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Paracetamol, also known as acetaminophen or APAP, is a medicine used to treat pain and fever.
Paracetamol is generally safe at recommended doses.
Paracetamol was first made in 1877.
Contents
1 Medical uses
1.1 Fever
1.2 Pain
1.2.1 Osteoarthritis
1.2.2 Low back pain
1.2.3 Headaches
1.2.4 Postoperative pain
1.2.5 Dental use
1.2.6 Other
1.3 Patent ductus arteriosus
2 Adverse effects
2.1 Liver damage
2.2 Skin reactions
2.3 Asthma
2.4 Other factors
2.5 Overdose
2.6 Pregnancy
2.7 Cancer
3 Pharmacology
3.1 Mechanism of action
3.2 Pharmacokinetics
4 Chemistry
4.1 Chemical properties
4.2 Synthesis
4.2.1 Original (Boots) method
4.2.2 Green synthesis
4.2.3 Direct synthesis
4.3 Reactions
5 History
6 Society and culture
6.1 Naming
6.2 Cost
6.3 Available forms
6.4 Controversy
7 Veterinary use
7.1 Cats
7.2 Dogs
7.3 Snakes
8 References
9 External links
Medical uses
Fever
Paracetamol is used for reducing fever in people of all ages. Paracetamol does not have significant anti-inflammatory effects.
Pain
Paracetamol is used for the relief of mild to moderate pain.
Osteoarthritis
The American College of Rheumatology recommends paracetamol as one of several treatment options for people with arthritis pain of the hip, hand, or knee that does not improve with exercise and weight loss.
Paracetamol has relatively little anti-inflammatory activity, unlike other common analgesics such as the nonsteroidal anti-inflammatory drugs (NSAIDs), aspirin, and ibuprofen, but ibuprofen and paracetamol have similar effects in the treatment of headache. Paracetamol can relieve pain in mild arthritis, but has no effect on the underlying inflammation, redness, and swelling of the joint. It has analgesic properties comparable to those of aspirin, while its anti-inflammatory effects are weaker. It is better tolerated than aspirin due to concerns about bleeding with aspirin.
Low back pain
Based on a systematic review, paracetamol is recommended by the American Pain Society as a first-line treatment for low back pain.
Headaches
A joint statement of the German, Austrian, and Swiss headache societies and the German Society of Neurology recommends the use of paracetamol in combination with caffeine as one of several first-line therapies for treatment of tension or migraine headache.
Postoperative pain
Paracetamol combined with NSAIDs may be more effective for treating postoperative pain than either paracetamol or NSAIDs alone.
Dental use
NSAIDs such as ibuprofen, naproxen, and diclofenac are more effective than paracetamol for controlling dental pain or pain arising from dental procedures; combinations of NSAIDs and paracetamol are more effective than either alone.
Other
The efficacy of paracetamol when used in combination with weak opioids (such as codeine ) improved for about 50% of people, but with increases in the number experiencing side effects.
The combination of paracetamol with caffeine is superior to paracetamol alone for the treatment of common pain conditions, including dental pain, post partum pain, and headache.
Patent ductus arteriosus
Paracetamol is used to treat patent ductus arteriosus, a condition that affects newborns when a blood vessel used in developing the lungs fails to close as it normally does, but evidence for the safety and efficacy of paracetamol for this purpose is lacking.
Adverse effects
Healthy adults taking regular doses up to 4,000 mg a day shows little evidence of toxicity (although some researchers disagree
Liver damage
Acute overdoses of paracetamol can cause potentially fatal liver damage. In 2011, the U.S. Food and Drug Administration launched a public-education program to help consumers avoid overdose, warning: “Acetaminophen can cause serious liver damage if more than directed is used.” The overdose risk may be heightened by frequent consumption of alcohol.
Paracetamol toxicity is the foremost cause of acute liver failure in the Western world, and accounts for most drug overdoses in the United States, the United Kingdom, Australia, and New Zealand.
Paracetamol is metabolised by the liver and is hepatotoxic ; side effects are multiplied when combined with alcoholic drinks, and are very likely in chronic alcoholics or people with liver damage.
Skin reactions
On August 2, 2013, the FDA issued a new warning about paracetamol. It stated that the drug could cause rare and possibly fatal skin reactions such as Stevens–Johnson syndrome and toxic epidermal necrolysis. Prescription-strength products will be required to carry a warning label about skin reactions, and the FDA has urged manufacturers to do the same with over-the-counter products.
Asthma
An association exists between paracetamol use and asthma, but whether this association is causal is still debated as of 2017.
As of 2014, the American Academy of Pediatrics and the National Institute for Health and Care Excellence continue to recommend paracetamol for pain and discomfort in children,
Other factors
In contrast to aspirin, paracetamol does not prevent blood from clotting (it is not an antiplatelet ), thus may be used in people who have concerns with blood coagulation. Additionally it does not cause gastric irritation.
Overdose
Main article: Paracetamol toxicity
Untreated paracetamol overdose results in a lengthy, painful illness. Signs and symptoms of paracetamol toxicity may initially be absent or non-specific symptoms. The first symptoms of overdose usually begin several hours after ingestion, with nausea, vomiting, sweating, and pain as acute liver failure starts. The process of dying from an overdose takes from 3–5 days to 4–6 weeks.
Paracetamol hepatotoxicity is by far the most common cause of acute liver failure in both the United States and the United Kingdom.
Untreated overdose can lead to liver failure and death within days. Treatment is aimed at removing the paracetamol from the body and replenishing glutathione. Kidney failure is also a possible side effect.
Until 2004, tablets were available (brand-name in the UK Paradote) that combined paracetamol with an antidote ( methionine ) to protect the liver in case of an overdose. One theoretical, but rarely if ever used, option in the United States is to request a compounding pharmacy to make a similar drug mix for people who are at risk.
In June 2009, an FDA advisory committee recommended that new restrictions be placed on paracetamol use in the United States to help protect people from the potential toxic effects. The maximum dosage at any given time would be decreased from 1000 mg to 650 mg, while combinations of paracetamol and opioid analgesics would be prohibited. Committee members were particularly concerned by the fact that the then-present maximum dosages of paracetamol had been shown to produce alterations in hepatic function.
In January 2011, the FDA asked manufacturers of prescription combination products containing paracetamol to limit its amount to no more than 325 mg per tablet or capsule and began requiring manufacturers to update the labels of all prescription combination paracetamol products to warn of the potential risk of severe liver damage.
In November 2011, the Medicines and Healthcare products Regulatory Agency revised UK dosing of liquid paracetamol for children.
Pregnancy
Experimental studies in animals and cohort studies in humans indicate no detectable increase in congenital malformations associated with paracetamol use during pregnancy.
Paracetamol use by the mother during pregnancy is associated with an increased risk of childhood asthma.
Cancer
Some studies have found an association between paracetamol and a slight increase in kidney cancer,
Pharmacology
Mechanism of action
AM404  – Metabolite of paracetamol
Anandamide  – Endogenous cannabinoid
The mechanism of action of paracetamol is not completely understood. Unlike NSAIDs such as aspirin, paracetamol does not appear to inhibit the function of any cyclooxygenase (COX) enzyme outside the central nervous system, and this appears to be the reason why it is not useful as an anti-inflammatory.
Paracetamol apparently might modulate the endogenous cannabinoid system in the brain through its metabolite, AM404, which appears to inhibit the reuptake of the endogenous cannabinoid/vanilloid anandamide by neurons, making it more available to reduce pain. AM404 also appears to be able to directly activate the TRPV1 (older name: vanilloid receptor), which also inhibits pain signals in the brain.
Pharmacokinetics
Main pathways of paracetamol metabolism (click to enlarge) : Pathways shown in blue and purple lead to nontoxic metabolites; the pathway in red leads to toxic NAPQI.
After being taken by mouth, it is rapidly absorbed by the gastrointestinal (GI) tract (although absorption through the stomach is negligible);
Paracetamol is metabolised primarily in the liver, into toxic and nontoxic products. Three metabolic pathways are notable:
Glucuronidation (45-55%),
Sulfation (sulfate conjugation) (20–30%)
N -hydroxylation and dehydration, then glutathione conjugation, (less than 15%). The hepatic cytochrome P450 enzyme system metabolises paracetamol (mainly CYP2E1 ), forming a minor yet significant alkylating metabolite known as NAPQI ( N -acetyl- p -benzoquinone imine) (also known as N -acetylimidoquinone).
All three pathways yield final products that are inactive, nontoxic, and eventually excreted by the kidneys. In the third pathway, however, the intermediate product NAPQI is toxic. NAPQI is primarily responsible for the toxic effects of paracetamol; this constitutes an example of toxication.
Chemistry
Chemical properties
Paracetamol molecule polar surface area
Paracetamol electrostatic potential map
Paracetamol consists of a benzene ring core, substituted by one hydroxyl group and the nitrogen atom of an amide group in the para (1,4) pattern. The amide group is acetamide (ethanamide). It is an extensively conjugated system, as the lone pair on the hydroxyl oxygen, the benzene pi cloud, the nitrogen lone pair, the p orbital on the carbonyl carbon, and the lone pair on the carbonyl oxygen are all conjugated. The presence of two activating groups also make the benzene ring highly reactive toward electrophilic aromatic substitution. As the substituents are ortho, para -directing and para with respect to each other, all positions on the ring are more or less equally activated. The conjugation also greatly reduces the basicity of the oxygens and the nitrogen, while making the hydroxyl acidic through delocalisation of charge developed on the phenoxide anion.
Paracetamol is part of the class of drugs known as ” aniline analgesics”; it is the only such drug still in use today.
Synthesis
Original (Boots) method
The original method for production involves the nitration of phenol with sodium nitrate gives a mixture of two isomers, from which the wanted 4-nitrophenol (bp 279 °C) can easily be separated by steam distillation. In this electrophilic aromatic substitution reaction, phenol’s oxygen is strongly activating, thus the reaction requires only mild conditions as compared to nitration of benzene itself. The nitro group is then reduced to an amine, giving 4-aminophenol. Finally, the amine is acetylated with acetic anhydride.
Green synthesis
An alternative industrial synthesis developed by Hoechst – Celanese involves direct acylation of phenol with acetic anhydride catalyzed by HF, conversion of the ketone to a ketoxime with hydroxylamine, followed by the acid-catalyzed Beckmann rearrangement to give the amide.
Direct synthesis
More recently (2014) a “one-pot” synthesis from hydroquinone has been described before the Royal Society of Chemistry. The process may be summarized as follows:
Hydroquinone, ammonium acetate, and acetic acid were mixed in an argon atmosphere and heated slowly to 230 °C. The mixture was stirred at this temperature for 15 hours. After cooling the acetic acid was evaporated and the precipitate was filtered, washed with water and dried to give paracetamol as a white solid.
The authors go on to claim an 88% yield and 99% purity.
Reactions
4 -Aminophenol may be obtained by the amide hydrolysis of paracetamol. 4 -Aminophenol prepared this way, and related to the commercially available Metol, has been used as a developer in photography by hobbyists.
History
Julius Axelrod (pictured) and Bernard Brodie demonstrated that acetanilide and phenacetin are both metabolised to paracetamol, which is a better tolerated analgesic.
Acetanilide was the first aniline derivative serendipitously found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the name of Antifebrin by A. Cahn and P. Hepp in 1886.
Paracetamol is the active metabolite of phenacetin and acetanilide, both once popular as analgesics and antipyretics in their own right.
Von Mering’s claims remained essentially unchallenged for half a century, until two teams of researchers from the United States analyzed the metabolism of acetanilide and paracetamol.
Paracetamol was first marketed in the United States in 1950 under the name Triagesic, a combination of paracetamol, aspirin, and caffeine.
Available without a prescription since 1959,
Society and culture
Naming
Acetaminophen is the name generally used in the United States ( USAN ), Japan ( JAN ), Canada In some contexts, such as on prescription bottles of painkillers that incorporate this medicine, it is simply abbreviated as APAP, for a cetyl- p ara- a mino p henol.
Both acetaminophen and paracetamol come from a chemical name for the compound: para – acet yl aminophen ol and par a – acet yl am inophen ol.
Cost
The wholesale price in the developing world is less than 0.01 USD per dose.
In the UK, paracetamol is one of the most prescribed drugs by the NHS.
Available forms
See also: Paracetamol brand names
Tylenol 500 mg capsules Panadol 500 mg tablets For comparison: The pure drug is a white crystalline powder.
Paracetamol is available in a tablet, capsule, liquid suspension, suppository, intravenous, intramuscular and effervescent forms.
In some formulations, paracetamol is combined with the opioid codeine, sometimes referred to as co-codamol ( BAN ) and Panadeine in Australia. In the U.S., this combination is available only by prescription, while the lowest-strength preparation is over the counter in Canada, and in other countries other strengths may be available over the counter.
Paracetamol is commonly used in multi-ingredient preparations for migraine headache, typically including butalbital and paracetamol with or without caffeine, and sometimes containing codeine.
Paracetamol is sometimes combined with phenylephrine hydrochloride. is added to this combination.
When marketed in combination with diphenhydramine hydrochloride, it is frequently given the label “PM” and is meant as a sleep aid. Diphenhydramine hydrochloride is known to have hypnotic effects and is non-habit forming. Unfortunately it has been implicated in the occasional development of restless leg syndrome.
Controversy
In September 2013, an episode of This American Life titled “Use Only as Directed” alleging that the “FDA has long been aware of studies showing the risks of acetaminophen. So has the maker of Tylenol, McNeil Consumer Healthcare, a division of Johnson & Johnson” and “McNeil, the maker of Tylenol,… has repeatedly opposed safety warnings, dosage restrictions and other measures meant to safeguard users of the drug.”
A report prepared by an internal FDA working group describes a history of FDA initiatives designed to educate consumers about the risk of paracetamol overdose and notes that one challenge to the Agency has been “identifying the appropriate message about the relative safety of acetaminophen, especially compared to other OTC pain relievers (e.g., aspirin and other NSAIDs)”. The report notes that “Chronic use of NSAIDs is also associated with significant morbidity and mortality. NSAID gastrointestinal risk is substantial, with deaths and hospitalization estimated in one publication as 3200 and 32,000 per year respectively. Possible cardiovascular toxicity with chronic NSAID use has been a major discussion recently”, finally noting that “The goal of the educational efforts is not to decrease appropriate acetaminophen use or encourage substitution of NSAID use, but rather to educate consumers so that they can avoid unnecessary health risks.”
Veterinary use
Cats
Paracetamol is extremely toxic to cats, which lack the necessary UGT1 enzyme to break it down safely. Initial symptoms include vomiting, salivation, and discoloration of the tongue and gums.
Unlike an overdose in humans, liver damage is rarely the cause of death; instead, methemoglobin formation and the production of Heinz bodies in red blood cells inhibit oxygen transport by the blood, causing asphyxiation ( methemoglobemia and hemolytic anemia ).
Treatment with N-acetylcysteine, methylene blue or both is sometimes effective after the ingestion of small doses of paracetamol.
Dogs
Although paracetamol is believed to have no significant anti-inflammatory activity, it has been reported to be as effective as aspirin in the treatment of musculoskeletal pain in dogs.
A paracetamol-codeine product (trade name Pardale-V)
The main effect of toxicity in dogs is liver damage, and GI ulceration has been reported.
Snakes
Paracetamol is lethal to snakes, and has been suggested as a chemical control program for the invasive brown tree snake ( Boiga irregularis ) in Guam.

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