Benorilate

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]

Benorilate
Clinical data
Routes of
administration		Oral
ATC code
Identifiers
IUPAC name
  • 4-acetamidophenyl 2-(acetyloxy)benzoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.023.340
Chemical and physical data
FormulaC17H15NO5
Molar mass313.309 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C)Oc2ccccc2C(=O)Oc1ccc(NC(C)=O)cc1
InChI
  • 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
 NY (what is this?)  (verify)

Synthesis
Thieme Patents:[2][3] Sino:[4]

Acetyl salicoyl chloride [5538-51-2] (1) is reacted with paracetamol (2) to give benorilate (3).

Saponification of the ester led to Acetaminosalol (Phenetsal) [118-57-0].[5]

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. NL6504517 idem Andrew Robertson, U.S. Patent 3,431,293 (1969 to Sterling Drug Inc).
  3. Mario Portelli & Giorgio Renzi, DE 2402231 (1974 to Whitefin Holding SA).
  4. Huang Xiaocheng, et al. CN 111056968 (2020 to Guangxi University of Science and Technology).
  5. 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.
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