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Dexibuprofen
Dexibuprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is the active dextrorotatory enantiomer of ibuprofen. Most ibuprofen formulations contain a racemic mixture of both isomers. Chemistry Basically Dexibuprofen is a chiral switch 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'' i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease. The term ''non-steroidal'', common from around 1960, distinguishes these drugs from corticosteroids, which during the 1950s had acquired a bad reputation due to overuse and side-effect problems after their initial introduction in 1948. NSAIDs work by inhibiting the activity of cyclooxygenase enzymes (the COX-1 and COX-2 isoenzymes). In cells, these enzymes are involved in the synthesis of key biological mediators, namely prostaglandins, which are involved in inflammation, and thromboxanes, which are involved in blood clotting. There are two general types of NSAIDs available: non-selective, and COX-2 selective. Mo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 describe the development of single enantiomers from racemate drugs. For example, levofloxacin is a chiral switch of racemic ofloxacin. The essential principle of a chiral switch is that there is a change in the status of chirality. In general, the term chiral switch is preferred over racemic switch because the switch is usually happening from a racemic drug to the corresponding single enantiomer(s). It is important to understand that chiral switches are treated as a selection invention. A selection invention is an invention that selects a group of new members from a previously known class on the basis of superior properties. To express the pharmacological activities of each of the chiral twins of a racemic drug two technical terms have been c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 describe the development of single enantiomers from racemate drugs. For example, levofloxacin is a chiral switch of racemic ofloxacin. The essential principle of a chiral switch is that there is a change in the status of chirality. In general, the term chiral switch is preferred over racemic switch because the switch is usually happening from a racemic drug to the corresponding single enantiomer(s). It is important to understand that chiral switches are treated as a selection invention. A selection invention is an invention that selects a group of new members from a previously known class on the basis of superior properties. To express the pharmacological activities of each of the chiral twins of a racemic drug two technical terms have been c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 differently (or not at all) to target receptors. Chirality can be observed when the geometric properties of an object is not superimposable with its mirror image. Two forms of a molecule are formed (both mirror images) from a chiral carbon, these two forms are called enantiomers. One enantiomer of a drug may have a desired beneficial effect while the other may cause serious and undesired side effects, or sometimes even beneficial but entirely different effects. The desired enantiomer is known as an eutomer while the undesired enantiomer is known as the distomer. When equal amounts of both enantiomers are found in a mixture, the mixture is known as a racemic mixture. If a mixture for a drug does not have a 1:1 ratio of its enantiomers it is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enantiopure Drugs
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 differently (or not at all) to target receptors. Chirality can be observed when the geometric properties of an object is not superimposable with its mirror image. Two forms of a molecule are formed (both mirror images) from a chiral carbon, these two forms are called enantiomers. One enantiomer of a drug may have a desired beneficial effect while the other may cause serious and undesired side effects, or sometimes even beneficial but entirely different effects. The desired enantiomer is known as an eutomer while the undesired enantiomer is known as the distomer. When equal amounts of both enantiomers are found in a mixture, the mixture is known as a racemic mixture. If a mixture for a drug does not have a 1:1 ratio of its enantiomers it is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nonsteroidal Anti-inflammatory Drugs
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 use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease. The term ''non-steroidal'', common from around 1960, distinguishes these drugs from corticosteroids, which during the 1950s had acquired a bad reputation due to overuse and side-effect problems after their initial introduction in 1948. NSAIDs work by inhibiting the activity of cyclooxygenase enzymes (the COX-1 and COX-2 isoenzymes). In cells, these enzymes are involved in the synthesis of key biological mediators, namely prostaglandins, which are involved in inflammation, and thromboxanes, which are involved in blood clotting. There are two general types of NSAIDs available: non-selective, and COX-2 selective. Mos ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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. Circular birefringence and circular dichroism are the manifestations of optical activity. Optical activity occurs only in chiral materials, those lacking microscopic mirror symmetry. Unlike other sources of birefringence which alter a beam's state of polarization, optical activity can be observed in fluids. This can include gases or solutions of chiral molecules such as sugars, molecules with helical secondary structure such as some proteins, and also chiral liquid crystals. It can also be observed in chiral solids such as certain crystals with a rotation between adjacent crystal planes (such as quartz) or metamaterials. When looking at the source of light, the rotation of the plane of polarization may be either to the right (dextrorotatory ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 antipode – is one of two stereoisomers that are non-superposable onto their own mirror image. Enantiomers are much like one's right and left hands, when looking at the same face, they cannot be superposed onto each other. No amount of reorientation will allow the four unique groups on the chiral carbon (see Chirality (chemistry)) to line up exactly. The number of stereoisomers a molecule has can be determined by the number of chiral carbons it has. Stereoisomers include both enantiomers and diastereomers. Diastereomers, like enantiomers, share the same molecular formula and are non-superposable onto each other however, they are not mirror images of each other. A molecule with chirality rotates plane-polarized light. A mixture of equals am ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 arteriosus in a premature baby. It can be used by mouth or intravenously. It typically begins working within an hour. Common side effects include heartburn and a rash. Compared to other NSAIDs, it may have other side effects such as gastrointestinal bleeding. It increases the risk of heart failure, kidney failure, and liver failure. At low doses, it does not appear to increase the risk of heart attack; however, at higher doses it may. Ibuprofen can also worsen asthma. While whether it is safe in early pregnancy is unclear, it appears to be harmful in later pregnancy, so is not recommended. Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX). Ibuprofen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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. History The first known racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid. He manually separated the crystals of a mixture by hand, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt that gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from the macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an ''enantiomerically pure'' or ''enantiopure'' compound. Etymology From racemic acid found in grapes; from Latin ''racemus'' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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. The eudysmic ratio is the ratio of activity between the two. A eudysmic ratio significantly differing from 1 means that they are statistically different in activity. Eudisimic ratio (ER) reflects the degree of enantioselectivity of the biological systems. For example, (S)-propranolol (ER = 130) meaning that (S)-propranolol is 130 times more active as its (R)-enantiomer. Terminology The eutomer is the enantiomer having the desired pharmacological activity, e.g., as an active ingredient in a drug. The distomer, on the other hand, is the enantiomer of the eutomer which may have undesired bioactivity or may be bio-inert. A racemic mixture is an equal mixture of both enantiomers, which may be easier to manufacture than a single enantio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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. The eudysmic ratio is the ratio of activity between the two. A eudysmic ratio significantly differing from 1 means that they are statistically different in activity. Eudisimic ratio (ER) reflects the degree of enantioselectivity of the biological systems. For example, (S)-propranolol (ER = 130) meaning that (S)-propranolol is 130 times more active as its (R)-enantiomer. Terminology The eutomer is the enantiomer having the desired pharmacological activity, e.g., as an active ingredient in a drug. The distomer, on the other hand, is the enantiomer of the eutomer which may have undesired bioactivity or may be bio-inert. A racemic mixture is an equal mixture of both enantiomers, which may be easier to manufacture than a single enant ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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