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.

Chemical data

Formula: C17H15NO5
Molecular weight: 313.3 g/mol
IUPAC name: (4-acetamidophenyl) 2-acetyloxybenzoate
SMILES: CC(=O)NC1=CC=C(C=C1)OC(=O)C2=CC=CC=C2OC(=O)C
InChIKey: FEJKLNWAOXSSNR-UHFFFAOYSA-N
XLogP: 2.2
Polar surface area: 81.7 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Indications: pain, Fever

via ChEMBL · EBI

Research

18 papers

[Long-term toxicity of benorylate].Zeitschrift fur Rheumatologie · 1975
Determination of benorilate in pharmaceutical formulations and its metabolite in urine at carbon paste electrode modified by silver nanoparticles.Talanta · 2005
[Identification and quantitation of impurities from benorilate (Salipran) by high-performance liquid chromatography (author's transl)].Journal of chromatography · 1977
Descriptors for some compounds with pharmacological activity; calculation of properties.International journal of pharmaceutics · 2022
[Studies on formulation and bioavailability of benorilate tablets].Yao xue xue bao = Acta pharmaceutica Sinica · 1994

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Wikidata facts

Subclass of: chemical compound
Mass: 313.095

Show 5 more facts

chemical formula: C₁₇H₁₅NO₅
canonical SMILES: CC(=O)NC1=CC=C(C=C1)OC(=O)C2=CC=CC=C2OC(=O)C
isomeric SMILES: C/C(=N\C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2OC(=O)C)/O
subject has role: analgesic
Commons category: Benorilate

Sources (2)

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Encyclopedic overview

2 sections

Contents

Synthesis
References

==Synthesis== Acetylsalicoyl chloride (1) condenses with paracetamol (2) to give benorilate (3).

Excerpted from Wikipedia’s “benorilate” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

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