#chiralpedia

Chiral twins with independent therapeutic value Propoxyphene is a classical example of a synthetic chiral drug where the enantiomers of a chiral drug exhibit desirable but different therapeutic activity. Example of such biological behavior is exemplified by some of the natural products as well (e.g., quinine and quinidine) with anti-malarial and anti-arrhythmic activity. Chirality and biological activity Propoxyphene carries two stereogenic centers meaning it can exist in two pair of enantiomers (4 stereoisomers). One of …

Propoxyphene Read More »

The chiral switches of ‘profen’ NSAIDs Chiral switches have been successful in two non-steroidal anti-inflammatory drugs (NSAIDs) – ibuprofen and ketoprofen. The switch of ibuprofen is based on chiral inversion; (±)- and (S)-ibuprofen can be viewed as being essentially bioequivalent’. Ibuprofen carries a stereogenic center in the propanoic acid side chain and exists as a pair of enantiomers. Dexibuprofen is (S)-(+)-Ibuprofen. Chiral Inversion COX inhibition resides exclusively in the (S)-enantiomer, as shown by in vitro studies …

Dexibuprofen Read More »

Salbutamol (also known as Albuterol ) is used to prevent and treat wheezing and shortness of breath caused by breathing problems (such as asthma, chronic obstructive pulmonary disease). Salbutamol is a short-acting, selective beta2-adrenergic receptor agonist used in the treatment of asthma and Chronic obstructive pulmonary disease (COPD). Synonym Albuterol Chirality and biological activity Salbutamol is formulated as a racemic mixture of the R- and S-isomers. Bronchodilator activity resides in R-(-)-Salbutamol (eutomer); S-Salbutamol (distomer) is inactive. The …

Salbutamol Read More »

Levofloxacin is a third generation fluoroquinolone that is widely used in the treatment of mild-to-moderate respiratory and urinary tract infections due to sensitive organisms.  Levofloxacin is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as community-acquired pneumonia, acute worsening of chronic bronchitis, anthrax, urinary tract infections, acute sinus infections, and others. Chirality and biological activity Levofloxacin, the S-enantiomer of the previously marketed …

Levofloxacin Read More »

L-(+)-Ascorbic Acid is another old chiral drug from natural source. It is a water-soluble vitamin (Vitamin C). Ascorbic acid is a potent reducing and antioxidant agent that functions in fighting bacterial infections, in detoxifying reactions, and in the formation of collagen in fibrous tissue, teeth, bones, connective tissue, skin, and capillaries. Found in citrus and other fruits, and in vegetables, Vitamin C cannot be produced or stored by humans and must be obtained in the …

Ascorbic acid Read More »

Most fascinating old chiral drug, from historical point of view, is Quinine. It is known that by early 1600s quinine was being used by South American natives, in Peru, Ecuador, as a crude preparation from the bark of the Cinchona tree for the treatment of malaria. Chirality and biological activity Quinine contains two major fused ring systems: aromatic quinoline and bicyclic quiniclidine. The molecule contains four stereogenic carbon centers at C-3, C-4, C-8 and C-9, respectively …

Quinine Read More »

Many medicinal agents important to life are combinations of mirror-image twins called chiral compounds. These twins may look very similar, yet their biological makeup might differ significantly. In other words, the pharmacokinetic and pharmacodynamic profiles of the individual enantiomers that make up a racemic chiral medication might drastically vary. The Chiral Molecule of the Week #cMOTW is an effort to highlight significant chiral compounds with therapeutic value. Follow us for more …… Nature is not even …

Morphine Read More »