| Date | November 2016 | Marks available | 1 | Reference code | 16N.3.sl.TZ0.17 |
| Level | SL | Paper | 3 | Time zone | TZ0 |
| Command term | State | Question number | 17 | Adapted from | N/A |
Question
Oseltamivir (Tamiflu) and zanamivir (Relenza) are both used as antivirals to help prevent the spread of the flu virus, but are administered by different methods.
Zanamivir must be taken by inhalation, not orally. Deduce what this suggests about the bioavailability of zanamivir if taken orally.
Oseltamivir does not possess the carboxyl group needed for activity until it is chemically changed in the body. Deduce the name of the functional group in oseltamivir which changes into a carboxyl group in the body. Use section 37 of the data booklet.
The synthesis of oseltamivir is dependent on a supply of the precursor shikimic acid, which is available only in low yield from certain plants, notably Chinese star anise. State one alternative green chemistry source of shikimic acid.
Markscheme
«oral bioavailability is» low
OR
drug is broken down/pH too low/unable to be absorbed from gut
OR
only a small proportion of the drug «taken by mouth» reaches the target organ
ethoxycarbonyl/carbonyl attached to oxygen
Accept “ester”.
Any one of:
fermentation
OR
microbial production
genetically engineered bacteria/E.coli
sweetgum «seeds/leaves/bark»
OR
pine/fir/spruce tree «needles»
OR
Ginkgo biloba
Accept other specific examples of more plentiful plant sources.
Examiners report
Syllabus sections
-
17N.3.hl.TZ0.21c:
Explain the low environmental impact of most medical nuclear waste.
-
17M.3.sl.TZ2.19a:
Suggest one problem associated with chlorinated organic solvents as chemical waste.
-
17N.3.sl.TZ0.16:
Radioisotopes are used to diagnose and treat various diseases. Explain the low environmental impact of most medical nuclear waste.
- 16N.3.hl.TZ0.28d: Outline the nature of the radioactive waste that is generated by the use of technetium-99m in...
- 18N.3.sl.TZ0.12c: Outline one effect of over-prescription of penicillin.
- 19N.3.sl.TZ0.19a: Outline the impact of antibiotic waste on the environment.
-
18N.3.sl.TZ0.16:
Suggest two reasons why chlorinated solvents should neither be released into the atmosphere nor incinerated (burnt).
-
19M.3.sl.TZ2.15e:
Outline two factors which must be considered to assess the greenness of any chemical process.
-
17M.3.sl.TZ1.21c:
Suggest why the administration of antibiotics to humans and animals can affect the environment.
-
18M.3.sl.TZ2.20:
Drug synthesis often involves solvents.
Identify a common hazardous solvent and a Green solvent that could replace it.
- 19N.3.hl.TZ0.25c: Suggest a concern about the disposal of solvents from drug manufacturing.
- 19N.3.hl.TZ0.25b: Outline the impact of antibiotic waste on the environment.
-
17M.3.sl.TZ1.19e:
The pharmaceutical industry is one of the largest producers of waste solvents.
State a green solution to the problem of organic solvent waste.
-
19M.3.hl.TZ2.25a:
Examine the synthesis of taxol in terms of green chemistry criteria.
-
19M.3.sl.TZ1.19b:
Outline the disposal of LLW.
-
19M.3.sl.TZ1.19a:
Outline what is meant by low-level waste.
-
17M.3.sl.TZ2.19b:
Suggest how the principles of green chemistry can be used to solve the environmental problems caused by organic solvents.
-
18M.3.sl.TZ1.13c.iii:
Outline two consequences of prescribing antibiotics such as penicillin unnecessarily.
- 19N.3.sl.TZ0.19b: Suggest a concern about the disposal of solvents from drug manufacturing.
-
17M.3.hl.TZ1.25e:
The pharmaceutical industry is one of the largest producers of waste solvents.
State a green solution to the problem of organic solvent waste.
-
18M.3.sl.TZ1.15b:
Shikimic acid, the precursor for oseltamivir (Tamiflu), was originally extracted from star anise, and is now produced using genetically modified E. coli bacteria.
Suggest one difficulty associated with synthesizing oseltamivir (Tamiflu) from star anise.
-
17M.3.sl.TZ1.21b:
Oseltamivir was commercially produced from shikimic acid, a precursor which is a metabolite in micro-organisms and plants.
Outline how green chemistry was used to develop the precursor for oseltamivir in order to overcome a shortage of the drug during the flu season.
-
20N.3.sl.TZ0.13b:
Outline a green chemistry solution for problems generated by the use of organic solvents.
- 20N.3.sl.TZ0.13a: Describe the proper disposal of low-level radioactive waste in hospitals.
-
20N.3.hl.TZ0.17c:
Describe the proper disposal of low-level radioactive waste in hospitals.
-
19M.3.hl.TZ1.24b(i):
Outline what is meant by low-level waste.
