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Merck

Lactic acid oligomers (OLAs) as prodrug moieties.

Die Pharmazie (2013-03-09)
J Kruse, B Lachmann, R Lauer, S Eppacher, C R Noe
ABSTRACT

In this paper we propose the use of lactic acid oligomers (OLAs) as prodrug moieties. Two synthetic approaches are presented, on the one hand a non selective oligomerisation of lactic acid and on the other hand a block synthesis to tetramers of lactic acid. Dimers of lactic acid were investigated with respect to their plasma stability and their adsorption to albumine. Ibuprofen was chosen as the first drug for OLAylation. The ester 19 of LA(1)-ibuprofen was evaluated with respect to the degradation to human plasma and the adsorption to albumine. All results indicate that lactic acid oligomers are promising prodrug moieties.

MATERIALS
Product Number
Brand
Product Description

Supelco
Ibuprofen, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Ibuprofen, ≥98% (GC)
Supelco
Ibuprofen
Supelco
Ibuprofen sodium salt, ≥98% (GC)
Ibuprofen, European Pharmacopoeia (EP) Reference Standard
Ibuprofen for peak identification, European Pharmacopoeia (EP) Reference Standard
Supelco
Ibuprofen solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®
Sigma-Aldrich
(S)-(+)-Ibuprofen, ReagentPlus®, 99%