You came across an article debating the use of Prevacid® vs. Nexium®. While both drugs have the same therapeutic effect, one is sold as a racemate and the other is sold as a single enantiomer. Previous medications such as Thalidomide and Advair® have sparked a debate about the safety of drugs sold as a racemate. 4. What is a racemate?

You came across an article debating the use of Prevacid® vs. Nexium®. While both drugs have the same therapeutic effect, one is sold as a racemate and the other is sold as a single enantiomer. Previous medications such as Thalidomide and Advair® have sparked a debate about the safety of drugs sold as a racemate. 4. What is a racemate?

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.57P

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You came across an article debating the use of Prevacid® vs. Nexium®. While both drugs have the same therapeutic effect, one is sold as a racemate and the other is sold as a single enantiomer. Previous medications such as Thalidomide and Advair® have sparked a debate about the safety of drugs sold as a racemate. 3. What is an enantiomer? Give example
Many studies have shown that one specific enantiomer of citalopram (“S”) is the one capable of inhibition of serotonin reuptake. Lexapro is the brand name for the purified form of the S- enantiomer of citalopram. Explain briefly why Lexapro would be more expensive than Celexa.
Trabectedin, shown in a ball-and-stick model on the cover of this text, is an anticancer drug sold under the trade name Yondelis. a. Locate the stereogenic centers in trabectedin. b.What is the maximum number of stereoisomers possible for trabectedin? c.Draw the enantiomer. d.Draw a diastereomer. e.If the specific rotation of trabectedin is +41.5, what is the [α] of a solution that contains 75% trabectedin and 25% of its enantiomer?f . What is the ee of a solution with [α] = +10.5?
The LD50 (“Lethal Dose, 50 %”) is a value used in toxicology which gives the amount of a substance required to kill 50 % of a test population. It is usually reported based on body weight. For racemic carvone LD50 is reported as 1640 mg/kg. 1. Would it consider carvone to be toxic to an average person? Explain. 2. Would it be expected this the LD50 value to be the same for each enantiomer? Explain at the molecular level in stereochemical terms.
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
What is going on from compound B to compound C? Can you please select all the options that apply
Captopril is a drug used to treat high blood pressure and congestiveheart failure.Draw the enantiomer of captopril
Draw out the reaction that takes place between phenylsuccinic acid and proline as well as the second reaction with HCl. Indicate stereocenters and label them. [Hint: if you look up (-)-proline on Sigma, it will also say if it is R or S, and you can do the same for phenylsuccinic acid.] You can abbreviate phenyl rings as Ph.
Which of the following statements is True for a racemic drug that hasER of 8 for the pharmacological activity? A. The distomer is almost as active as the eutomer. B. The distomer is essentially inactive. C. The eutomer and the distomer contribute equally to the activity.
For the given below ee values, calculate the percentage of each enantiomer present. 60% ee
A chiral amine A having the R conguration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?
2. After an attempt to resolve a racemate into its enantiomers, the observed rotation is +22.4 degrees per g/L. If the known specific rotation is +24.2 degrees per g/L,, what is the % enantiomeric excess of the compound?