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HomeProduct name list(R)-(-)-IBUPROFEN

(R)-(-)-IBUPROFEN

(R)-(-)-IBUPROFEN Structural

What is (R)-(-)-IBUPROFEN?

Description

Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53 μM, respectively). It is commonly synthesized as a racemic mixture of (S) and (R) isomers (Item No. item 70280). (R)-Ibuprofen is an enantiomer that is generally not considered a COX inhibitor and is instead thought to be involved in pathways of lipid metabolism as it is incorporated into triglycerides along with fatty acids. The (R) enantiomer can, however, inhibit NF-κB activation (IC50 = 121.8 μM) in response to T-cell stimulation as well as block superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 40-100 μM). 50-60% of (R)-ibuprofen is inverted to (S)-ibuprofen in humans after oral administration.

Chemical properties

White Crystalline Solid

The Uses of (R)-(-)-IBUPROFEN

A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer

The Uses of (R)-(-)-IBUPROFEN

A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer.

What are the applications of Application

(R)-Ibuprofen is an inhibitor of Cox-1 and Cox-2

Definition

ChEBI: Levibuprofen is an ibuprofen. It is an enantiomer of a dexibuprofen.

Purification Methods

Crystallise the (+) and (-) acids from EtOH or aqueous EtOH. The racemate which crystallises from pet ether with m 75-77o is sparingly soluble in H2O and has IR (film) 1705 (C=O), 2300—3700 (OH broad)cm-1. It is used as a non-steroidal anti-inflammatory. [Shiori et al. J Org Chem 43 2936 1978, Kaiser et al. J Pharm Sci 65 269 1976, J Pharm Sci 81 221 1992, Freer Acta Cryst (C) 49 1378 1993 for the (S+)-enantiomer.]

Properties of (R)-(-)-IBUPROFEN

Melting point: 41-42°C
Boiling point: 305.14°C (rough estimate)
Density  1.0176 (rough estimate)
refractive index  1.5290 (estimate)
storage temp.  Sealed in dry,2-8°C
solubility  Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
form  White crystalline powder.
pka 4.41±0.10(Predicted)
color  Colourless to Pale Beige Oil
Water Solubility  369.3mg/L(25 ºC)

Safety information for (R)-(-)-IBUPROFEN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (R)-(-)-IBUPROFEN

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