Stability of Aspirin in Liquid and Semisolid Bases I: Substituted and Nonsubstituted Polyethylene Glycols

Whitworth, Clyde W.; Jun, H. W.; Luzzi, L.A.

doi:10.1002/jps.2600620726

Cited by 14 publications

(2 citation statements)

References 3 publications

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“…100,[256][257][258][259][260] Though these reaction products may be ultimately hydrolyzed back to their parent compounds in the GIT, the bioavailabilities of the parent compounds could be reduced significantly. 100,[256][257][258][259][260] Though these reaction products may be ultimately hydrolyzed back to their parent compounds in the GIT, the bioavailabilities of the parent compounds could be reduced significantly.…”

Section: Reactions Between Encapsulated Compounds and Excipientsmentioning

confidence: 99%

“…100 In addition, as esterification and hydrolytic reactions are generally reversible, hydrolysis of the formed esters back to the parent compounds could be potentially achieved through increasing the amount of available water in the fill formulation. 256,257,263 These transesterification reactions were shown to be affected by temperature (rate at 608C > 458C > 278C > 48C) and the number of hydroxyl reactive sites available on the polymer chain (rate in PEG > methoxyPEG > PEG acetate). 98,100,258 The decomposition of aspirin in polyethylene glycols in the absence of water was also attributed to the transesterification reactions, resulting in the formation of salicylic acid and acetylated polyethylene glycols.…”

Section: Reactions Between Encapsulated Compounds and Excipientsmentioning

confidence: 99%

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Soft Gelatin Capsules (Softgels)

Gullapalli

2010

Journal of Pharmaceutical Sciences

111

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Section: Reactions Between Encapsulated Compounds and Excipientsmentioning

confidence: 99%

Section: Reactions Between Encapsulated Compounds and Excipientsmentioning

confidence: 99%

Soft Gelatin Capsules (Softgels)

Gullapalli

2010

Journal of Pharmaceutical Sciences

111

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Zum Mechanismus der Umesterung des Aspirins mit Polyäthylenglykolen

Eckert

Zander

1977

Archiv der Pharmazie

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Eckert und ZanderArch. Pharm.Reinigung an Kieselgel H mit Methanol/Chloroform (5 + 95) als Fliefimittel werden die nach dem Eindampfen des Eluats zuriickbleibenden Kristalle zunachst aus Methanol-Chloroform und dann aus Methanol-Wasser umkristallisiert.Es werden Untcrsuchungen zum Mechanismus der hohen Umesterungsgeschwindigkeit des Aspirins rnit Polyathylenglykolen beschrieben. Die Helixstruktur der Polyathylenglykole fuhrt zu einer hohen Elektronegativitat der Athersauerstoffatome, die katalytisch die Umesterung der Ester-Carbonylgruppe mit den endstandigen Hydroxylgruppen der Polyathylenglykole beschleunigen. Die Reaktion verlauft bimolekular. Dies l a t darauf schlieben, dab eine besondere sterische Anordnung f~ die Umesterung erforderlich ist, etwa derart, dab Hydroxylgruppe und basenkatalytisch wirksame Athersauerstoffatome in Nachbarstellung zueinander stehen. Mechanism of Transesterification of Aspirin with PolyethyleneglycolsThe helix structure of polyethyleneglycols results in a high electronegativity of the ether oxygen, which catalytically accelerates transesterification between the ester group of aspirin and the terminal hydroxy groups of polyethyleneglycols. The reaction is bimolecular. This suggests that special steric relations are necessary for rapid transesterification, such as the neighbourhood of the catalytically active ether oxygen atoms and the terminal hydroxy group.Es ist seit langem bekannt, da8 Aspirin mit Polyathylenglykolen leicht ~r n e s t e r t '~~) . Die im pH-Bereich von 5-8 ebenfalls leicht erfolgende H y d r o 1 y s e des Aspirins verlauft nach Untersuchungen von Garrett4) uber eine aktivierte Zwischenstufe.

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Pharmaceutical Sciences — 1973: Literature Review of Pharmaceutics

Herd¹,

Haleblian²

1974

Journal of Pharmaceutical Sciences

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Stability of Aspirin in Liquid and Semisolid Bases I: Substituted and Nonsubstituted Polyethylene Glycols

Cited by 14 publications

References 3 publications

Soft Gelatin Capsules (Softgels)

Soft Gelatin Capsules (Softgels)

Zum Mechanismus der Umesterung des Aspirins mit Polyäthylenglykolen

Pharmaceutical Sciences — 1973: Literature Review of Pharmaceutics

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