed hydrotropic solubilization technique. Drug Discov Ther. 2014 Aug;8(4):178-84. PubMed PMID: 25262596. 9: Jin SG, Yousaf AM, Son MW, Jang SW, Kim DW, Kim JO, Yong CS, Kim JH, Choi HG. Mechanical properties, skin permeation and in vivo evaluations of dexibuprofen-loaded emulsion gel for topical delivery. Arch Pharm Res. 2015 Feb;38(2):216-22. doi: 10.1007/s12272-014-0367-8. Epub 2014 Mar 24. PubMed PMID: 24988989. 10: Zamani O, Böttcher E, Rieger JD, Mitterhuber J, Hawel R, Stallinger S, Eller N. Comparison of safety, efficacy and tolerability of dexibuprofen and ibuprofen in the treatment of osteoarthritis of the hip or knee. Wien Klin Wochenschr. 2014 Jun;126(11-12):368-75. doi: 10.1007/s00508-014-0544-2. Epub 2014 Apr 17. PubMed PMID: 24740137. 11: Derry S, Best J, Moore RA. Single dose oral dexibuprofen [S(+)-ibuprofen] for acute postoperative pain in adults. Cochrane Database Syst Rev. 2013 Oct 23;(10):CD007550. doi: 10.1002/14651858.CD007550.pub3. Review. PubMed PMID: 24151035. 12: Erratum: Safety and efficacy of an add-on therapy with curcumin phytosome and piperine and/or lipoic acid in subjects with a diagnosis of peripheral neuropathy treated with dexibuprofen [Erratum]. J Pain Res. 2013 Aug 26;6:641. eCollection 2013. PubMed PMID: 24009429; PubMed Central PMCID: PMC3762669. 13: Abdelbary G, Makhlouf A. Adoption of polymeric micelles to enhance the oral bioavailability of dexibuprofen: formulation, in-vitro evaluation and in-vivo pharmacokinetic study in healthy human volunteers. Pharm Dev Technol. 2014 Sep;19(6):717-27. doi: 10.3109/10837450.2013.823994. Epub 2013 Aug 13. PubMed PMID: 23937590. 14: Di Pierro F, Settembre R. Safety and efficacy of an add-on therapy with curcumin phytosome and piperine and/or lipoic acid in subjects with a diagnosis of peripheral neuropathy treated with dexibuprofen. J Pain Res. 2013 Jul 3;6:497-503. doi: 10.2147/JPR.S48432. Print 2013. Erratum in: J Pain Res. 2013;6:641. PubMed PMID: 23861596; PubMed Central PMCID: PMC3704545. 15: Kim CK, Callaway Z, Choung JT, Yu JH, Shim KS, Kwon EM, Koh YY. Dexibuprofen for fever in children with upper respiratory tract infection. Pediatr Int. 2013 Aug;55(4):443-9. doi: 10.1111/ped.12125. PubMed PMID: 23659181. 16: Muralidharan S. Pharmacokinetic-pharmacodynamic model of newly developed dexibuprofen sustained release formulations. ISRN Pharm. 2012;2012:451481. doi: 10.5402/2012/451481. Epub 2012 Dec 6. PubMed PMID: 23316393; PubMed Central PMCID: PMC3534360. 17: Awad H, Aboul-Enein HY, Lashin S. A validated enantioselective HPLC assay of dexibuprofen in dexibuprofen tablet formulations. Biomed Chromatogr. 2012 Apr;26(4):502-6. PubMed PMID: 22493788. 18: Zhang X, Liu X, Gong T, Sun X, Zhang ZR. In vitro and in vivo investigation of dexibuprofen derivatives for CNS delivery. Acta Pharmacol Sin. 2012 Feb;33(2):279-88. doi: 10.1038/aps.2011.144. PubMed PMID: 22301864; PubMed Central PMCID: PMC4010340. 19: Noh YH, Lim HS, Cho SH, Ghim JL, Choe S, Jung JA, Kim UJ, Park KM, Jang MJ, Bae KS. Pharmacokinetic comparison of controlled- and immediate-release formulations of dexibuprofen after single and multiple oral doses in fasting healthy male Korean volunteers. Clin Ther. 2011 Sep;33(9):1132-41. doi: 10.1016/j.clinthera.2011.07.019. Epub 2011 Aug 24. PubMed PMID: 21864907. 20: Xu MJ, Zou C, H Chu J, Wu T, Liu SJ, Zhang J, Chen M, Liu F, Xiong NN, Ju WZ, S Tan H. Pharmacokinetics and bioequivalence of single dose and multiple doses of immediate- and extended-release formulations of dexibuprofen in healthy Chinese subjects. Int J Clin Pharmacol Ther. 2011 Mar;49(3):237-46. PubMed PMID: 21329626.

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