Aspirin is possibly the most used drug in the world. It has uses in pain relief, reducing inflammation, reducing fever, cardiovascular health and now there are reports on its anti-cancer abilities. However, were it to be discovered and trialled today it would probably not make it to market due to its side effects.
You research task is to uncover the history of aspirin and the role chemists have played in modifying its structure to improve its health benefits. Dig into what aspirin can be prescribed for and if the ‘cure’ is worth the risk of the possible side-effects. Since it’s a chemistry blog, you need to include details on functional groups, the reactions done to modify its structure and the benefits gained. Have a look at the structure of some other related drugs and note any similarities or differences. Who owns aspirin and what is its market worth?
Finally, you need to include details about your own attempted synthesis of aspirin in the form of a brief lab report.
REMEMBER TO CITE ALL OF YOUR SOURCES OF INFORMATION
Year12Chemistry@DykeHouse 
https://kayleighjeffrey.files.wordpress.com/2016/06/aspirin.docx
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Aspirin
Aspirin, one of the first drugs to come into common usage, is still the mostly widely used in the world – approximately 35,000 metric tonnes are produced and consumed annually, enough to make over 100 billion standard aspirin tablets every year. Aspirin in an ingredient in a large number of propriety analgesic and cold/flu preparations. Doctors now also often prescribe it as a valuable medicine to prevent heart attacks and it is under investigation in a number of other medical conditions such as cancer and diabetes.
Everyone has known for years that aspirin is a fast and reliable painkiller that also reduces inflammation and cools fevers. More recently it has become just as well known as a help to people with heart complaints such as angina, coronary thrombosis and after coronary bypass surgery. It is becoming better known, too, in prevention of stroke. Among other diseases in which active research about aspirin is showing great promise – and in which it is now being increasingly used – are toxaemia of pregnancy, diabetes, bowel cancer and dementia.
400BC- In Greece, Hippocrates gave a woman willow leaf tea to relieve some of the pain from childbirth.
1763- the reverend Edward Stone gave dried willow bark to 50 parishioners suffering rheumatic fever.
1823- in Italy, the active ingredient is extracted from willow and named salicin.
1838- Salicin also found in the meadowsweet flower by Swiss and German researchers.
1853- Salicylic acid made from salicin by French scientists, however it is found to irritate the gut.
1893- German scientists find that adding an acetyl group to salicylic acid reduces the irritating properties.
1897- Bayer’s Felix Hoffmann develops a process for synthesising aspirin and the first clinical trials begin.
1899- the clinical trials are successful and aspirin is launched.
1914- International trade in pharmaceuticals interrupted by WW1. Nicholas also finds a new way to produce aspirin.
1974- First evidence of aspirin preventing heart attacks is found.
In 1897, Felix Hoffmann discovered that there was indeed a way to make this drug less irritating to the throat and stomach: by reacting Salicylic acid with Acetic Anhydride, it would be possible to acetylate the Salicylic acid to remove one of the proton-donating groups and thus make it less irritating to the body. The Bayer as Aspirin trademarked this resulting compound, Acetylsalicylic Acid, ®.
Salicyclic acid + Acetic Anhydride -> Aspirin + Acetic Acid
Heart attacks
Aspirin is now accepted as an important weapon in the prevention of heart disease. After the first study by Elwood and Cochrane was reported in the British Medical Journal larger trials involving 20,000 US doctors showed that aspirin reduced the risk of coronary thrombosis by 44 per cent. A single dose of 300 mg is now recommended for patients in the acute stages of a heart attack followed by a daily dose of 75-100 mg. A similar low dose treatment regime is recommended for patients with angina, a history of heart problems or who have undergone coronary by pass surgery.
Strokes
A trial reported in the Lancet this year is the latest in a sequence of studies showing that aspirin reduces the risk of strokes in patients with ‘early warning signs’ of transient ischaemic attacks. Further trials showed a small but definite benefit in reducing mortality in those patients (T.I.A.’s) in the acute phase of a stroke.
Pregnancy Complications
Pre-eclampsia and foetal growth retardation, both caused by blockages of the blood vessels of the placenta, are two of the commonest complications of pregnancy – there are 50,000 cases of pre-eclampsia in Britain a year. In a trial involving more than 9000 women in 16 countries, a daily dose of 60 mg aspirin reduced the risk of pre-eclampsia by 13 per cent. Earlier research suggested that the benefits were even greater.
Colon cancer
In a long term study of 90,000 US nurses between 1976 and 1995, those who took 4-6 tablets of aspirin a week had a reduced incidence of colorectal cancer. The benefits were greatest in those who had taken the drugs the longest.
Diabetes
Blindness, coronary artery disease, stroke and kidney failure are all common complications of diabetes resulting from impaired blood circulation. The benefits of taking one aspirin a day are now so widely accepted that it is considered unethical to perform placebo controlled trials to prove the case.
Dementia (including Alzheimer’s disease)
Some form of dementia affects about one in four people aged 70 years or above. There is some evidence that aspirin may help prevent both the condition resulting from impaired blood flow and the most serious form of dementia, Alzheimer’s disease. The latter is believed to be an inflammatory condition similar to arthritis. Aspirin is a highly effective anti-inflammatory drug and a preliminary study found a lower than expected incidence in patients with rheumatoid arthritis, who frequently have to take aspirin over a prolonged period.
If aspirin was in clinical trial now, it may have not been passed, as a drug in modern medicine due to it’s many side affects. One of the main side affects is gastrointestinal side affects. Gastrointestinal side effects have included epigastric distress (in as many as 83% of patients treated with regular aspirin), abdominal discomfort or pain, endoscopically identifiable gastric mucosal lesions, nausea, and vomiting. More serious gastrointestinal effects include haemorrhage, peptic ulcers, perforation, small bowel enteropathy, and oesophageal ulcerations.
The company who currently own aspirin which has a market worth of $1.1 billion for the sales of aspirin.
Bibliography
.. (2016). History of Aspirin. Available: http://www.aspirin-foundation.com/history-of-aspirin/. Last accessed 20th june 2016.
.. (.). Felix Hoffmann. Available: http://www.chemheritage.org/discover/online…/chemistry-in…/hoffmann.aspx. Last accessed 20th june 2016.
Ali. (2014). Synethesis and characterisation of aspirin. Available: http://www.odinity.com/characterization-of-aspirin/. Last accessed 20th june 2016.
.. (.). side effects of aspirin. Available: https://www.drugs.com/sfx/aspirin-side-effects.html. Last accessed 20th june 2016.
Jonathan Totty
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Aspirin:
An extremely commonly used drug in our society, aspirin has been used as a painkiller for over a century however before this a traditional remedy involved willow. Although it was unknown to the people at the time, willow contains salicin which is now an active and key part of aspirin. Although this association was made around the 1830’s and salicin was developed and synthesised into salicylic acid by 1850, it took until 1897 when Felix Hoffman found that adding an acetyl group reduces the irritant side effects that had been found with salicylic acid. This was the major change to the drug that lead to its growth in popularity as the benefits of helping to reduce fever and joint inflammation in patients with rheumatism. As further trails were done it was shown to have further benefits in pain reduction.
Aspirin is considered useful in multiple ways as it has short term (when taken in high doses) benefits and long terms benefits (when taken in low doses for a long amount of time). At high doses it provides pain relief for multiple types of pain as well as reducing cold and flu symptoms. When taken in the long term sense, it reduces blood clots (due to an antiplatelet effect)which can be helpful for multiple heart issues. While there are clearly some excellent benefits of aspirin, there are also always going to be some negatives that are possible to occur. It may cause a stroke due to a burst blood vessel as well as gastrointestinal bleeding due to it increasing the risk of developing a stomach ulcer. Any current stomach ulcers may bleed further due to aspirin and this could be life threatening. Although this is a major risk, unless a stomach ulcer is present it seems that the pros of taking aspirin much outway the cons.
Aspirin has functional groups of an aromatic group, carboxylic acid and an ester group. Salicin (the naturally occurring substance) also has the aromatic group as well as the ester bond however rather than the carboxylic acid it has an alcohol group. We didn’t do the initial synthesis of salicin in our experiment however if we had it would likely have involved attempting to oxidise the group in order to make the carboxylic acid. Ibruprofen is also similar to aspirin and is extremely popular. In terms of functional groups it has both the carboxylic acid and the aromatic group. For most drugs, the one constant is the aromatic group while the other groups are slightly less important.
Looking back to the initial synthesis of aspirin, when Hoffman developed this method it was patented by his company Bayer. As they own the rights to this they have been extremely successful and although they will have other sources of income they are in the Forbes Top 100 companies and are valued at around $100 billion which shows the value of aspirin.
http://www.nhs.uk/Conditions/Anti-platelets-aspirin-low-dose-/Pages/Introduction.aspx
http://www.pharmaceutical-journal.com/news-and-analysis/features/a-history-of-aspirin/20066661.article
http://www.aspirin-foundation.com/history-of-aspirin/100-years-of-aspirin/
http://www.mayoclinic.org/diseases-conditions/heart-disease/in-depth/daily-aspirin-therapy/art-20046797?pg=2
http://www.forbes.com/companies/bayer/
http://www.ausetute.com.au/aspirin.html
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Aspirin
This was one of the initial drugs to be used by humans and is one of the most commonly used drugs worldwide. The production is massive, and it is estimated that 100 billion tablets could be made each year, and is used with cold and flu tablets. Most drugs need updating every couple of years due to antibodies adapting but aspirin has been effective for a large period of time and looks like it will continue to flourish for the upcoming years. In the past, the usage has a good safety ratio and is very cheap to produce so is the go to drug when it comes to fevers. It is a fast and reliable painkiller and doctors are finding out more about it every day, as recently it was discovered that it can be used to solve heart problems.
It goes all the way back to 400 BC, where the greek used to use it as a painkiller to reduce the pain during pregnancy and has gone all the way to potentially help in the cure of colon cancer alongside many other illnesses. It also has it’s issues, with links to babies having undeveloped hearts, if taken during pregnancy so may not be worth the slight pain relief. There are common side effects, including vomiting, heartburn and nausea, but this is only a small issue when you look at some of the long term problems including loss of hearing and breathing difficulties. This is why many argue that the drug should not be overused and doctors shouldn’t prescribe it for any symptom.
Inside an aspirin molecule, there is 2 main functional groups, carboxylic acid and esters, but is a weak acid. It is known as an aromatic compound due to it’s benzene ring with the double bond alternating in positions. Roxiprin is a similar drug and contains aspirin, and many of the side effects are the same showing a link in the two, suggesting that there is problems when using the functional groups in medicine.
Lab report
In our experiment, we found that the 3 dots for the crystals we formed stayed in the same line, and that our product had a similar boiling point to the tablet made industrially. This shows the quality of the experiment was to a high standard and that our results were accurate. Our yield however was often low as we had a high theoretical yield but didn’t manage to reach it due to multiple reasons. First off, we may have had equipment errors such as inaccurate readings leading to different results, and also we could have not used the full amount by leaving some of it in the test tube or beaker by accident when mixing compounds. We had to recrystallize our aspirin to remove the impurities and is based on the temperature change and the solubility of the compound. We also used vacuum filtration to remove the crystals from the solution so some crystals may of been lost of the filter paper but this separated the crystals and allowed us to continue in the experiment.
http://www.everydayhealth.com/drugs/aspirin
http://www.ausetute.com.au/aspirin.html
https://www.mskcc.org/cancer-care/patient-education/common-medications-containing-aspirin-and-other-nonsteroidal-anti-inflammatory-drugs-nsaids
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Aspirin
Emily Kirkham
Aspirin was discovered by Felix Hoffmann in an attempt to substitute the commonly used sodium salicylate, which acted like a non-steroidal anti-inflammatory drug (NSAID) that induced apoptosis (cell death) in cancer cells. However the effects were so unpleasant an alternative was needed. In Germany the first pure sample of acetylsalicylic acid was made and was marketed in 1899 as the drug aspirin. Hoffmann and Dresser decided that although its acidic taste it was not corrosive and was therefore safer to the public, but due to the original sentence in German being translated into English it was misinterpreted that it had been tested, not about to be tested.
Before Hoffmann developments began in 1763 with Edward stone who studied the effects of fever and malaria with willow bark. By 1830 a Scot discovered the positive effects of the willow bark, which relieved acute rheumatism. In 1840 scientists detached the ingredient, which seemed to provide the great effects called salicin. This was presented, in 1870, when a professor conveyed the conversion of salicin to salicylic acid. This was given to patients to reduce pain levels but tasted awful.
The effects of aspirin have proven to be very helpful. It has been found to reduce the cancer risk in a study in 2014, as well as reducing blood pressure (which aids in reducing the risk of stroke or heat attack), inflammation and as a pain relief by blocking neurotransmitters across the synapse. It is also described as antipyretic (reducing fever). It works by focusing on prostaglandins, which are fatty acid chains, to reduce pain.
However there are many side affects, some of which are: Upset stomach, heart burn, vomiting, easy bleeding or bruising, difficulty hearing, changes in amount of urine, dizziness, tiredness and yellowing of the skin. It can also cause internal bleeding particularly of the stomach and lead to ulcers. Despite the large amount of side effects it is said to out way the side effects if used in small doses. If there is a history of strokes and or heart attacks then doctors could recommend taking a tablet daily to reduce the risk of another, however it is not advised to take daily if no serious risk is present.
Aspirin is a weak acid, which is very lightly soluble in water due to it being non-polar. Adding NaOH can increase solubility, which makes ingesting it easier and quicker for it to get into blood stream. It is an aromatic compound meaning its cyclic (having a benzene ring), containing a carboxylic acid and an ester. Because it’s acidic, this means the Ph is less than 7, giving H+ ions. Because of H bonds it is slightly soluble.
C7H6O3 (salicylic acid)+ C4H6O3 (Ethanoic anhydride) => C9H8O4 or aspirin.
A company called Bayer owns aspirin and it is very cheap at £0.55 for 32 tablets Its very affordable but perhaps paracetamol is a better alternative.
http://www.mayoclinic.org/diseases-conditions/heart-disease/in-depth/daily-aspirin-therapy/art-20046797
http://www.pharmaceutical-journal.com/news-and-analysis/infographics/a-history-of-aspirin/20066661.article
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1119266/
http://www.rxlist.com/aspirin-side-effects-drug-center.htm
Click to access Aspirin.pdf
http://www.boots.com/en/Boots-Aspirin-300mg-Tablets-32-Tablets_1178966/
http://www.bayer.com/en/history.aspx
https://prezi.com/6126lq1u4kpa/the-science-behind-the-aspirin/
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