{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 461759359 | IUPAC_name = 4-acetamidophenyl 2-(acetyloxy)benzoate | image = Benorilate.svg | image_class = skin-invert-image <!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = Oral <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 5003-48-5<!--from KEGG--> | ATC_prefix = N02 | ATC_suffix = BA10 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 162036 | PubChem = 21102 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = W1QX9DV96G | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 19846 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = FEJKLNWAOXSSNR-UHFFFAOYSA-N <!--Chemical data--> | C=17 | H=15 | N=1 | O=5 | smiles = O=C(C)Oc2ccccc2C(=O)Oc1ccc(NC(C)=O)cc1 }} '''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.<ref>{{cite journal | vauthors = Similä S, Keinänen S, Kouvalainen K | title = Oral antipyretic therapy: evaluation of benorylate, an ester of acetylsalicylic acid and paracetamol | journal = European Journal of Pediatrics | volume = 121 | issue = 1 | pages = 15–20 | date = December 1975 | pmid = 2478 | doi = 10.1007/bf00464391 | s2cid = 21112438 }}</ref>
==Synthesis== Acetylsalicoyl chloride ('''1''') condenses with paracetamol ('''2''') to give benorilate ('''3''').<ref>{{cite book | vauthors = Kleemann A, Kutscher B, Reichert D, Bossart M | chapter = Benorilate | title = Pharmaceutical Substances | publisher = Thieme | chapter-url = https://pharmaceutical-substances.thieme.com/lexicon/KD-02-0034 | access-date = July 18, 2025 }}</ref><ref>NL6504517 idem Andrew Robertson, {{US patent|3431293}} (1969 to Sterling Drug Inc)</ref><ref>Mario Portelli & Giorgio Renzi, {{Cite patent | DE | 2402231 }} (1974 to Whitefin Holding SA)</ref><ref>Huang Xiaocheng, et al. {{Cite patent | CN | 111056968 }} (2020 to Guangxi University of Science and Technology)</ref>
class=skin-invert-image|thumb|center|500px|Synthesis of benorilate
Alkaline hydrolysis of the acetyl ester moiety of benorilate yields another pharmaceutical, acetaminosalol (phenetsal).<ref>{{cite journal | vauthors = Moerk Nielsen N, Bundgaard H | title = Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs | journal = Journal of Medicinal Chemistry | volume = 32 | issue = 3 | pages = 727–734 | date = Mar 1989 | pmid = 2918521 | doi = 10.1021/jm00123a040 }}</ref>
== References == {{Reflist}}
{{Analgesics}} {{Anti-inflammatory and antirheumatic products}} {{Salicylates}} {{Prostanoidergics}}
Category:Analgesics Category:Antipyretics Category:Codrugs
{{musculoskeletal-drug-stub}} {{analgesic-stub}}