Dexibuprofen is a
nonsteroidal anti-inflammatory drug
Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of ...
(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
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
of
ibuprofen
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arte ...
.
Most ibuprofen formulations contain a
racemic mixture
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
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, is responsible for the desired therapeutic effect. Interestingly, the inactive (R)-enantiomer, the
distomer, 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
*
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 ...
*
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 di ...
*
Chirality
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is distinguishable from ...
*
Eudysmic ratio
References
Enantiopure drugs
Nonsteroidal anti-inflammatory drugs
Propionic acids
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