Benorilate

Benorilate
Clinical data
Routes of; administration	Oral
ATC code	N02BA10 (WHO) ;
Identifiers
	IUPAC name 4-acetamidophenyl 2-(acetyloxy)benzoate;
CAS Number	5003-48-5 ;
PubChem CID	21102;
ChemSpider	19846 ;
UNII	W1QX9DV96G;
ChEMBL	ChEMBL162036 ;
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) ; Key:FEJKLNWAOXSSNR-UHFFFAOYSA-N ;
	(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.^[1]

Synthesis

Acetyl salicoyl chloride (1) is reacted with paracetamol (2) to give benorilate (3).^[2]^[3]^[4]^[5]

Synthesis of benorilate

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

References

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

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[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] Thieme

[3] NL6504517 idem Andrew Robertson, U.S. patent 3,431,293 (1969 to Sterling Drug Inc)

[4] Mario Portelli & Giorgio Renzi, DE 2402231 (1974 to Whitefin Holding SA)

[5] Huang Xiaocheng, et al. CN 111056968 (2020 to Guangxi University of Science and Technology)

[6] 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.

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[2]

[3]

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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)