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 ;
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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.

Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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