Nucleophilic Addition of Bisulfite Ion to Prostaglandins E2 and A2: Implication in Aqueous Stability

Cho, M.J.; Krueger, William C.; Oesterling, T.O.

doi:10.1002/jps.2600660204

Journal of Pharmaceutical Sciences

1977

DOI: 10.1002/jps.2600660204

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Nucleophilic Addition of Bisulfite Ion to Prostaglandins E2 and A2: Implication in Aqueous Stability

M.J. Cho

William C. Krueger

T.O. Oesterling

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Cited by 6 publications

(1 citation statement)

References 36 publications

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“…[7][8][9][10] Limaprost alfadex is an inclusion complex of Limaprost, which is a prostaglandin E 1 derivative, and α-cyclodextrin (α-CD). [11][12][13] Tablets containing Limaprost alfadex are stable for three or more years at room temperature in a blister with an aluminum bag package containing a desiccant (airtight conditions).…”

mentioning

confidence: 99%

Stabilizing Effect of β-Cyclodextrin on Limaprost, a PGE<sub>1</sub> Derivative, in Limaprost Alfadex Tablets (Opalmon®) in Highly Humid Conditions

Inoue

Sekiya

Katayama

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Stabilization against humidity of Limaprost (a prostaglandin E 1 derivative), which is currently marketed as Opalmon ® , was undertaken using β-cyclodextrin (β-CD). Aqueous solutions of Limaprost alfadex/dextran 40 were lyophilized with and without β-CD. Limaprost alfadex lyophilized with β-CD was more chemically stable in humid conditions than that without β-CD. Moreover, the addition of β-CD as an excipient to tablets of these lyophilized composites remarkably improved the stability of Limaprost, and Limaprost in this moisture-resistant formulation was chemically stable for 19 weeks at 30°C, 75% relative humidity (R.H.). Chemical analysis of Limaprost and its degradation products indicated that degradation proceeded in the inclusion form (i.e., within the CD cavity). Solid 2 H-NMR spectroscopic studies showed that β-CD constrained the molecular mobility of water in the solid state. These results suggested that the stabilization of Limaprost by β-CD was at least partly due to the restricted molecular mobility of water, which acted as a catalytic species for the degradation, and also to the protection of the five-membered ring of Limaprost from water catalytic dehydration through inclusion complex formation with β-CD.

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confidence: 99%

Stabilizing Effect of β-Cyclodextrin on Limaprost, a PGE<sub>1</sub> Derivative, in Limaprost Alfadex Tablets (Opalmon®) in Highly Humid Conditions

Inoue

Sekiya

Katayama

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Quantitative assessment of the negative catalytic effects of a cationic surfactant myristyl-γ-picolinium chloride on the specific-acid catalyzed epimerization of 15(S)-15-methyl prostaglandin F2α

Cho

Allen

1978

International Journal of Pharmaceutics

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Reversed-phase high-performance liquid chromatography for simultaneous determination of prostaglandins E2, A2 and B2

Lee

Song

et al. 1994

International Journal of Pharmaceutics

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Nucleophilic Addition of Bisulfite Ion to Prostaglandins E2 and A2: Implication in Aqueous Stability

Cited by 6 publications

References 36 publications

Stabilizing Effect of β-Cyclodextrin on Limaprost, a PGE<sub>1</sub> Derivative, in Limaprost Alfadex Tablets (Opalmon®) in Highly Humid Conditions

Stabilizing Effect of β-Cyclodextrin on Limaprost, a PGE<sub>1</sub> Derivative, in Limaprost Alfadex Tablets (Opalmon®) in Highly Humid Conditions

Quantitative assessment of the negative catalytic effects of a cationic surfactant myristyl-γ-picolinium chloride on the specific-acid catalyzed epimerization of 15(S)-15-methyl prostaglandin F2α

Reversed-phase high-performance liquid chromatography for simultaneous determination of prostaglandins E2, A2 and B2

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