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	N02BA10 (WHO)
Identifiers
IUPAC name 4-acetamidophenyl 2-(acetyloxy)benzoate
CAS Number	5003-48-5 N
PubChem CID	21102
ChemSpider	19846 N
UNII	W1QX9DV96G
ChEMBL	ChEMBL162036 N
CompTox Dashboard (EPA)	DTXSID5022649
ECHA InfoCard	100.023.340
Chemical and physical data
Formula	C17H15NO5
Molar mass	313.309 g·mol−1
3D model (JSmol)	Interactive image
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

Acetylsalicoyl chloride (1) condenses with paracetamol (2) to give benorilate (3).^[2][3][4][5]

Synthesis of benorilate

Alkaline hydrolysis of the acetyl ester moiety of benorilate yields another pharmaceutical, acetaminosalol (phenetsal).^[6]