#chirality – Page 4 – Chiralpedia

Esomeprazole

Leave a Comment / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW

Esomeprazole is used to treat conditions where there is too much acid in the stomach. It is used to treat duodenal and gastric ulcers, erosive esophagitis, gastroesophageal reflux disease (GERD), and Zollinger-Ellison syndrome, a condition wherein the stomach produces too much acid. It was launched by AstraZeneca, in 2000. Esomeprazole magnesium [AstraZeneca; http://www.astrazeneca.com] (gastrointestinal). Chirality and biological activity Esomeprazole is the (S)-(−)-enantiomer of (±)-omeprazole. It is a chiral switch (Read more about chiral switch @ my page …

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Ethambutol

Leave a Comment / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW, #drug_toxicity

(S,S)-(+)-Ethambutol is powerful and selective antitubercular drug. It is a classical example of an old drug that was introduced for clinical use in its chirally pure form. Chirality and biological activity Ethambutol contains two constitutionally symmetrical stereogenic centers in its structure and exists in three stereoisomeric forms. An enantiomeric pair (S,S)- and (R,R)-ethambutol, along with the achiral stereoisomer called meso-form. The activity of the drug resides in the (S,S)-(+)-enantiomer which is 500 and 12 fold more …

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Levofloxacin

Leave a Comment / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW

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 …

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Ascorbic acid

1 Comment / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW

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 …

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Quinine

Leave a Comment / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW

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 …

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Morphine

4 Comments / Chirality / By Valliappan Kannappan / #chiral_drugs, #chirality, #chiralpedia, #cMOTW

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 …

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D-/L- system naming: the (left-) or (right-) hand side?

5 Comments / Chirality / By Valliappan Kannappan / #chirality, #DL_system, #fischer_convention, #naming_system

The Fischer convention was introduced to specify the configuration of a stereogenic center and uses the symbols D and L. The use of capital letters is to differentiate from the “d” / “l” notation (optical descriptor) described earlier. This nomenclature system has become obsolete. In general the D/L system of nomenclature is superseded by the Cahn-Ingold-Prelog (CIP) rule to describe the configuration of a stereogenic/chiral center. But D-/L-system of naming is still employed to designate the configuration of amino acids …

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Fischer Projection: hassle free way to depict a stereoformula in 2D projection

2 Comments / Chirality / By Valliappan Kannappan / #chirality, #chiralpedia, #fischer_projection, #naming_system

One of the major problems in organic chemistry is the representation of three-dimensional structures in a two-dimensional media (viz. sheet of paper, blackboard, etc.). Chemists sometimes represent structures for chiral molecules with two-dimensional formulas called Fischer projection formulas. These two-dimensional formulas are a quick way to show three dimensions without the hassle of having to draw 3-D. The Fischer projection, devised by the carbohydrate chemist Emil Fischer in 1891. This projection formula is a technique …

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Thalidomide tragedy: the story and lessons …

2 Comments / Chirality / By Valliappan Kannappan / #chiral_drug, #chirality, #toxicity

In the 1940s and early 1950s, pregnant women throughout the world who experienced morning sickness and other anxieties associated with the first term of pregnancy were given barbiturate sedatives for relief. The issue with these barbiturates, like most sedatives, was the fact that they were highly toxic in large doses. In 1957, Chemie Grunenthal of Germany launched thalidomide as a safer alternative to barbiturate sedatives. Thalidomide, as a new sedative, was a very “attractive” drug …

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Separating mirrored molecules

2 Comments / Chiral separation and analysis / By Valliappan Kannappan / #chiral_chromatography, #chiral_membranes, #chiral_separation, #chiral_sieves, #chirality, #mirrored_molecules

In nature, most chiral molecules only appear in one specific enantiomeric form. [Read more @ the blog – “The handed world“, https://chiralpedia.com/blog/the-handed-world/]. Moreover, the handedness of the enantiomer can have a powerful effect on how that molecule behaves. The chiral difference between two molecules often plays a huge role in pharmacology and physiology, even though the two seem nearly identical but are not really in a bioenvironment, which is chiral. [Read more @ the blog …

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