Dexibuprofen is a
nonsteroidal anti-inflammatory drug (NSAID).
It is the active
dextrorotatory
Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...
enantiomer of
ibuprofen.
Most ibuprofen formulations contain a
racemic mixture of both isomers.
Chemistry
Basically Dexibuprofen is a
chiral switch The word "chiral switch" was introduced by Agranat and Caner in 1999. Chiral switches are chiral drugs that are already approved as racemates but that have been re-developed as single enantiomers. The term chiral switching has been coined to descr ...
of racemic ibuprofen. The chiral carbon in dexibuprofen is assigned an absolute configuration, (S), as per Cahn-Ingold-prelog rule.
Pharmacology
Ibuprofen, is an α-arylpropionic acid, used largely in the treatment of rheumatoid arthritis and widely used over-the counter drug for headache and minor pains. This drug has a chiral center and exists as a pair of enantiomers. The (S)- ibuprofen, the
eutomer The eudysmic ratio (also spelled eudismic ratio) represents the difference in pharmacologic activity between the two enantiomers of a drug. In most cases where a chiral compound is biologically active, one enantiomer is more active than the other ...
, is responsible for the desired therapeutic effect. Interestingly, the inactive (R)-enantiomer, the
distomer The eudysmic ratio (also spelled eudismic ratio) represents the difference in pharmacologic activity between the two enantiomers of a drug. In most cases where a chiral compound is biologically active, one enantiomer is more active than the other ...
, undergoes a unidirectional chiral inversion to give the active (S)-enantiomer, the former acting as a pro-drug for the latter. That is, when the ibuprofen is administered as a racemate the distomer is converted ''in vivo'' into the eutomer while the latter is unaffected. This chiral inversion may lead to accumulation of one of the enantiomers leading to toxicity. The risk of side-effect can be avoided by the use of pure (S)-enantiomer.
See also
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Chiral switch The word "chiral switch" was introduced by Agranat and Caner in 1999. Chiral switches are chiral drugs that are already approved as racemates but that have been re-developed as single enantiomers. The term chiral switching has been coined to descr ...
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Enantiopure drug An enantiopure drug is a pharmaceutical that is available in one specific enantiomeric form. Most biological molecules (proteins, sugars, etc.) are present in only one of many chiral forms, so different enantiomers of a chiral drug molecule bind d ...
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Chirality
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Eudysmic ratio The eudysmic ratio (also spelled eudismic ratio) represents the difference in pharmacologic activity between the two enantiomers of a drug. In most cases where a chiral compound is biologically active, one enantiomer is more active than the other. ...
References
Enantiopure drugs
Nonsteroidal anti-inflammatory drugs
Propionic acids
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