Aspirin—A national survey III: Determination of impurities in bulk aspirin and aspirin formulations by high-pressure liquid chromatography and spectrophotometry

Kirchhoefer, Ross D; Reepmeyer, John C.; Juhl, William E.

doi:10.1002/jps.2600690519

Cited by 17 publications

(11 citation statements)

References 13 publications

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“…The second type utilizes an existing tablet dissolution apparatus that provides a wire mesh basket for holding the sample (16)(17)(18)(19)(20)(21)(22). The third and fourth types employ a membrane; the third consists of a sample chamber separated from a reservoir by a membrane (23-33), whereas the fourth employs dialysis tubing or a natural membrane (33-46).…”

Section: Accepted For Publicationmentioning

confidence: 99%

“…Unfortunately, in their solvent system, both salicylic acid and salicylamide excite and fluoresce at virtually the same wavelengths. Other methods involving chromophore-forming reactions (19) and high-pressure liquid chromatographic separations (20,21) were proposed but never evaluated for interference by other sample constituents common in multicomponent preparations.…”

mentioning

confidence: 99%

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Spectrofluorometric Determination of Acetylsalicylic Acid, Salicylamide, and Salicylic Acid as an Impurity in Pharmaceutical Preparations

Street

Schenk

1981

Journal of Pharmaceutical Sciences

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Section: Accepted For Publicationmentioning

confidence: 99%

mentioning

confidence: 99%

Spectrofluorometric Determination of Acetylsalicylic Acid, Salicylamide, and Salicylic Acid as an Impurity in Pharmaceutical Preparations

Street

Schenk

1981

Journal of Pharmaceutical Sciences

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“…It is this phenomenon that accounts for the instability of aspirin in the pharmaceutical preparations (2). According to an extensive survey of aspirin tablets (6), levels of salicylic acid can be similar to those of acetylsalicylic acid, and under certain conditions a large number of other products can be formed (6)(7)(8)(9).…”

mentioning

confidence: 99%

Spectrophotometric determination of aspirin by trans acetylation of 4-aminophenol

Verma¹,

Jain²

1986

Anal. Chem.

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Aspirin transacetylates 4-amlnophenol, yielding acetamlnophen (N-acetyl-4-amlnophenoI), whlch can be determined by Its Oxidation to an orange-yellow product either by lodylbenzene In acetone when the absorbance is measured at 430 nm or by photometric titration with 2-lodylbenzoate In acetone-water medium at 444 nm. Sallcyllc acid, salicylamide, oxyphenbutazone, caffeine, and sodlum hydrogen carbonate do not Interfere. Drug mixtures of acetaminophen and aspirin have been analyzed by determlnlng acetaminophen alone dlrectly wHh lodyl reagents and then determlnlng acetamlnophen plus asplrln afler 4-amlnophenol reactlon; aspirln Is found by difference.As an aromatic ester, aspirin (acetylsalicylic acid) has a good leaving group and is thus relatively susceptible to hydrolysis to salicylic and acetic acids (1-3) and other acyl transfer reactions, the catalytic effect being shown by the ortho carboxyl group and by the presence of moisture or basic substances (4, 5). It is this phenomenon that accounts for the instability of aspirin in the pharmaceutical preparations (2). According to an extensive survey of aspirin tablets (6), levels of salicylic acid can be similar to those of acetylsalicylic acid, and under certain conditions a large number of other products can be formed (6-9).In recent formulations aspirin is dispensed with acetaminophen, caffeine, and oxyphenbutazone. Methods, e.g., titration with a base in nonaqueous media (lo), nitrozation followed by alkalization (11), and bromimetry (12) are general reactions and cannot be used in the presence of salicylic acid or for compound tablets. Colorimetry (13), fluorometry (5), GC (14,15), and room-temperature phosphorimetry (16) have been used in many methods but HPLC is convenient for monitoring salicylic acid simultaneously with aspirin and other active ingredients (1 7-20). Conversion of aspirin into salicylic acid during sample preparation is a vexing problem and it can limit the accuracy of determination. Attempts to obviate or minimize errors from this source include injection of sample within a few minutes of its preparation (21), extrapolation of results back to time zero (51, preparation of calibrated standards with matching amounts of aspirin (7), selection of solvents to minimize salicylic acid formation (4,20,22), and separation of aspirin from product ingredients that accelerate its degradation (22). Complex formulations have been analyzed by ultraviolet absorption after separation of their constituents by partition chromatography (23-25).During a project to analyze multicomponent drugs without preseparation of their constituents (26-31), we aimed to determine aspirin in the presence of salicylic acid and other active constituents of drug formulations.

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“…The recent investigations of Reepmeyer and Kirchhoefer (1,2) on the isolation and quantification of trace impurities in aspirin illustrate such an undertaking. 4-Acetyl-2-(2'-hydroxyethyl) -5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one (11) is an antihypertensive agent prepared as illustrated in Scheme I.…”

mentioning

confidence: 99%

Isolation and Identification of Impurities in 4-Acetyl-2-(2′-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one, an Antihypertensive Agent

Powersx¹,

Eckert²,

Gehrlein³

1981

Journal of Pharmaceutical Sciences

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Aspirin—A national survey III: Determination of impurities in bulk aspirin and aspirin formulations by high-pressure liquid chromatography and spectrophotometry

Cited by 17 publications

References 13 publications

Spectrofluorometric Determination of Acetylsalicylic Acid, Salicylamide, and Salicylic Acid as an Impurity in Pharmaceutical Preparations

Spectrofluorometric Determination of Acetylsalicylic Acid, Salicylamide, and Salicylic Acid as an Impurity in Pharmaceutical Preparations

Spectrophotometric determination of aspirin by trans acetylation of 4-aminophenol

Isolation and Identification of Impurities in 4-Acetyl-2-(2′-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one, an Antihypertensive Agent

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