Benorilate

Last updated
Benorilate
Benorilate.svg
Clinical data
Routes of
administration
Oral
ATC code
Identifiers
  • 4-acetamidophenyl 2-(acetyloxy)benzoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.023.340 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H15NO5
Molar mass 313.309 g·mol−1
3D model (JSmol)
  • O=C(C)Oc2ccccc2C(=O)Oc1ccc(NC(C)=O)cc1
  • InChI=1S/C17H15NO5/c1-11(19)18-13-7-9-14(10-8-13)23-17(21)15-5-3-4-6-16(15)22-12(2)20/h3-10H,1-2H3,(H,18,19) X mark.svgN
  • Key:FEJKLNWAOXSSNR-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Benorilate (INN), or benorylate, is an ester-linked codrug of aspirin with paracetamol. It is used as an anti-inflammatory and antipyretic medication. In the treatment of childhood fever, it has been shown to be inferior to paracetamol and aspirin taken separately. In addition, because it is converted to aspirin, benorylate is not recommended in children due to concerns about Reye syndrome. [1]

Synthesis

Acetyl salicoyl chloride (1) is reacted with paracetamol (2) to give benorilate (3). [2] [3] [4] [5]

Synthesis of benorilate Benorilate synthesis.svg
Synthesis of benorilate

Partial saponification of benorilate leads to acetaminosalol (phenetsal). [6]

Related Research Articles

<span class="mw-page-title-main">Aspirin</span> Medication

Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever.

<span class="mw-page-title-main">Nonsteroidal anti-inflammatory drug</span> Class of therapeutic drug for relieving pain and inflammation

Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

An antipyretic is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which results in a reduction in fever.

<span class="mw-page-title-main">Fever</span> Raised body temperature due to disease

Fever or pyrexia in humans is a body temperature above the normal range due to an increase in the body's temperature set point in the hypothalamus. There is no single agreed-upon upper limit for normal temperature: sources use values ranging between 37.2 and 38.3 °C in humans. The increase in set point triggers increased muscle contractions and causes a feeling of cold or chills. This results in greater heat production and efforts to conserve heat. When the set point temperature returns to normal, a person feels hot, becomes flushed, and may begin to sweat. Rarely a fever may trigger a febrile seizure, with this being more common in young children. Fevers do not typically go higher than 41 to 42 °C.

<span class="mw-page-title-main">Paracetamol</span> Common medication for pain and fever

Paracetamol is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely used over the counter medication. Common brand names include Tylenol and Panadol.

<span class="mw-page-title-main">Ibuprofen</span> Medication used for treating pain, fever, and inflammation

Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used orally or intravenously. It typically begins working within an hour.

<span class="mw-page-title-main">Phenacetin</span> Pharmaceutical drug

Phenacetin is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s.

Anti-inflammatory or antiphlogistic is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as opposed to opioids, which affect the central nervous system to block pain signaling to the brain.

<span class="mw-page-title-main">Acetanilide</span> Chemical compound

Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.

Cyclooxygenase-3 (COX-3) is an enzyme that is encoded by the PTGS1 (COX1) gene, but is not functional in humans. COX-3 is the third and most recently discovered cyclooxygenase (COX3050) isozyme, while the first two to be discovered were COX-1 and COX-2. The COX-3 isozyme is encoded by the same gene as COX-1, with the difference that COX-3 retains an intron that is not retained in COX-1.

<span class="mw-page-title-main">Phenazone</span> Chemical compound

Phenazone is an analgesic, antipyretic and anti-inflammatory drug. While it predates the term, it is often classified as a nonsteroidal anti-inflammatory drug (NSAID). Phenazone was one of the earliest synthetic medications — when it was patented in 1883, the only synthetic medical chemicals on the market were chloral hydrate, a sedative, trimethylamine, and iodol (tetraiodopyrrol), an early antiseptic. One of the earliest widely used analgesics and antipyretics, phenazone was gradually replaced in common use by other medications including phenacetin, aspirin, paracetamol and modern NSAIDs such as ibuprofen. However, it is still available in several countries either as an over-the-counter or prescribed drug.

<span class="mw-page-title-main">Butalbital</span> Barbiturate drug used for headaches

Butalbital is a barbiturate with an intermediate duration of action. Butalbital is often combined with other medications, such as paracetamol (acetaminophen) or aspirin, for the treatment of pain and headache. The various formulations combined with codeine are FDA-approved for the treatment of tension headaches. Butalbital has the same chemical formula as talbutal but a different structure—one that presents as 5-allyl-5-isobutylbarbituric acid.

<span class="mw-page-title-main">Analgesic nephropathy</span> Medical condition

Analgesic nephropathy is injury to the kidneys caused by analgesic medications such as aspirin, bucetin, phenacetin, and paracetamol. The term usually refers to damage induced by excessive use of combinations of these medications, especially combinations that include phenacetin. It may also be used to describe kidney injury from any single analgesic medication.

<span class="mw-page-title-main">Propyphenazone</span> Chemical compound

Propyphenazone is a derivative of phenazone with similar analgesic and antipyretic effects. Originally patented in 1931, propyphenazone is marketed as a combination formulation with paracetamol and caffeine for treatment of primary headache disorder.

<span class="mw-page-title-main">Zomepirac</span> Withdrawn non-steroidal anti-inflammatory drug

Zomepirac is an orally effective nonsteroidal anti-inflammatory drug (NSAID) that has antipyretic actions. It was developed by McNeil Pharmaceutical, approved by the FDA in 1980, and sold as the sodium salt zomepirac sodium, under the brand name Zomax. Due to its clinical effectiveness, it was preferred by doctors in many situations and obtained a large share of the analgesics market; however, it was subsequently withdrawn in March 1983 due to its tendency to cause serious anaphylaxis in a small, but unpredictable, subset of the patient population.

<span class="mw-page-title-main">Fluproquazone</span> Chemical compound

Fluproquazone was a quinazolinone derivative with potent analgesic, antipyretic, and anti-inflammatory effects discovered by Sandoz. It was withdrawn during development due to liver toxicity.

<span class="mw-page-title-main">Cyclooxygenase-1</span>

Cyclooxygenase 1 (COX-1), also known as prostaglandin-endoperoxide synthase 1, is an enzyme that in humans is encoded by the PTGS1 gene. In humans it is one of two cyclooxygenases.

<span class="mw-page-title-main">Paracetamol poisoning</span> Toxicity due to paracetamol overdose

Paracetamol poisoning, also known as acetaminophen poisoning, is caused by excessive use of the medication paracetamol (acetaminophen). Most people have few or non-specific symptoms in the first 24 hours following overdose. These symptoms include feeling tired, abdominal pain, or nausea. This is typically followed by absence of symptoms for a couple of days, after which yellowish skin, blood clotting problems, and confusion occurs as a result of liver failure. Additional complications may include kidney failure, pancreatitis, low blood sugar, and lactic acidosis. If death does not occur, people tend to recover fully over a couple of weeks. Without treatment, death from toxicity occurs 4 to 18 days later.

<span class="mw-page-title-main">Clonixin</span> Nonsteroidal anti-inflammatory drug (NSAID)

Clonixin is a nonsteroidal anti-inflammatory drug (NSAID). It also has analgesic, antipyretic, and platelet-inhibitory actions. It is used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation.

Aspirin/paracetamol/caffeine is a combination drug for the treatment of pain, especially tension headache and migraine. It contains aspirin, a non-steroidal anti-inflammatory drug; paracetamol (acetaminophen), an analgesic; and caffeine, a stimulant.

References

  1. Similä S, Keinänen S, Kouvalainen K (December 1975). "Oral antipyretic therapy: evaluation of benorylate, an ester of acetylsalicylic acid and paracetamol". European Journal of Pediatrics. 121 (1): 15–20. doi:10.1007/bf00464391. PMID   2478. S2CID   21112438.
  2. Thieme
  3. NL6504517 idem Andrew Robertson, U.S. patent 3,431,293 (1969 to Sterling Drug Inc)
  4. Mario Portelli & Giorgio Renzi, DE 2402231 (1974 to Whitefin Holding SA)
  5. Huang Xiaocheng, et al. CN 111056968 (2020 to Guangxi University of Science and Technology)
  6. Moerk Nielsen, N., Bundgaard, H. (March 1989). "Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs". Journal of Medicinal Chemistry. 32 (3): 727–734. doi:10.1021/jm00123a040. PMID   2918521.