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11. Read the article below about the Chiral Drugs Carefully: medically speaking Chiral Drugs Thousands of drugs are marketed throughout the world. The origins of these drugs fall into three categories: Ibuprofen is an analgesic (painkiller) with anti-inflammatory properties. The S enantiomer is the active agent, while the R enantiomer is inactive. Nevertheless, ibuprofen is sold as a mixture of both enantiomers (under the trade names Advil and Motrin), because the benefit of separating the enantiomers is not clear. In fact, there is evidence that the human body is capable of slowly converting the R enantiomer into the desired S enantiomer. Many synthetic drugs are sold as a mixture of enantiomers, because of the high cost and difficulty associated with separating enantiomers. In many cases, enantiomers can trigger entirely different physiological responses. For example, consider the enantiomers of Timolol: 1. natural products-compounds isolated from natural sources, such as plants or bacteria, 2. natural products that have been chemically modified in the laboratory, or 3. synthetic compounds (made entirely in the laboratory). Most drugs obtained from natural sources consist of a single enantiomer. It is important to realize that a pair of enantiomers will rarely exhibit the same potency. We have seen in previous chapters that drug action is usually the result of drug-receptor binding. If the drug binds to the receptor in at least three places (called three-point binding), then one enantiomer of the drug may be more capable of binding with the receptor: OH OH (S)-Timolol (R)-Timolol CO CO2 H The S enantiomer treats angina and high blood pressure, while the R enantiomer is useful in treating glaucoma. In this +NH, +NH

11. Read the article below about the Chiral Drugs Carefully: medically speaking Chiral Drugs Thousands of drugs are marketed throughout the world. The origins of these drugs fall into three categories: Ibuprofen is an analgesic (painkiller) with anti-inflammatory properties. The S enantiomer is the active agent, while the R enantiomer is inactive. Nevertheless, ibuprofen is sold as a mixture of both enantiomers (under the trade names Advil and Motrin), because the benefit of separating the enantiomers is not clear. In fact, there is evidence that the human body is capable of slowly converting the R enantiomer into the desired S enantiomer. Many synthetic drugs are sold as a mixture of enantiomers, because of the high cost and difficulty associated with separating enantiomers. In many cases, enantiomers can trigger entirely different physiological responses. For example, consider the enantiomers of Timolol: 1. natural products-compounds isolated from natural sources, such as plants or bacteria, 2. natural products that have been chemically modified in the laboratory, or 3. synthetic compounds (made entirely in the laboratory). Most drugs obtained from natural sources consist of a single enantiomer. It is important to realize that a pair of enantiomers will rarely exhibit the same potency. We have seen in previous chapters that drug action is usually the result of drug-receptor binding. If the drug binds to the receptor in at least three places (called three-point binding), then one enantiomer of the drug may be more capable of binding with the receptor: OH OH (S)-Timolol (R)-Timolol CO CO2 H The S enantiomer treats angina and high blood pressure, while the R enantiomer is useful in treating glaucoma. In this +NH, +NH

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.22P
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11. Read the article below about the Chiral Drugs Carefully: medically speaking Chiral Drugs Thousands of drugs are marketed throughout the world. The origins of these drugs fall into three categories: Ibuprofen is an analgesic (painkiller) with anti-inflammatory properties. The S enantiomer is the active agent, while the R enantiomer is inactive. Nevertheless, ibuprofen is sold as a mixture of both enantiomers (under the trade names Advil and Motrin), because the benefit of separating the enantiomers is not clear. In fact, there is evidence that the human body is capable of slowly converting the R enantiomer into the desired S enantiomer. Many synthetic drugs are sold as a mixture of enantiomers, because of the high cost and difficulty associated with separating enantiomers. In many cases, enantiomers can trigger entirely different physiological responses. For example, consider the enantiomers of Timolol: 1. natural products-compounds isolated from natural sources, such as plants or bacteria, 2. natural products that have been chemically modified in the laboratory, or 3. synthetic compounds (made entirely in the laboratory). Most drugs obtained from natural sources consist of a single enantiomer. It is important to realize that a pair of enantiomers will rarely exhibit the same potency. We have seen in previous chapters that drug action is usually the result of drug-receptor binding. If the drug binds to the receptor in at least three places (called three-point binding), then one enantiomer of the drug may be more capable of binding with the receptor: OH он (S)-Timolol (R)-Timolol Co H The S enantiomer treats angina and high blood pressure, while the Renantiomer is useful in treating glaucoma. In this example, both enantiomers produce desirable, albeit different, results. In other cases, one enantiomer can produce an unde- sirable response. For example, consider the enantiomers of penicillamine: +NH, +NH, H The first compound (left) can bind with the receptor, while its enantiomer (right) cannot bind with the receptor. For this reason, enantiomers will rarely produce the same biological response. As an example, consider the enantiomers of ibuprofen: HS OH HS OH NH2 NH2 (R)-Penicillamine (S)-Penicillamine or The S enantiomer was used to treat chronic arthritis (until other, more effective drugs were developed), while the R enantiomer is highly toxic. In such a case, the drug cannot be sold as a mixture of enantiomers. HO (S)-lbuprofen (A)Ibuprofen
Transcribed Image Text:11. Read the article below about the Chiral Drugs Carefully: medically speaking Chiral Drugs Thousands of drugs are marketed throughout the world. The origins of these drugs fall into three categories: Ibuprofen is an analgesic (painkiller) with anti-inflammatory properties. The S enantiomer is the active agent, while the R enantiomer is inactive. Nevertheless, ibuprofen is sold as a mixture of both enantiomers (under the trade names Advil and Motrin), because the benefit of separating the enantiomers is not clear. In fact, there is evidence that the human body is capable of slowly converting the R enantiomer into the desired S enantiomer. Many synthetic drugs are sold as a mixture of enantiomers, because of the high cost and difficulty associated with separating enantiomers. In many cases, enantiomers can trigger entirely different physiological responses. For example, consider the enantiomers of Timolol: 1. natural products-compounds isolated from natural sources, such as plants or bacteria, 2. natural products that have been chemically modified in the laboratory, or 3. synthetic compounds (made entirely in the laboratory). Most drugs obtained from natural sources consist of a single enantiomer. It is important to realize that a pair of enantiomers will rarely exhibit the same potency. We have seen in previous chapters that drug action is usually the result of drug-receptor binding. If the drug binds to the receptor in at least three places (called three-point binding), then one enantiomer of the drug may be more capable of binding with the receptor: OH он (S)-Timolol (R)-Timolol Co H The S enantiomer treats angina and high blood pressure, while the Renantiomer is useful in treating glaucoma. In this example, both enantiomers produce desirable, albeit different, results. In other cases, one enantiomer can produce an unde- sirable response. For example, consider the enantiomers of penicillamine: +NH, +NH, H The first compound (left) can bind with the receptor, while its enantiomer (right) cannot bind with the receptor. For this reason, enantiomers will rarely produce the same biological response. As an example, consider the enantiomers of ibuprofen: HS OH HS OH NH2 NH2 (R)-Penicillamine (S)-Penicillamine or The S enantiomer was used to treat chronic arthritis (until other, more effective drugs were developed), while the R enantiomer is highly toxic. In such a case, the drug cannot be sold as a mixture of enantiomers. HO (S)-lbuprofen (A)Ibuprofen
a) Please write down the 5 key massages of the above article b) Why not the two enantiomeric compounds will not give the same biological response? c) "An S enantiomer of Ibuprofen is active agent but R enantiomer is not "what do you mean by that? d) What are the different activities would you find with (S)-Timolol and (R) - Timolol.
Transcribed Image Text:a) Please write down the 5 key massages of the above article b) Why not the two enantiomeric compounds will not give the same biological response? c) "An S enantiomer of Ibuprofen is active agent but R enantiomer is not "what do you mean by that? d) What are the different activities would you find with (S)-Timolol and (R) - Timolol.
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