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“Chemistry in the News”

Chapter 24 Phenols – Section 14 Quinones

Government threatens to suspend patent on Cipro

USA Today

Associated Press

Editorial Comments

Bayer, the corporation that made its mark in the pharmaceutical communnity by the introduction of aspirin is now facing a crisis just like the one it previously faced during the First World War, a possible removal of a US patent for a drug that it invented. Ciprofloxacin, or commonly known as Cipro, is an antibacterial drug known most recently as one of the drugs approved to treat inhalation Anthrax, a bacterial infection that quickly replicates and destroys the host. With the recent terrorist activities involving Anthrax, the demand for Cipro has skyrocketed and cannot be met by the Bayer Corporation, even after they tripled production. The US and Canadian governments have given thought to removing the patent on Cipro, which is owned by Bayer, so that the demand for the drug can be met.

Cipro is a type of pharmaceutical known as Fluoroquinones, which result from the oxidation of phenols. The fluoroquinone functional group is the active site of the drug that stops the replication, repair, and transcription of bacterial DNA by inhibition of the DNA gyrase enzyme. DNA gyrase, also known as topoisomerase II, is an enzyme that unwinds the DNA Helix so that the DNA polymerase complexes can replicate the genetic sequence without supercoiling. By inhibiting this enzyme, cipro effectively prevents the bacteria from reproducing. Cipro also inhibits the action of topoisomerase IV, which distributes the chromosomal ring DNA of the bacteria during replication and cell wall division.

With biological terrorism on the rise and the proven antibacterial effectiveness of Cipro, removal of the patent may be necessary so that enough antibacterial agents can be produced to meet the immediate demands of those infected.

Questions:

1. Find the chemical structure for Ciprofloxacin and paste it here? Give the IUPAC name for this compound and state what type of compound this is.

A:

[pic]

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

It is a quinoline carboxylic acid.

2. Many pharmaceutical drugs include a salt. What is the significance of this salt, how is it formed, and which salt is used with Cipro (not seen in the chemical structure of cipro on chemfinder)?

A: this drug and uses an HCl salt to facilitates its uptake by making the drug more water-soluble. This allows the body to readily take up the drug. This salt is formed when the cooh or carboxylic acid group reacts with an amine.

3. Cipro is what type of drug and what is the mechanism of action for these drugs?

A: Cipro is a fluoroquinone and it inhibits both Topoisomerase II and topoisomerase IV. Cipro inhibits the formation of Topoisomerase II, which allows for the replication of the Bacterial DNA by unwinding the double-helix and prevention of supercoiling. Topoisomerase IV equally splits up the chromosomal ring of DNA to new daughter cells. These inhibitions result in the stop of replication and death of the bacterial cell.

4. Name some possible ways in which Anthrax is transmitted? Is Anthrax a virus? Is Anthrax treatable by Ciprofloxacin and if so what are the possible side effects of taking this drug?

A: Eating raw meat, contact with animal fur, inhalation of spores, and cutaneous skin exposure can all cause lead to an Anthrax infection. Anthrax cannot be passed on by contact with a contaminated person. No, Anthrax is a bacterial infection and can be treated by Ciprofloxacin. The possible side effects of Cipro are stomach pain, upset stomach, diarrhea, vomiting, nausea, restlessness, change in sensitivity of skin to sun light, change in sense of taste, blistering of skin, burning of skin, itching or rashes.

The CIITN project was a very worthwhile group assessment of organic chemistry in our society today. It allowed the members of our group, who did not know each as well before the project, to get to know one another better. We had multiple meetings where we were able to concentrate our attention and ideas in a relaxed setting. We threw around many ideas and finally came to rest on the topic discussed above, ciproflaxin. Each of our members contributed an incredible amount to the success of our project. Craig discovered the article and did a vast amount of research, which we discussed, and Adam was able to find all kinds of links related to the topic. Ben researched other CIITN projects and came up with the format that we felt best for our project as well as doing a good amount of research along with Craig. We all came together the final night to come with four challenging questions and to polish up the final draft for submission. The final result is a product of our hard work together, and exemplifies our willingness to excel in the field of organic chemistry.

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