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Benorilate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Benorilate
Clinical data
Routes of
administration
Oral
ATC code
Identifiers
  • 4-acetamidophenyl 2-(acetyloxy)benzoate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.023.340Edit this at Wikidata
Chemical and physical data
FormulaC17H15NO5
Molar mass313.309 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) ☒N
  • Key:FEJKLNWAOXSSNR-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Benorilate (INN), orbenorylate, is anester-linkedcodrug ofaspirin withparacetamol. It is used as ananti-inflammatory andantipyretic 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 aboutReye syndrome.[1]

Synthesis

[edit]

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

Synthesis of benorilate

Partialsaponification of benorilate leads toacetaminosalol (phenetsal).[6]

References

[edit]
  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.
Opioids
Opiates/opium
Semisynthetic
Synthetic
Paracetamol-type
NSAIDs
Propionates
Oxicams
Acetates
COX-2 inhibitors
Fenamates
Salicylates
Pyrazolones
Others
Cannabinoids
Ion channel
modulators
Calcium blockers
Sodium blockers
Potassium openers
Myorelaxants
Others
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others


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