Co-crystal of Tramadol Hydrochloride–Celecoxib (<b>ctc</b>): A Novel API–API Co-crystal for the Treatment of Pain

Almansa, Carmen; MercÃ, Ramon; Tesson, Nicolas; Farran, Joan; s, Jaume TomÃ; Plata-SalamÃ¡n, Carlos R.

doi:10.1021/acs.cgd.6b01848

Cited by 122 publications

(100 citation statements)

References 51 publications

(73 reference statements)

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“…In addition, CTC susp displayed comparable efficacy to the morphine and oxycodone in this model but with an improved safety profile . Intrinsic dissolution studies have shown that the release profiles of tramadol and celecoxib from the co‐crystal are modified compared with those from each reference drug . Such effects have the potential to optimize the PK profiles, and thus efficacy and safety, of each API in CTC.…”

Section: Introductionmentioning

confidence: 94%

Pharmacokinetics of multiple doses of co‐crystal of tramadol–celecoxib: findings from a four‐way randomized open‐label phase I clinical trial

Videla

Lahjou

Vaqué

et al. 2017

Brit J Clinical Pharma

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AimWe compared the pharmacokinetic (PK) profiles of co‐crystal of tramadol–celecoxib (CTC) vs. each reference product (alone and in open combination) after single (first dose) and multiple dosing.MethodsHealthy adults aged 18–50 years received, under fasted conditions, 15 twice‐daily doses of the following treatments (separated by ≥14‐day washout): 200 mg immediate‐release (IR) CTC (equivalent to 88 mg tramadol and 112 mg celecoxib; treatment 1); 100 mg IR tramadol (treatment 2), 100 mg celecoxib (treatment 3); and 100 mg IR tramadol and 100 mg celecoxib (treatment 4). The treatment sequence was assigned by computer‐generated randomization. PK parameters were calculated using non‐compartmental analysis. Parameters for CTC were adjusted according to reference product dose.ResultsA total of 30 subjects (20 males, mean age 35 years) were included. Multiple‐dose tramadol PK parameters for treatments 1, 2 and 4, respectively, were 551, 632 and 661 ng ml−1 [mean maximum plasma concentration (C max)]; 4796, 4990 and 5284 ng h ml−1 (area under the plasma concentration–time curve over the dosing interval at steady state); and 3.0, 2.0 and 2.0 h (median time to C max at steady state). For treatments 1, 3 and 4, multiple‐dose celecoxib PK parameters were 445, 536 and 396 ng ml−1; 2803, 3366 and 2897 ng h ml−1; and 2.0, 2.0 and 3.0 h. Single‐dose findings were consistent with multiple‐dose data. Types of adverse events were consistent with known reference product safety profiles.ConclusionAfter single (first dose) and multiple dosing, PK parameters for each active pharmaceutical ingredient in CTC were modified by co‐crystallization compared with reference products alone or in open combination.

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Section: Introductionmentioning

confidence: 94%

Pharmacokinetics of multiple doses of co‐crystal of tramadol–celecoxib: findings from a four‐way randomized open‐label phase I clinical trial

Videla

Lahjou

Vaqué

et al. 2017

Brit J Clinical Pharma

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“…Potential of co-crystal design for molecules with limited H-bonding functionalities was demonstrated on the example of propyphenazone [221]: NH 2 , OH, and CO 2 H functionalities were found to be the most likely groups to interact with O=C group, and eight novel co-crystals were obtained using co-formers containing OH or/and CO 2 H groups. Dicarboxylic acids [222] or anions [223,224] can be applied to co-crystallize two molecules, which do not form co-crystals. acids demonstrate that it is still difficult to predict co-crystallization of small rigid molecules using this method [219].…”

Section: Co-crystals Designmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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“…# 2018 International Union of Crystallography Drug-drug complexes, salts and cocrystals play important roles in developing combinational drugs and fixed-dose combinations (Tiekink & Zukerman-Schpector, 2017). Almansa et al (2017) reported that the cocrystal of tramadol hydrochloride-celecoxib presented favorable physicochemical and dissolution properties. Putra et al (2016) suggested that a salt-type multicomponent crystal composed of gliclazide (GLI) and metformin (MET) presented higher solubility for GLI and lower hygroscopicity for MET.…”

Section: Issn 2052-5206mentioning

confidence: 99%

Triamterene–furosemide salt: structural aspects and physicochemical evaluation

Peng

Wang

Mei

2018

Acta Crystallogr Sect B

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Furosemide (Fur) is a BCS class IV diuretic drug with low bioavailability due to its poor solubility and poor membrane permeability. Triamterene (Tri) is a potassium-sparing diuretic with low bioavailability due to its poor solubility. Here, a novel drug-drug salt composed of Tri and Fur was successfully synthesized. Tri-Fur was comprehensively characterized with single-crystal X-ray and powder X-ray diffraction techniques, thermogravimetric analysis, differential scanning calorimetry and dynamic vapor sorption. The apparent equilibrium solubility (in pH 2.0 buffer) of Tri-Fur is improved compared with Fur and a physical mixture of Tri with equimolar Fur by 15.3-fold and 12.2-fold enhancements, respectively. Its intrinsic dissolution rate (in pH 2.0 buffer) is also higher than for a Fur component with an enhancement of 9.5-fold. This study provides a valuable insight into the formation of dual pharmaceutical salts and demonstrates that Tri-Fur can be a potential alternative formulation. short communications Acta Cryst. (2018). B74, 738-741 Peng, Wang and Mei Triamterene-furosemide salt 741

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Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Cited by 122 publications

References 51 publications

Pharmacokinetics of multiple doses of co‐crystal of tramadol–celecoxib: findings from a four‐way randomized open‐label phase I clinical trial

Pharmacokinetics of multiple doses of co‐crystal of tramadol–celecoxib: findings from a four‐way randomized open‐label phase I clinical trial

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Triamterene–furosemide salt: structural aspects and physicochemical evaluation

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