(R)-(-)-Ibuprofen

  • CAT Number: I003834
  • CAS Number: 51146-57-7
  • Molecular Formula: C13H18O2
  • Molecular Weight: 206.3
  • Purity: ≥95%
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<p style=/line-height:25px/>(R)-Ibuprofen, a nonsteroidal anti-inflammatory, is the less active enantiomer of ibuprofen, an inhibitor of Cox-1 and Cox-2.<br>IC50 Value: 121.8uM (inhibited the activation of NF-kB in response to T-cell stimulation) [2].<br>Target: COX1; COX2<br>S form ofibuprofen or S(+)-ibuprofen (SIB) is the biologically active isomer and is primarily responsible for the antiinflammatory activity.<br>in vitro: Cosolvents exponentially increased the solubility of both SIB and racIB, especially in the presence of PG and PEG 300. Glycerol was not very effective in increasing the aqueous solubilities of both compounds, whereas sorbitol solution had a minimal effect on their solubility. PG and PEG 300 increased the solubility of SIB by 400-fold and 1500-fold, respectively, whereas the rise in solubility for racIB was 193-fold and 700-fold, respectively, at 25 degrees C for the highest concentration of the cosolvents used (80% v/v) [1]. When (S)-(+)-IBU and (R)-(-)-IBU (1 microM) were incubated with a panel of recombinant human P450s, only CYP2C9 formed appreciable amounts of the hydroxy metabolites. At a higher IBU enantiomer concentration (500 microM), additional P450s catalyzed 2-hydroxylation (CYP3A4, CYP2C8, CYP2C19, CYP2D6, CYP2E1, and CYP2B6) and 3-hydroxylation (CYP2C19) [3].<br>in vivo: The presence of the CYP2C8*3 allele was found to influence the pharmacokinetics of (R)-ibuprofen in a gene-dose effect manner. Thus, after administration of 400 mg (R)-ibuprofen, the plasma half-life (95% confidence intervals) for individuals with genotypes CYP2C8*1/*1, CYP2C8*1/*3 and CYP2C8*3/*3, was 2.0 h (1.8-2.2), 4.2 h (1.9-6.5; P < 0.05) and 9.0 h (7.8-10.2; P < 0.002), respectively [2].<br>Clinical trial: A Study of Aleglitazar in Combination With Ibuprofen in Healthy Volunteers . Phase1<br></p>

Catalog Number I003834
CAS Number 51146-57-7
Synonyms

(-)-Ibuprofen

Molecular Formula

C13H18O2

Purity 95%
Target COX1; COX2
Solubility 10 mM in DMSO
Storage -20°C
IC50 121.8uM (inhibited the activation of NF-kB in response to T-cell stimulation) [2].
InChIKey HEFNNWSXXWATRW-SNVBAGLBSA-N
Reference

<p style=/line-height:25px/>
<br>[1]. Nerurkar J, Beach JW, Park MO, Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins. Pharm Dev Technol. 2005;10(3):413-21.
<br>[2]. Martínez C, García-Martín E, Blanco G, The effect of the cytochrome P450 CYP2C8 polymorphism on the disposition of (R)-ibuprofen enantiomer in healthy subjects. Br J Clin Pharmacol. 2005 Jan;59(1):62-9.
<br>[3]. Chang SY, Li W, Traeger SC, Confirmation that cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(-)-ibuprofen hydroxylation in vitro. Drug Metab Dispos. 2008 Dec;36(12):2513-22.
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