Benorilate Explained

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]}

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

References

1. Similä S, Keinänen S, Kouvalainen K . Oral antipyretic therapy: evaluation of benorylate, an ester of acetylsalicylic acid and paracetamol . European Journal of Pediatrics . 121 . 1 . 15–20 . December 1975 . 2478 . 10.1007/bf00464391 . 21112438 .
2. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0034 Thieme
3. NL6504517 idem Andrew Robertson, (1969 to Sterling Drug Inc)
4. Mario Portelli & Giorgio Renzi, (1974 to Whitefin Holding SA)
5. Huang Xiaocheng, et al. (2020 to Guangxi University of Science and Technology)
6. ((Moerk Nielsen, N.)), ((Bundgaard, H.)) . Journal of Medicinal Chemistry . Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs . 32 . 3 . 727–734 . March 1989 . 10.1021/jm00123a040. 2918521 .