Benorilate

Benorilate
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 InfoCard100.023.340 Edit 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) X markN
  • Key:FEJKLNWAOXSSNR-UHFFFAOYSA-N X markN
 X markNcheckY (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.

It was originally introduced as a less-irritating ester of aspirin. Unlike aspirin and paracetamol, benorilate has no taste, though ethanol-based preparations may contain a slight smell of wintergreen from ethyl salicylate impurities.

Synthesis

Acetylsalicoyl chloride (1) condenses with paracetamol (2) to give benorilate (3).

Synthesis of benorilate

Alkaline hydrolysis of the acetyl ester moiety of benorilate yields another pharmaceutical, acetaminosalol (phenetsal): the ester of salicylate and paracetamol.

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. ↑ Croft DN, Cuddigan JH, Sweetland C (September 1972). "Gastric bleeding and benorylate, a new aspirin". British Medical Journal. 3 (5826): 545–547. doi:10.1136/bmj.3.5826.545. PMC 1785865. PMID 4560728.
  3. ↑ Livingstone JL (1 January 1973). "Benorylate Pharmaceutics". Rheumatology. XII (suppl): 16–20. doi:10.1093/rheumatology/XII.suppl.16.
  4. ↑ Kleemann A, Kutscher B, Reichert D, Bossart M. "Benorilate". Pharmaceutical Substances. Thieme. Retrieved July 18, 2025.
  5. ↑ NL6504517 idem Andrew Robertson, US patent 3431293, Robertson A, Andrew R, "Amino-Phenol Compounds", published 1969-03-04, issued 1969-03-04, assigned to Sterling Drug Inc and Sterling Drug Inc. (1969 to Sterling Drug Inc)
  6. ↑ Mario Portelli & Giorgio Renzi, DE 2402231, Portelli MI, Renzi GI, "Verfahren zur Herstellung von Benorilat", published 1974-08-01, issued 1978-03-30, assigned to Whitefin Holding SA and Whitefin Holding s.a., Lugano (Schweiz) (1974 to Whitefin Holding SA)
  7. ↑ Huang Xiaocheng, et al. CN 111056968, Huang X, Zhang B, Su H, Lin H, 黄晓程 张, 粟晖 林, "Preparation method of benorilate", published 2020-04-24, issued 2023-04-14, assigned to Univ Guangxi Sci & Technology and 广西科技大学 (2020 to Guangxi University of Science and Technology)
  8. ↑ 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.