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Section D1: Pharmaceutical Products and Drug Actionplacebothalidomideparenteraladdictiontherapeutic indextherapeutic windowtoleranceLD50, ED50 and TD50dosagebioavailability1. Discuss the three different ways in which drugs can be administered by injection. State three other ways in which drugs can be administered.2. The therapeutic window gives information on the amount of a drug that can be safely administered to give the desired effect without causing adverse harm. It is effectively the safety range of the drug and is related to the therapeutic index.Therapeutic index = LD50 / ED50. Explain what is meant by Effective Dose 50 and Lethal Dose 50 and discuss the problems associated with determining the LD50.3. Discuss the term ‘side effects’ in relation to the two drugs aspirin and morphine.4. Explain why morphine is usually administered as a salt (morphine sulfate or morphine hydrochloride) rather than in its pure form.5. The image below shows a child victim of thalidomide. Discuss why the ‘thalidomide story’ was more of a scandal than simply a tragedy.Section D2: Aspirin and Penicillinanalgesicsynergyantibioticantibacterialanticoagulantbeta-lactam ringoverprescriptionsalicylic acid (2-hydroxybenzoic acid)1. (a) State what is meant by the term analgesic and explain the difference in the mode of action of mild and strong analgesics.(b) Identify two functional groups attached to the phenyl group in a molecule of aspirin.(c) State one beneficial effect (other than its analgesic action) and one side effect of aspirin.2. Two different esters that can be synthesized from salicylic acid (2-hydroxybenzoic acid) are acetyl salicylate (aspirin) and methyl salicylate (also known as 'oil of wintergreen').(a) State the equations for both of these syntheses using structural formulas.(b) Identify the catalyst that is used in both cases.3. Aspirin shows two absorptions in the region 1700-1750 cm-1 in its infrared spectrum. These two absorptions are due to the two different carbonyl groups (C=O). Explain why they do not both occur at exactly the same frequency.4. Amoxillin is a general purpose antibiotic used to treat bacterial infections. It has the following structural formula:(a) Draw a circle around the beta-lactam ring.(b) Identify three functional groups present in the molecule that are outside the beta-lactam ring.(c) State two advantages of administering amoxillin compared to the original penicillin, which was known as penicillin G.(d) Explain how amoxillin works as an antibacterial.(e) Explain why amoxillin on its own is not very effective against tuberculosis (a disease caused by the Mycobacterium tuberculosis bacterium).5. (a) The discovery of penicillin is usually attributed to Sir Alexander Fleming. Describe how he first made the discovery and describe the later work done by Howard Florey and Ernst Chain to bring penicillin to the masses during World War II.(b) Some people claim that penicillin was discovered earlier by a Costa Rican called Clodomiro Picado Twight. Identify one other scientific discovery where there is doubt about who first made the discovery and suggest why conflicting claims sometimes arise.6. State one disadvantage of overprescribing penicillins.D3 Opiatesmorphinediamorphine (heroin)codeineopiatelipidsemi-synthetic1. Morphine is a naturally occurring analgesic that can be converted into diamorphine (heroin).(a) Identify the type of reaction occurring during this process.(b) Name the reagent used to react with morphine to convert it into diamorphine.(c) Identify the catalyst needed for this reaction.(d) Explain what is meant by developing a tolerance towards heroin and state why this is dangerous.(e) Explain why in some countries the authorities provide free syringes to heroin addicts.2. The structures of both morphine and heroin are given in Section 37 of the IB chemistry data booklet. Explain why heroin is much less polar than morphine and how this affects its potency as an analgesic.3. The structure of morphine is shown below.(a) Explain why morphine is often administered as its hydrochloride salt.(b) Show where the positive charge will be located when morphine is converted into its hydrochloride salt.4. Explain why iodomethane is used to synthesise codeine from morphine.D4 pH Regulation of the StomachdyspepsiaantacidmetaboliteHenderson-Hasselbalch equationranitidineomeprazoleesomeprazoleH2 receptor antagonistproton pump inhibitor1. Give the equations for the reactions of aluminum hydroxide, magnesium hydroxide and sodium hydrogencarbonate with hydrochloric acid.2. Two well known antacids go by the name of ‘Tums’ and ‘Milk of magnesia’. Tums are essentially calcium carbonate and Milk of magnesia is essentially magnesium hydroxide. If stomach acid has a pH of 2 calculate the mass of calcium carbonate required to neutralize 10 cm3 of stomach acid. Would more or less magnesium hydroxide (in grams) be required to neutralize the same amount of acid?3. (a) Explain how heartburn is caused.(b) One medicine that is stated to be safe for pregnant women to take hasthe trade name ‘Gaviscon cool’. The active ingredients in Gaviscon cool aresodium alginate, sodium hydrogencarbonate and calcium carbonate.The advertising for Gaviscon states that it:“forms a 'raft' over the stomach contents which helps prevent acid coming back up into the esophagus (food pipe). As such it is effective at treating the classic symptoms of heartburn (a burning pain in the chest and mild acid regurgitation)."Identify the ingredient that helps to “form a ‘raft’ over the stomach contents”.4. Two drugs used to treat dyspepsia are ranitidine and omeprazole which are marketed under the trade names of Zantac and Prilosec respectively. Explain the different ways in which these two drugs function in the body.5. The pKa value for ethanoic acid is 4.76. Calculate the pH of the buffer solution formed when:(a) 25.0 cm3 of 0.100 mol dm-3 sodium ethanoate solution is added to 50.0 cm3 of 0.100 mol dm-3 ethanoic acid solution.(b) 0.500 g of sodium ethanoate is added to 50.0 cm3 of 0.100 mol dm-3 sodium ethanoate solution (assume no volume change occurs when the salt is added).D5: Antiviral Medicationcapsidcapsomeracycloviramantadinehuman immunodeficiency virusacquired immune deficiency syndrome (AIDS)T-helper cellAZT1. Discuss the essential differences between a bacterium and a virus.2. State two reasons why it is difficult to treat viral diseases effectively with antiviral drugs.3. Drugs like acyclovir and ganciclovir are two drugs used to treat diseases caused by the herpes virus.Describe the two main ways in which anti-viral drugs can fight specific viral infections.4. AZT (azidothymidine) is used to treat HIV. Identify the three circled functional groups labeled A, B and C contained within a molecule of AZT.5. The structures of oseltamivir (Tamiflu) and zanamivir (Relenza), two dugs used to combat influenza, are given in Section 37 of the data booklet. Identify which:(a) contains an ester group(b) contains a non-cyclic ether group(c) contains a carboxyl group(d) could be classified as an alcoholD6: Environmental Impact of Some Medicationslow-level nuclear waste, LLWhigh-level nuclear waste, HLWgreen chemistryatom economyprecursor1. Discuss how the following have contributed to some bacteria, which cause disease in humans, becoming highly resistant to antibiotics.(a) Non-completion of a prescribed course of antibiotics.(b) The addition of antibiotics to animal food to promote healthy livestock.2. Explain the factors that determine whether nuclear waste is classified as low-level or high-level nuclear waste.3. Outline how the following contaminated substances might be treated:(a) paper and protective clothing used during an investigation with a radioactive isotope to monitor how a patient’s kidney is functioning.(b) a concentrated solution of technetium-99m, a metastable radionucleotide with a half-life of 6 hours, used to monitor kidney function.(c) A spent reactor of cobalt-60, which has been used in external radiotherapy. (Co-60 emits beta and gamma radiation and has a half-life of 5.3 years.)4. Each year many IB Diploma students use an organic solvent to extract caffeine from coffee or tea as part of the experimental work for their extended essay or individual scientific investigation. Explain why in industry supercritical carbon dioxide has mainly replaced organic solvents to extract caffeine and other substances, such as essential oils, from plant material.5. There is a high demand for stocks of Tamiflu whenever an outbreak of a new influenza virus, such as “bird flu”, occurs. Tamiflu is a synthetic drug obtained by a multi-step synthesis using a compound called shikimic acid as the precursor. Shikimic acid can be obtained from the Chinese star anise plant.Explain why much of the shikimic acid required to make Tamiflu is now obtained using genetically modified bacteria. ................
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