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Acetaminophen

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Acetaminophen
Acetaminophenstructure.jpgAcetaminophenBallandStickmodel.jpg
General
Systematic name N-(4-hydroxyphenyl)ethanamide
Other names Paracetamol
Molecular formula C8H9NO2
SMILES O=C(O)Nc1ccc(O)cc1
Molar mass Molar mass:: 151.17 g/mol
Appearance White crystalline powder
CAS number CAS number::103-90-2
Properties
Density and phase Density::1.3 g/ml, Solid
Solubility in water 1.4 g/100 ml (20°C)
Miscible with water and ethanol
Melting point Melting point::170°C
Boiling point Boiling point::500°C
Acidity (pKa) 9.71
Structure
Molecular shape Trigonal bipyramidal
Crystal structure Trigonal and close packed
Dipole moment Polar molecule (moment unknown)
Hazards
MSDS Material safety data sheet
Main hazards May combust at high temp.
Risk of explosion in
presence of mechanical impact
or static discharge.
NFPA 704

NFPA 704 svg.png

1
1
0
 
Flash point 188.4°C
R/S statement R: R10, R36/38
S: S15, S24/25
RTECS number AE4200000
Related compounds
Related Antipyretics Codeine
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Acetaminophen is an analgesic (pain-reliever) that is used all over the world. It is commonly known for being consumed to help relieve headaches, fevers, joint pain, and various other things. It was discovered in the late 1800's and wasn't finalized until Bernard Brodie and Julius Axelrod determined that acetaminophen was a metabolite for both acetanilide and phenacetin. Then in 1956, Acetaminophen was first distributed and sold in bottles of 500 mg pills in the United Kingdom. It is also known as paracetamol and has many similarities to aspirin and ibuprofen. [1]

Properties

Acetaminophen is an unscented, white crystalline powder that has a slightly acidic and bitter taste. It is soluble in methanol and ethanol, and organic solvents.[2]Acetaminophen is soluble in ninety-five percent of alcohol, thirteen parts of acetone, forty different parts of glycerol, and ten parts of methyl alcohol. Acetaminophen mixed with various kinds of aspirin remain stable in dry conditions, however if these ingredients are mixed, typically surrounded by some sort of moisture, the latter compound can be hydrolyzed (to split a bond within a molecule by adding water) in the existence of moisture. [3]
Then acetaminophen is created from the interplay of p-aminophenol and acetic anhydride, an aqueous solution. Acetaminophen is stable under typical and regular conditions. [2] It accords to a class of drugs that are recognized as analgesics, also known as pain-relievers, and antipyretics, which are known as fever-reducers. [4]
Although Acetaminophen is not a toxic drug, it is however, a toxic compound; also known as N-acetyl- p -benzoquinonimine, its created when it is perforated by enzymes that are from the liver. If this drug is taken in small dosages, it is capable of being detoxified and excreted out of the system; but if it is taken in large amounts and dosages, it can submerge the detoxification system in the body and begin to harm the liver by destroying it's tissue. [5]

  • Metabolism of Acetaminophen: Acetaminophen is mainly absorbed and digested in the liver of the body. In order to be properly metabolized, the acetaminophen must be bound to a sulphate molecule. The acetaminophen must also be bound to a glucuronide molecule, a process called glucuronidation. The acetaminophen must go through these two processes in order to be properly excreted from the liver. The acetaminophen and it's two compounds (glucuronide and sulphate molecules) are simply harmless. [6]

Synthetic Production

Tylenol rapid-release gels that contain Acetaminophen.


Acetaminophen occurs from the derivation of coal tar with a process called prostaglandins. [7] The synthetic production of acetaminophen is performed by connecting a 4-hydroxyacetophenone oxime with a Beckman rearrangement catalyst in an alkli alkanoate reaction solvent and making sure they are in close contact with one another. [6] This toxic compound is assembled while it is being broken down by different enzymes in the liver. Then after being divided and detoxified, the compound can now be excreted from the liver and be distributed throughout the body. [5]

*Acetaminophen's purpose: Acetaminophen collaborates with prostaglandins, which are used to send pain signals throughout the body and help increase fever. When the body is in pain or is becoming sick, it will send out chemical messengers (prostaglandins) in comeback of either the injury or sickness. Acetaminophen comes into play by reducing the pain by blocking the pain signals that are sent out. It is able to prevent the signals being sent out without altering anything else. It impedes prostaglandin synthesis more particularly in the cells of the (nervous system) and does not have quite as much of an effect on other tissues. [5]

Uses

Acetaminophen is mainly used as a pain-reliever. It can be connected and used for many different conditions and is also used to relieve fevers. It can abate pain from arthritis, although it does not have any actual effect on any inflammation or swelling of the joints. Acetaminophen is just as useful as aspirin, and is as effective as pills such as Motrin, which are also known as "non-steroidal antiinflammatory drugs". [4] It can also be used for a variety of other different aches and pains such as: headaches, muscle pain, back pain, arthritis, common flu symptoms, toothaches, and menstrual and premenstrual cramps. There are really no groups of people who should not take acetaminophen.[8]

  • Dosage Limit
    • Adults: The recommended amount of Acetaminophen for adults is two 500mg tablets (equal to 1 gram) every four to six hours, however not going over eight tablets. This allotment can go on for several days, however if pain relief is required for a lengthy period, doctor supervision is required.
    • Children: Children's dosages vary for each child, according to their age and the type of product (i.e- tylenol, motrin, asprin) they are using. However, in general, dosages are typically based off a single dose of 10mg of Acetaminophen per kilogram of bodyweight. This dosage can be repeated every four to six hours, although not transcending four doses every four to six hours. [3]
  • Overdose

Although the recommended amount of Acetaminophen for an adult is two 500 mg tablets, studies show that in order for liver damage to take place from a single dosage, fifteen grams (thirty tablets) of acetaminophen are needed. However, most hospitals prefer to allot a safety leeway and say that liver damage could occur at twenty-four tablets or 150mg per kilogram of bodyweight, whichever one is smaller. The overdose inception can be minimized for a person who is taking specific prescription medicines, someone who is an alcoholic, or someone who is severely malnourished. If the dosage amount is spread over a lengthy amount of time, the inception can be lengthened if the dose is being effectively digested.[3] Also, in order to avoid overdose, be sure to check and become aware of all other medications that are being consumed along with the Acetaminophen. The more drugs that are consumed wtih acetaminophen, the more significant liver damage is done. It also helps to record the amount of acetaminophen that is being consumed each time it is taken. An antidote, N-acetyl cysteine is often given to acetaminophen overdose patients. The antidote is typically given around sixteen hours after the consumption of the acetaminophen.[6]

  • Side Effects

There are little harmful side effects when taking acetaminophen, unless the recommended dosage amount is exceeded. Many of the side effects include: loss of appetite, diarrhea, vomiting, nausea, sweating, irritability, yellow pigment of the skin and eyes, both liver and kidney failure, heart problems, coma, and could also have fatal effects as well if too much acetaminophen is consumed. Uncommon and rare, however extremely possible, ulcers or some internal bleeding in the digestive tract. However this is not very common and rarely is seen. [9]

Liver Damage

In taking acetaminophen, it is crucial one reads the prescription bottles with the dosage amounts on it. Any damage that is done to the liver from acetaminophen is all from dose-related manners. Any liver damage done from overdose on acetaminophen is a crucial matter due to the severity of the damage and the more the damage the more likely liver failure and death are the results. In both the United States and United Kingdom, acetaminophen overdose is the key cause of acute liver failure (rapid onset). In order for the liver to experience overdose, a huge amount of acetaminophen is required in the liver. Then the boundless amount of acetaminophen will begin to drown or saturate the sulphation and glucuronidation pathways. After this takes place, the acetaminophen is forced to be absorbed and metabolized through another pathway, which is the cytochrome P-450 system. One the cytochrome P-450 system begins to absorb the acetaminophen, it creates an intermediate metabolite called NAPQI. This is a toxic compound that is dangerous to the cytochrome P-450 system. Despite it's toxicity, the NAPQI is detoxified by the glutathione system if acetaminophen is digested properly. [6]

If Acetaminophen toxicity is suspected then the person should be seen by a [physician]] right away. It is also important to bring all prescription pills and bottles of acetaminophen with them. If overdose is assumed, then a doctor will typically gavage (pump) the stomach in order to excrete the pill particles. If a patient has overdosed on acetaminophen and other drugs as well then a physician might be forced to result to fixing the patient with activated charcoal. The activated charcoal binds and stops the several different medications from being carried throughout the body and serving their purpose. There are some speculations that the activated charcoal will also bind and prevent the acetaminophen antidote from working against the acetaminophen, which causes a problem. It will stop all the other drugs from working, except the acetaminophen. [6]

References

  1. Paracetmol By assistpainrelief.org
  2. 2.0 2.1 Acetaminophen (PARACETAMOL) By chemicalland21.com
  3. 3.0 3.1 3.2 Paracetamol Information Centre By British National Formulary, Vol 40; September 2000
  4. 4.0 4.1 Acetaminophen (side effects) By www.medicinenet.com, Jay W. Marks, M.D.
  5. 5.0 5.1 5.2 Acetaminophen Structure By www.chemistryexplained.com, Kyle Knight
  6. 6.0 6.1 6.2 6.3 6.4 Liver Damage By medicinenet.com
  7. Acetaminophen By Questia
  8. Acetaminophen Overview By Kristi Monson, M.D.
  9. Acetaminophen Side Effects By www.pain.emedtv.com