Amino acids as co-amorphous stabilizers for poorly water soluble drugs – Part 1: Preparation, stability and dissolution enhancement

Löbmann, Korbinian; Grohganz, Holger; Laitinen, Riikka; Strachan, Clare J.

doi:10.1016/j.ejpb.2013.03.014

Cited by 255 publications

(245 citation statements)

References 32 publications

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“…The results obtained from the FTIR and XRPD measurements of co-amorphous AA-IND mixtures prepared by cryomilling were very similar to the results reported by Löbmann et al, which suggests that as long as the milling temperature is kept low, either by cryomilling or by milling in a cold room, the end product is amorphous, and the interactions between molecules remain similar [24,25]. Different preparation methods and even the same methods with different conditions, however, have been shown to affect structural and thermal properties (such as T g ) of amorphous IND, and these may account for the differences between the T g s of ball milled and cryomilled materials [24,25,35,36].…”

Section: Discussionsupporting

confidence: 77%

“…Thermal analysis with DSC indicated that the co-amorphous AA-IND mixtures were homogenous mixtures, since only one glass transition was present in each thermogram. T g s measured in this study; however, differed slightly from the values measured by Löbmann et al (Table 2) [24].…”

Section: Solid State Analysis Of the Cryomilled Materialscontrasting

confidence: 55%

“…Löbmann et al studied the ability of carbamazepine and indomethacin (IND) to form co-amorphous mixtures with arginine (ARG), tyrosine, phenylalanine (PHE) and tryptophan (TRP) [24]. They noted that both drugs formed co-amorphous blends with suitable amino acids.…”

mentioning

confidence: 99%

“…By the definition of Dengale et al, these systems contain two or more small molecular weight compounds that are homogenously mixed to form an amorphous single phase system [19]. For example, two active compounds have been combined to produce co-amorphous mixtures [20,21], but finding compatible drug-drug pairs may, however, be challenging, which has increased the interest in combining a pharmacologically active molecule with an inactive low molecular weight excipient, such as an amino acid (AA) [22][23][24].…”

mentioning

confidence: 99%

“…The present study examined in detail the dissolution properties of ARG-IND, PHE-IND and TRP-IND co-amorphous mixtures, which were prepared using similar methods as described by Löbmann et al [24,25]. The aim was to investigate whether the AAs would be able to act as molecular parachutes and prolong the supersaturated state of amorphous IND in simple buffer solutions (pH 5.0 and 6.5) as well as in biorelevant solutions (FaSSIF (pH 6.5) and FeSSIF (pH 5.0), which have rarely been applied in dissolution studies with (co-)amorphous formulations [26].…”

mentioning

confidence: 99%

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Dissolution behavior of co-amorphous amino acid-indomethacin mixtures: The ability of amino acids to stabilize the supersaturated state of indomethacin

Ojarinta

Heikkinen

Sievänen

et al. 2017

European Journal of Pharmaceutics and Biopharmaceutics

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Dissolution behavior of co-amorphous amino acid-indomethacin mixtures : The ability of amino acids to stabilize the supersaturated state of indomethacin Ojaranta, Rami; Heikkinen, Aki T.; Sievänen, Elina; Laitinen, Riikka Ojaranta, R., Heikkinen, A. T., Sievänen, E., & Laitinen, R. (2017). Dissolution behavior of co-amorphous amino acid-indomethacin mixtures : The ability of amino acids to stabilize the supersaturated state of indomethacin. European Journal of Pharmaceutics and Biopharmaceutics, 112, 85-95. doi:10.1016/j.ejpb.2016.11 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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Section: Discussionsupporting

confidence: 77%

Section: Solid State Analysis Of the Cryomilled Materialscontrasting

confidence: 55%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Dissolution behavior of co-amorphous amino acid-indomethacin mixtures: The ability of amino acids to stabilize the supersaturated state of indomethacin

Ojarinta

Heikkinen

Sievänen

et al. 2017

European Journal of Pharmaceutics and Biopharmaceutics

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Amorphous Solid Dispersion Screening

Newman¹

2015

Pharmaceutical Sciences Encyclopedia

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Finding the optimal form for drug development can involve a number of different screening activities, including a search for polymorphs, salts, cocrystals, and/or amorphous solid dispersions. High‐risk compounds will require special formulations that include amorphous solid dispersions. An amorphous dispersion screen is performed to find a suitable amorphous dispersion that exhibits acceptable properties. The screening performed in early development may focus on parameters such as solubility, supersaturation, short‐term physical and chemical stability, and animal bioavailability to get into early‐phase clinical trials quickly and establish proof of concept. Before starting an amorphous dispersion screen project, information on the active pharmaceutical ingredient (API) is needed. This may include chemical structure, solid form, physical stability, chemical stability, log P, hydrogen bond donors/acceptors, calculated solubility parameters, and known solubilities of the solid in various solvents/biorelevant media.

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Cocrystals, Coamorphous Phases and Coordination Complexes of γ‐ andε‐Lactams

Hall

Chambers

Musa

et al. 2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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The strongly interacting lactam functional group in both γand ε-lactams makes them of considerable interest in the formation of multicomponent solids including a hugely diverse range of cocrystals, coordination complexes with lactam ligands and coamorphous phases. Cocrystals are structurally homogenous crystalline substances that are comprised of two or more chemically different neutral molecules generally in stoichiometric amounts that are connected by non-ionic and non-covalent interactions [1]. The Food and Drug Administration (FDA) classifies cocrystals as crystalline materials composed of two or more different molecules, typically Active Pharmaceutical Ingredients (API) and approved, non-toxic cocrystal former (coformer), in the same crystal lattice [2].Cocrystals fall under the umbrella of multi-component molecular solids, which encompasses crystalline forms such as solvates, hydrates, and lattice inclusion compounds as well as coamorphous materials. The relationships between these various solid forms are illustrated in Figure 1. Also included under multi-component crystalline solids are solid solutions in which one component is randomly distributed in a crystal of another [4]. Salts are also multi-component molecular solids, with the main difference between a salt and a cocrystal often being proton transfer from an acid to a base that occurs to give a salt in contrast to neutral molecule cocrystals. However, the distinction is a fine one since, depending on the temperature, salts and cocrystals can interconvert [5]. Generally, true cocrystals are regarded as being formed from components that are solids at room temperature, a definition which excludes solvates and hydrates. However, this narrowing would mean that some materials involving low melting solids might be regarded as cocrystals in some labs and not others despite that fact that there is no fundamental structural difference between a cocrystal and a solvate [1,6,7].

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Amino acids as co-amorphous stabilizers for poorly water soluble drugs – Part 1: Preparation, stability and dissolution enhancement

Cited by 255 publications

References 32 publications

Dissolution behavior of co-amorphous amino acid-indomethacin mixtures: The ability of amino acids to stabilize the supersaturated state of indomethacin

Dissolution behavior of co-amorphous amino acid-indomethacin mixtures: The ability of amino acids to stabilize the supersaturated state of indomethacin

Amorphous Solid Dispersion Screening

Cocrystals, Coamorphous Phases and Coordination Complexes of γ‐ andε‐Lactams

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