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Chemical Compound Review

l-Ibuprofen     (2R)-2-[4-(2-methylpropyl) phenyl]propanoic...

Synonyms: SureCN29057, CHEMBL427526, AG-F-72703, CHEBI:47835, CS-1394, ...
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Disease relevance of l-Ibuprofen

  • The results indicate that the fatty liver condition stereoselectively affects (R)-ibuprofen clearance and eliminates preferential (S)-isomer hepatic distribution [1].

High impact information on l-Ibuprofen

  • Ratios of IC50 values for cyclooxygenase inhibition by D- and L-ibuprofen, a competitive cyclooxygenase inhibitor, were 32, 67, and 7.1 for native PGHS-1, R120Q PGHS-1, and Y355F PGHS-1, respectively [2].
  • The bioavailabilities of (R)-ibuprofen and total ibuprofen were 0.92 +/- 0.11 and 0.95 +/- 0.08, respectively [3].
  • Inhibition of nitric oxide synthase [NOS; 100 micromol/l N(G)-nitro-L-arginine methyl ester (L-NAME)] and cyclooxygenase (COX; 10 micromol/l ibuprofen) prevented the sustained response of the afferent arteriole but did not reduce the magnitude of the initial dilation (97 +/- 7%) [4].
  • It appeared that the extent of metabolic activation of (R)-ibuprofen to the (S)-isomer in renally compromised patients was greater than that in a normal setting [5].
  • Total (R)-ibuprofen clearance (ClRtot), chiral inversion-related clearance (ClRinv), (S)-ibuprofen clearance (ClS) and hepatic distribution coefficients for each stereoisomer (KR and KS) were calculated with a model that corrected for perfusate reservoir sampling [1].

Biological context of l-Ibuprofen

  • The presence of the CYP2C8*3 allele was found to influence the pharmacokinetics of (R)-ibuprofen in a gene-dose effect manner [6].
  • Additional simulations of S/R AUC ratios, for administration of (-)-(R)-ibuprofen only, ranged from 1.5 (presystemic bioinversion) to 0.66 (systemic bioinversion) [7].
  • The inversion of the pharmacologically inactive (-)-(R)-ibuprofen to the active (+)-(S)-ibuprofen was shown to obey apparent first-order kinetics during 5 h and to increase linearly with increasing hepatocyte concentration up to 4 x 10(5) cells/ml [8].
  • In the absence of protein binding, ibuprofen was metabolized via inversion and other pathways, whereas fenoprofen metabolism was essentially restricted to inversion of the (R)-enantiomer; fraction inverted (+/- SE) was 0.37 +/- 0.05 for (R)-ibuprofen and 0.85 +/- 0.03 for (R)-fenoprofen [9].

Anatomical context of l-Ibuprofen


Associations of l-Ibuprofen with other chemical compounds


Gene context of l-Ibuprofen

  • AIMS: To study the effect of CYP2C8*3, the most common CYP2C8 variant allele on the dis-position of (R)-ibuprofen and the association of CYP2C8*3 with variant CYP2C9 alleles [6].
  • The effect of the cytochrome P450 CYP2C8 polymorphism on the disposition of (R)-ibuprofen enantiomer in healthy subjects [6].

Analytical, diagnostic and therapeutic context of l-Ibuprofen


  1. Ibuprofen stereoisomer hepatic clearance and distribution in normal and fatty in situ perfused rat liver. Cox, J.W., Cox, S.R., VanGiessen, G., Ruwart, M.J. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
  2. Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H synthase-1. Bhattacharyya, D.K., Lecomte, M., Rieke, C.J., Garavito, M., Smith, W.L. J. Biol. Chem. (1996) [Pubmed]
  3. Lack of presystemic inversion of (R)- to (S)-ibuprofen in humans. Hall, S.D., Rudy, A.C., Knight, P.M., Brater, D.C. Clin. Pharmacol. Ther. (1993) [Pubmed]
  4. Determinants of renal microvascular response to ACh: afferent and efferent arteriolar actions of EDHF. Wang, X., Loutzenhiser, R. Am. J. Physiol. Renal Physiol. (2002) [Pubmed]
  5. Stereoselective disposition of ibuprofen in patients with renal dysfunction. Chen, C.Y., Chen, C.S. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  6. The effect of the cytochrome P450 CYP2C8 polymorphism on the disposition of (R)-ibuprofen enantiomer in healthy subjects. Martínez, C., García-Martín, E., Blanco, G., Gamito, F.J., Ladero, J.M., Agúndez, J.A. British journal of clinical pharmacology. (2005) [Pubmed]
  7. An evaluation of ibuprofen bioinversion by simulation. Romero, A.J., Rackley, R.J., Rhodes, C.T. Chirality. (1991) [Pubmed]
  8. Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes. Müller, S., Mayer, J.M., Etter, J.C., Testa, B. Chirality. (1990) [Pubmed]
  9. Pulmonary inversion of 2-arylpropionic acids: influence of protein binding. Hall, S.D., Hassanzadeh-Khayyat, M., Knadler, M.P., Mayer, P.R. Chirality. (1992) [Pubmed]
  10. Metabolic inversion of (R)-ibuprofen. Formation of ibuprofenyl-coenzyme A. Tracy, T.S., Wirthwein, D.P., Hall, S.D. Drug Metab. Dispos. (1993) [Pubmed]
  11. Clofibric acid increases the undirectional chiral inversion of ibuprofen in rat liver preparations. Roy-de Vos, M., Mayer, J.M., Etter, J.C., Testa, B. Xenobiotica (1996) [Pubmed]
  12. Inhibition of cytokine production and adhesion molecule expression by ibuprofen is without effect on transendothelial migration of monocytes. Menzel, E.J., Burtscher, H., Kolarz, G. Inflammation (1999) [Pubmed]
  13. Ibuprofen levels in serum and synovial fluid. Mäkelä, A.L., Lempiäinen, M., Ylijoki, H. Scand. J. Rheumatol. Suppl. (1981) [Pubmed]
  14. Stereoselective disposition of suspensions of conventional and wax-matrix sustained release ibuprofen microspheres in rats. Adeyeye, C.M., Chen, F.F. Pharm. Res. (1997) [Pubmed]
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